Top Communities in Winter Park, FL

We have calculated the top communities in Winter Park based on the median sale prices of homes. The Winter Park community with the highest average home sale price was Camwood with an average of $6,300,000. All the Winter Park communities are listed below with links to view the homes for sale in the communities.

Camwood	$6,300,000
Tuscania	$4,430,000
Osceola Shores	$3,818,750
Woodmere Terrace	$3,537,500
Green Oaks	$3,450,000
Galloway Place	$3,237,500
Forrest Hills	$3,072,500
Sicilian Shores	$2,900,000
South Lakemont Shores	$2,800,000
Palmer Park	$2,650,000

Most Recent Homes for Sale in Winter Park

151 N Orlando Ave. ##115

1494 Westchester Ave.

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All Subdivisions/Condo Buildings in Winter Park

Community	Median Price
Alabama Condominiums Nestled along the serene shores of Lake Maitland, Florida, Alabama Condominiums offers a timeless lakeside retreat that captures the essence of historic elegance and modern comfort. This intimate community, comprising just 22 distinctive residences, invites residents to embrace a lifestyle of refined leisure with its array of thoughtfully curated amenities, including a sparkling lakeside pool perfect for unwinding under the sun, a state-of-the-art fitness center for maintaining wellness routines, and a renovated clubhouse ideal for hosting intimate gatherings or quiet evenings with neighbors. Secure key-required lobby access ensures peace of mind, while the meticulously landscaped grounds provide tranquil pathways for leisurely strolls amid lush greenery. Boating enthusiasts will delight in the rentable boat docks and private slips, granting effortless access to the shimmering waters of the lake for leisurely cruises or sunset views. Beyond the grounds, the location places upscale boutiques, fine dining, and cultural vibrancy of Park Avenue just steps away, blending secluded sophistication with the lively pulse of Winter Park. Alabama Condominiums is a condo community in Winter Park, Florida, built between 1921 and 1981. It currently has 1 condo for sale with a list price of $2,490,000. The homes range in size from 993 ft2 to 2,709 ft2. The HOA fees range from $975 to $1,950 per month. The average annual property tax for Alabama Condominiums is $7,949.74. It is located in Orange County.
Albert Lee Ridge Albert Lee Ridge is a single-family home community in Winter Park, Florida, built between 1955 and 1959. It currently has 4 single family homes for sale with an average list price of $422,225. The homes range in size from 1,079 ft2 to 1,974 ft2. The HOA fees range from $1 to $1 per month. The average annual property tax for Albert Lee Ridge is $2,792.02. It is located in Orange County.	Median Price: $405,000
Allison Oakes Allison Oakes is a single-family home community in Winter Park, Florida, built between 1989 and 1993. It currently has no homes for sale. The homes range in size from 916 ft2 to 1,180 ft2. The average annual property tax for Allison Oakes is $1,969.72. It is located in Orange County.	Median Price: $319,500
Aloma Aloma is a single-family home and townhouse community in Winter Park, Florida, built between 1948 and 2021. It currently has 1 lot for sale with a list price of $995,000. The homes range in size from 897 ft2 to 2,855 ft2. The HOA fees range from $207 to $350 per month. The average annual property tax for Aloma is $3,593.61. It is located in Orange County.	Median Price: $485,000
Aloma Park Nestled just minutes from downtown Winter Park, this community provides easy access to shopping, dining, and top-rated schools, while maintaining a tranquil atmosphere. Residents enjoy a range of amenities designed to enhance their lifestyle, including a sparkling swimming pool, a modern fitness center, and well-maintained picnic and barbecue areas. With its prime location near the Cady Way Trail and Lynx bus line, Estates at Aloma Park is perfect for those seeking a peaceful retreat with urban conveniences. Aloma Park is a single-family home community in Winter Park, Florida, built between 1985 and 1990. It currently has no homes for sale. The homes range in size from 1,022 ft2 to 1,058 ft2. The HOA fees range from $48 to $61 per month. The average annual property tax for Aloma Park is $1,941.07. It is located in Seminole County.
Aloma Trails Aloma Trails is a serene gated townhome community offering residents a peaceful retreat with convenient access to the vibrant energy of downtown Orlando. This modern enclave emphasizes effortless living through its secure entry system, which provides a sense of exclusivity and safety, while paver driveways and stone exteriors lend an elegant curb appeal. Aloma Trails is a townhouse community in Winter Park, Florida, built between 2016 and 2018. It currently has 1 townhouse for sale with a list price of $359,500. The homes range in size from 1,787 ft2 to 1,900 ft2. The HOA fees range from $200 to $396 per month. The average annual property tax for Aloma Trails is $3,258.12.	Median Price: $370,000
Amberwood Amberwood is a single-family home community in Winter Park, Florida, built between 1983 and 1987. It currently has no homes for sale. The homes range in size from 1,513 ft2 to 3,116 ft2. The HOA fees range from $18 to $24 per month. The average annual property tax for Amberwood is $3,017.83. It is located in Seminole County.	Median Price: $225,000
Annebury Annebury is a single-family home community in Winter Park, Florida, built in 2005. It currently has no homes for sale. The homes range in size from 2,636 ft2 to 3,285 ft2. The HOA fees range from $110 to $135 per month. The average annual property tax for Annebury is $5,709.10. It is located in Seminole County.	Median Price: $710,000
Aragon Condominiums ragon Condominiums offers an intimate retreat with its two-story buildings encircling a serene central courtyard, providing residents with a peaceful escape just steps from the vibrant downtown scene and a short drive to Orlando's bustling attractions. This welcoming community emphasizes convenience and leisure, boasting a sparkling swimming pool perfect for sunny afternoons, a dedicated laundry room for everyday ease, and a secure bicycle room to encourage eco-friendly exploration of the scenic surroundings. Assigned parking spots and ample guest spaces ensure hassle-free arrivals, while on-site garbage collection and the pool's screened enclosure add to the low-maintenance, resort-like lifestyle that makes Aragon a delightful choice for those seeking sophisticated yet relaxed Florida living. Aragon Condominiums is a condo community in Winter Park, Florida, built in 1984. It currently has 1 condo for sale with a list price of $239,000. The homes have an average size of 808 ft2. The HOA fees range from $260 to $290 per month. The average annual property tax for Aragon Condominiums is $1,353.92. It is located in Orange County.	Median Price: $194,500
Arrowhead Cove Arrowhead Cove is a single-family home community in Winter Park, Florida, built between 1971 and 1974. It currently has no homes for sale. The homes range in size from 1,768 ft2 to 2,616 ft2. The HOA fees range from $8 to $8 per month. The average annual property tax for Arrowhead Cove is $3,721.94. It is located in Orange County.	Median Price: $510,000
Autumn Glen Autumn Glen stands as a serene residential enclave that blends suburban tranquility with urban accessibility. This welcoming community offers an array of modern conveniences designed for effortless living, including a refreshing swimming pool perfect for leisurely laps or sunny gatherings, a well-equipped fitness center to keep wellness routines on track, and lighted tennis courts for spirited matches under the stars. Residents also enjoy the playful energy of a dedicated dog park, the utility of EV charging stations for eco-conscious drivers, and secure on-site storage units for seasonal gear. Gated entry and controlled access provide peace of mind, while a playground invites family fun and a business center supports remote work needs. With its tree-lined streets and proximity to local parks, shops, and dining, Autumn Glen embodies the charm of Central Florida living at its finest. Autumn Glen is a single-family home community in Winter Park, Florida, built between 1967 and 1994. It currently has 1 single family home for sale with a list price of $500,000. The homes range in size from 1,192 ft2 to 2,075 ft2. The HOA fees range from $25 to $137 per month. The average annual property tax for Autumn Glen is $2,876.79. It is located in Seminole County.	Median Price: $409,950
Bear Gully Bay Bear Gully Bay is a single-family home community in Winter Park, Florida, built between 1987 and 1989. It currently has no homes for sale. The homes range in size from 2,170 ft2 to 3,613 ft2. The HOA fees range from $33 to $38 per month. The average annual property tax for Bear Gully Bay is $5,187.56. It is located in Seminole County.	Median Price: $787,500
Bear Gully Forest Bear Gully Forest is a single-family home community in Winter Park, Florida, built in 2003. It currently has no homes for sale. The homes range in size from 1,307 ft2 to 2,336 ft2. The HOA fees range from $44 to $246 per month. The average annual property tax for Bear Gully Forest is $2,701.88. It is located in Seminole County.	Median Price: $535,000
Bear Gully Pointe Bear Gully Pointe is a single-family home community in Winter Park, Florida, built between 1991 and 1995. It currently has no homes for sale. The homes range in size from 3,321 ft2 to 7,895 ft2. The HOA fees range from $133 to $167 per month. The average annual property tax for Bear Gully Pointe is $8,660.92. It is located in Seminole County.	Median Price: $1,080,000
Bel Aire Pines Bel Aire Pines is a single-family home community in Winter Park, Florida, built between 1980 and 1984. It currently has 3 single family homes for sale with an average list price of $461,000. The homes range in size from 1,214 ft2 to 2,878 ft2. The HOA fees range from $3 to $3 per month. The average annual property tax for Bel Aire Pines is $2,783.16. It is located in Orange County.	Median Price: $390,000
Bengert Bend Bengert Bend is a single-family home community in Winter Park, Florida, built between 2005 and 2016. It currently has no homes for sale. The homes range in size from 4,136 ft2 to 4,652 ft2. The average annual property tax for Bengert Bend is $22,222.50. It is located in Orange County.
Bennington Bennington is a single-family home community in Winter Park, Florida, built between 2002 and 2003. It currently has no homes for sale. The homes range in size from 1,626 ft2 to 2,453 ft2. The HOA fees range from $35 to $35 per month. The average annual property tax for Bennington is $2,790. It is located in Seminole County.	Median Price: $455,000
Bridgewater Bridgewater is a single-family home community in Winter Park, Florida, built between 1988 and 1990. It currently has 1 single family home for sale with a list price of $424,900. The homes range in size from 1,298 ft2 to 1,685 ft2. The HOA fees range from $220 to $230 per month. The average annual property tax for Bridgewater is $2,720.00. It is located in Seminole County.	Median Price: $392,000
Brookshire Heights Brookshire Heights is a charming residential neighborhood celebrated for its serene, tree-lined streets and family-friendly vibe, where neighbors bond over shared passions for gardening, dog walking, and community events. Residents enjoy easy access to top-rated schools, nearby parks like Ward Park with its sports fields, pool, and scenic wetlands trails, as well as the expansive Winter Park/Cady Way Bike Trail for leisurely rides. The area's walkable paths lead to the vibrant Downtown Winter Park, brimming with sidewalk cafes, eclectic shops, farmers' markets, festivals, and cultural museums, while convenient proximity to shopping centers, dining options, and major highways like I-4 ensures effortless exploration of greater Orlando. Brookshire Heights is a single-family home community in Winter Park, Florida, built between 1958 and 2025. It currently has 4 single family homes for sale with an average list price of $566,000. The homes range in size from 989 ft2 to 3,854 ft2. The average annual property tax for Brookshire Heights is $4,518.37. It is located in Orange County.	Median Price: $593,000
Bungalow Park Bungalow Park is a single-family home community in Winter Park, Florida, built between 1920 and 2021. It currently has no homes for sale. The homes range in size from 1,049 ft2 to 2,472 ft2. The average annual property tax for Bungalow Park is $3,119.66. It is located in Orange County.	Median Price: $467,500
Campo Bello Campo Bello is a serene residential subdivision celebrated for its picturesque, tree-lined brick streets and proximity to vibrant local hotspots. Residents relish a low-maintenance lifestyle with easy access to nearby dining options, grocery stores, and Winter Park Hospital, all just a short stroll or drive away. It's prime location affords effortless enjoyment of surrounding amenities like the nearby YMCA for fitness and recreational pursuits, as well as the scenic allure of nearby lakes and parks that invite outdoor relaxation and community events. This idyllic enclave perfectly blends historic charm with modern convenience, making it a coveted gem in Central Florida's cultural landscape. Campo Bello is a single-family home community in Winter Park, Florida, built between 1950 and 2017. It currently has 1 lot for sale with a list price of $3,960,000. The homes range in size from 1,436 ft2 to 4,242 ft2. The average annual property tax for Campo Bello is $10,401.57. It is located in Orange County.
Camwood Camwood is a single-family home community in Winter Park, Florida, built between 1950 and 2025. It currently has 2 single family homes for sale with an average list price of $4,100,000. The homes range in size from 3,772 ft2 to 6,981 ft2. The average annual property tax for Camwood is $20,124.34. It is located in Orange County.	Median Price: $6,300,000
Carolyn Estates Carolyn Estates is a single-family home community in Winter Park, Florida, built between 1979 and 1984. It currently has 1 single family home for sale with a list price of $525,000. The homes range in size from 1,550 ft2 to 2,062 ft2. The HOA fees range from $8 to $9 per month. The average annual property tax for Carolyn Estates is $2,477.68. It is located in Seminole County.	Median Price: $475,000
Carver Town Carver Town is a single-family home community in Winter Park, Florida, built between 1948 and 2019. It currently has 2 single family homes for sale with an average list price of $512,500. The homes range in size from 754 ft2 to 2,232 ft2. The average annual property tax for Carver Town is $3,314.18. It is located in Orange County.	Median Price: $637,500
Casa Aloma Casa Aloma is a single-family home community in Winter Park, Florida, built between 1968 and 1970. It currently has 4 single family homes for sale with an average list price of $480,175. The homes range in size from 1,627 ft2 to 2,247 ft2. The HOA fees range from $2 to $2 per month. The average annual property tax for Casa Aloma is $2,604.82. It is located in Seminole County.	Median Price: $420,000
Casa Jardin Casa Jardin embodies the charm of Santa Barbara-style elegance, offering an exclusive enclave of townhomes that blend serene privacy with effortless sophistication. Residents relish a lock-and-leave lifestyle enhanced by private driveways and tree-top terraces, ideal for quiet reflection or al fresco entertaining, while a secluded hideaway room provides versatile space for exercise, media viewing, or a dedicated office retreat. The community thrives on its proximity to vibrant local gems, all within easy walking distance, including the upscale boutiques and dining along Park Avenue, the lush expanses of Mead Botanical Garden for nature escapes, the recreational courts at Winter Park Tennis Center, the family-friendly Azalea Park playground, and direct access to Lake Virginia for kayaking and paddleboarding adventures. This gated oasis fosters a sense of refined tranquility, where manicured gardens and thoughtful design invite leisurely days amid Winter Park's timeless allure. Casa Jardin is a condo and townhouse community in Winter Park, Florida, built between 2004 and 2007. It currently has 1 condo for sale with a list price of $769,000. The homes have an average size of 1,957 ft2. The HOA fees range from $586 to $717 per month. The average annual property tax for Casa Jardin is $7,473.12.	Median Price: $792,500
Cedar Ridge Cedar Ridge is a single-family home community in Winter Park, Florida, built between 1979 and 1983. It currently has no homes for sale. The homes range in size from 1,120 ft2 to 2,044 ft2. The average annual property tax for Cedar Ridge is $2,556.54. It is located in Seminole County.	Median Price: $380,000
Cedarwood Village Cedarwood Village stands as a serene and upscale condominium community, renowned for its lush landscapes and inviting atmosphere that fosters a sense of community and relaxation. Residents cherish the vibrant social scene centered around the on-site clubhouse, where gatherings and events bring neighbors together effortlessly. The community pool offers a refreshing oasis for leisurely swims and sunbathing amid tropical surroundings, while the tennis and basketball courts provide ample opportunities for active pursuits and friendly competitions. Additional conveniences like wheelchair accessibility, recreation facilities, and even golf cart-friendly paths enhance daily living, making Cedarwood Village an ideal haven for those seeking a blend of leisure, convenience, and Florida's renowned outdoor lifestyle. Cedarwood Village is a condo and townhouse community in Winter Park, Florida, built between 1980 and 1987. It currently has 5 condos for sale with an average list price of $299,080. The homes range in size from 1,173 ft2 to 1,669 ft2. The HOA fees range from $312 to $511 per month. The average annual property tax for Cedarwood Village is $2,028.44. It is located in Seminole County.	Median Price: $242,500
Charmont Charmont is a single-family home community in Winter Park, Florida, built between 1935 and 2026. It currently has 2 single family homes for sale with an average list price of $2,325,250. The homes range in size from 1,118 ft2 to 5,782 ft2. The average annual property tax for Charmont is $9,563.19. It is located in Orange County.	Median Price: $1,235,739
Chateaux Du Lac Nestled along the serene shores of Lake Killarney, Chateaux Du Lac is a charming condominium community that embodies relaxed lakeside elegance. Residents delight in an array of thoughtful amenities designed to enhance everyday living, including a heated swimming pool perfect for leisurely laps or sun-soaked afternoons, a private boat dock and ramp for effortless access to the skiable waters of the lake, and a welcoming clubhouse ideal for gatherings and relaxation. On-site laundry facilities add convenience to the mix, while the community deck offers stunning sunset views that capture the magic of Florida's waterfront lifestyle. Just steps from the vibrant Winter Park Village, this enclave fosters a sense of community through regular resident events, blending tranquility with easy proximity to shopping, dining, and cultural pursuits. Chateaux Du Lac is a condo community in Winter Park, Florida, built in 1972. It currently has 3 condos for sale with an average list price of $240,833.33. The homes range in size from 732 ft2 to 1,026 ft2. The HOA fees range from $229 to $405 per month. The average annual property tax for Chateaux Du Lac is $2,133.87. It is located in Orange County.	Median Price: $248,000
Cinnamon Shores Cinnamon Shores is a single-family home community in Winter Park, Florida, built between 1981 and 1990. It currently has no homes for sale. The homes range in size from 2,424 ft2 to 3,472 ft2. The average annual property tax for Cinnamon Shores is $7,227. It is located in Orange County.
Citrus Point Citrus Point is a single-family home community in Winter Park, Florida, built between 1985 and 1987. It currently has no homes for sale. The homes range in size from 1,407 ft2 to 2,043 ft2. The HOA fees range from $125 to $125 per month. The average annual property tax for Citrus Point is $2,044.50. It is located in Seminole County.
Cloister Grove Cloister Grove is a single-family home community in Winter Park, Florida, built between 1919 and 2026. It currently has 1 single family home for sale with a list price of $4,750,000. The homes range in size from 2,505 ft2 to 10,734 ft2. The average annual property tax for Cloister Grove is $23,958.44. It is located in Orange County.	Median Price: $1,875,000
Colonies The Colonies condominium community offers residents a serene yet convenient lifestyle amid lush, beautifully landscaped grounds and thoughtfully designed common areas. Key amenities include a refreshing swimming pool for leisurely swims, a welcoming clubhouse for social gatherings and events, a dedicated dog park for pet owners to let their furry companions play, and tennis courts for active pursuits and friendly matches. Beyond the community's own offerings, proximity to nearby parks invites outdoor exploration and relaxation, while top-rated schools, diverse shopping centers, and an array of dining options ensure everyday essentials and entertainment are just moments away. With easy access to major highways and cultural hotspots like downtown Winter Park's scenic lakes and gardens, The Colonies blends tranquil living with the energy of a dynamic neighborhood, fostering a strong sense of community for families, professionals, and retirees alike. Colonies is a condo community in Winter Park, Florida, built in 1974. It currently has 14 condos for sale with an average list price of $108,971.36. The homes range in size from 525 ft2 to 1,356 ft2. The HOA fees range from $139 to $599 per month. The average annual property tax for Colonies is $1,126.79. It is located in Orange County.	Median Price: $96,000
Comstock Park Comstock Park exudes timeless charm with its tree-lined streets and easy access to the city's vibrant cultural scene. Residents enjoy a wealth of amenities right at their doorstep, including proximity to the lush Martin Luther King Jr. Park for leisurely strolls and outdoor recreation, as well as the nearby Winter Park Community Center for fitness classes and events. The neighborhood's prime location offers convenient walks to Park Avenue's upscale boutiques, acclaimed restaurants, and art galleries, while the adjacent Winter Park Village provides modern shopping hubs like Publix and Whole Foods. Additional perks include seamless connectivity to SunRail for effortless commuting, Rollins College's scenic campus, and a short drive to major highways, downtown Orlando attractions, and pristine beaches, blending serene suburban living with urban sophistication. Comstock Park is a single-family home community in Winter Park, Florida, built between 1946 and 2025. It currently has 2 single family homes for sale with an average list price of $3,324,999.50. The homes range in size from 1,446 ft2 to 6,406 ft2. The average annual property tax for Comstock Park is $11,301.70. It is located in Orange County.	Median Price: $1,075,000
Conwill Estates Conwill Estates is a single-family home community in Winter Park, Florida, built between 1954 and 2025. It currently has 3 single family homes for sale with an average list price of $2,090,000. The homes range in size from 1,387 ft2 to 4,425 ft2. The average annual property tax for Conwill Estates is $7,324.36. It is located in Orange County.	Median Price: $1,040,000
Coronation Coronation is a single-family home community in Winter Park, Florida, built between 1982 and 1983. It currently has no homes for sale. The homes range in size from 1,030 ft2 to 1,365 ft2. The average annual property tax for Coronation is $1,787.63. It is located in Orange County.	Median Price: $230,000
Cortland Park Cortland Park is a single-family home community in Winter Park, Florida, built between 1925 and 2012. It currently has 2 single family homes for sale with an average list price of $937,500. The homes range in size from 1,683 ft2 to 4,168 ft2. The average annual property tax for Cortland Park is $9,876.09. It is located in Orange County.	Median Price: $2,100,000
Country Lane Country Lane offers residents a serene, lakefront lifestyle nestled along the shores of Lake Florence, where lush greenery and quiet streets create an inviting suburban retreat just minutes from the vibrant heart of Winter Park. This close-knit community features a range of thoughtful amenities, including well-maintained tennis courts for active pursuits, scenic walking paths that wind through the neighborhood, and access to private lakefront spots ideal for boating or simply unwinding by the water. Beyond the immediate surroundings, Country Lane's prime location provides effortless connectivity to Winter Park's upscale offerings, such as the tree-lined Park Avenue district with its boutique shops, award-winning restaurants, and cultural gems like the Orlando Museum of Art, all while embracing the area's renowned parks, golf courses, and year-round community events that foster a sense of belonging and leisure. Country Lane is a single-family home community in Winter Park, Florida, built between 1984 and 1986. It currently has 2 single family homes for sale with an average list price of $367,699.50. The homes range in size from 1,118 ft2 to 2,035 ft2. The HOA fees range from $39 to $50 per month. The average annual property tax for Country Lane is $2,668.47. It is located in Seminole County.	Median Price: $450,000
Cranes Creek Cranes Creek is a townhouse and condo community in Winter Park, Florida, built between 2006 and 2007. It currently has no homes for sale. The homes range in size from 1,471 ft2 to 1,610 ft2. The HOA fees range from $142 to $142 per month. The average annual property tax for Cranes Creek is $2,658.33. It is located in Orange County.
Cypress Reserve Nestled in the serene Bear Gully Lake, Cypress Reserve stands out as an exclusive gated community that blends natural tranquility with upscale suburban living. Residents enjoy a host of thoughtful amenities designed to foster relaxation and connection, including a resort-style swimming pool and cabana for leisurely swims and social gatherings, a dedicated playground and tot lots perfect for family playtime, and scenic walking paths lined with conservation land and benches that invite daily strolls amid lush woodlands. The neighborhood's walkable layout, enhanced by its dog-friendly vibe and proximity to nearby parks, promotes an active lifestyle while maintaining a peaceful, family-oriented atmosphere just minutes from downtown Winter Park's vibrant shops, restaurants, and schools. Cypress Reserve is a single-family home community in Winter Park, Florida, built between 1997 and 1999. It currently has 1 single family home for sale with a list price of $918,000. The homes range in size from 2,433 ft2 to 3,983 ft2. The HOA fees range from $100 to $140 per month. The average annual property tax for Cypress Reserve is $5,539.52. It is located in Seminole County.	Median Price: $1,165,000
Dixie Terrace Dixie Terrace is a single-family home community in Winter Park, Florida, built between 1927 and 2024. It currently has 4 single family homes for sale with an average list price of $1,492,498. The homes range in size from 830 ft2 to 4,211 ft2. The average annual property tax for Dixie Terrace is $6,536.44. It is located in Orange County.	Median Price: $1,045,000
Dommerich Cove Dommerich Cove is a serene residential enclave offering residents a tranquil lakeside lifestyle amid lush conservation areas and mature tree-lined streets. This family-friendly community stands out for its exceptional educational amenities, with homes within easy walking distance of the highly regarded Dommerich Elementary School, providing a safe and convenient environment for young families. Proximity to Maitland Middle and Winter Park High schools further enhances its appeal for those prioritizing top-tier public education. Outdoor enthusiasts appreciate the nearby park facilities, which include tennis and basketball courts, picnic pavilions equipped with grills, and dedicated playsets for children, fostering a vibrant sense of community and recreation. The neighborhood's location grants effortless access to Winter Park's cultural gems, such as the renowned public library, upscale dining options, and the Orlando Museum of Art, blending suburban peace with urban sophistication. Dommerich Cove is a single-family home community in Winter Park, Florida, built between 1964 and 1965. It currently has no homes for sale. The homes range in size from 2,458 ft2 to 3,377 ft2. The average annual property tax for Dommerich Cove is $4,611.05. It is located in Orange County.	Median Price: $1,050,000
Dommerich Forest Dommerich Forest is a single-family home community in Winter Park, Florida, built in 1973. It currently has no homes for sale. The homes range in size from 1,680 ft2 to 2,239 ft2. The average annual property tax for Dommerich Forest is $4,053.89. It is located in Orange County.
Dommerich Hills Dommerich Hills is a single-family home community in Winter Park, Florida, built between 1965 and 1969. It currently has no homes for sale. The homes range in size from 1,894 ft2 to 4,364 ft2. The average annual property tax for Dommerich Hills is $5,230.72. It is located in Orange County.	Median Price: $534,590
Dubsdread Heights Dubsdread Heights is a single-family home community in Winter Park, Florida, built between 1925 and 2020. It currently has 3 single family homes for sale with an average list price of $708,300. The homes range in size from 704 ft2 to 6,700 ft2. The average annual property tax for Dubsdread Heights is $4,395.24. It is located in Orange County.	Median Price: $380,000
Eastbrook Eastbrook is a single-family home community in Winter Park, Florida, built between 1958 and 2023. It currently has 16 single family homes for sale with an average list price of $416,268.13. The homes range in size from 989 ft2 to 4,266 ft2. The HOA fees range from $2 to $364 per month. The average annual property tax for Eastbrook is $2,365.76. It is located in Seminole County.	Median Price: $380,000
Eastgate Eastgate is a single-family home community in Winter Park, Florida, built between 1955 and 2025. It currently has 3 single family homes for sale with an average list price of $783,000. The homes range in size from 1,322 ft2 to 2,718 ft2. The average annual property tax for Eastgate is $3,386.60. It is located in Orange County.	Median Price: $412,500
Eden Point Eden Point is a single-family home community in Winter Park, Florida, built between 2014 and 2015. It currently has no homes for sale. The homes range in size from 2,654 ft2 to 4,088 ft2. The HOA fees range from $120 to $127 per month. The average annual property tax for Eden Point is $6,489.80. It is located in Seminole County.	Median Price: $910,000
Ellno Willo Ellno Willo is a single-family home community in Winter Park, Florida, built between 1925 and 2021. It currently has no homes for sale. The homes range in size from 1,912 ft2 to 8,188 ft2. The average annual property tax for Ellno Willo is $18,158.30. It is located in Orange County.	Median Price: $1,250,000
Enclave at Aloma Enclave at Aloma is a single-family home community in Winter Park, Florida, built between 2013 and 2016. It currently has 2 single family homes for sale with an average list price of $625,000. The homes range in size from 1,843 ft2 to 3,568 ft2. The HOA fees range from $83 to $144 per month. The average annual property tax for Enclave at Aloma is $4,762.04. It is located in Seminole County.	Median Price: $625,000
Ethel Park Ethel Park is a single-family home community in Winter Park, Florida, built between 1949 and 2006. It currently has no homes for sale. The homes range in size from 1,270 ft2 to 4,587 ft2. The average annual property tax for Ethel Park is $8,564.44. It is located in Orange County.
Fairbanks Park Fairbanks Park is a single-family home and townhouse community in Winter Park, Florida, built between 1925 and 2021. It currently has no homes for sale. The homes range in size from 960 ft2 to 3,186 ft2. The HOA fees range from $200 to $217 per month. The average annual property tax for Fairbanks Park is $5,827.26. It is located in Orange County.	Median Price: $925,000
Fairbanks Shores Fairbanks Shores is a single-family home community in Winter Park, Florida, built between 1953 and 2023. It currently has 1 single family home for sale with a list price of $402,000. The homes range in size from 1,030 ft2 to 1,925 ft2. The average annual property tax for Fairbanks Shores is $1,702.03. It is located in Orange County.	Median Price: $454,000
Fernbrook Trails Fernbrook Trails is a townhouse community in Winter Park, Florida, built between 1984 and 1985. It currently has no homes for sale. The homes range in size from 1,092 ft2 to 1,499 ft2. The HOA fees range from $55 to $99 per month. The average annual property tax for Fernbrook Trails is $2,367.74. It is located in Seminole County.	Median Price: $266,000
Flora Park Flora Park is a single-family home community in Winter Park, Florida, built between 1957 and 2017. It currently has 1 single family home for sale with a list price of $1,995,000. The homes range in size from 1,906 ft2 to 3,897 ft2. The average annual property tax for Flora Park is $9,115.65. It is located in Orange County.	Median Price: $2,120,000
Fontainebleau The Fontainebleau neighborhood exudes timeless elegance amid a lush canopy of mature trees and tropical landscapes, offering residents a serene retreat just moments from the vibrant energy of Park Avenue's charming brick-lined streets, alfresco cafes, boutiques, museums, and scenic Central Park. This exclusive enclave provides easy access to the picturesque Winter Park Chain of Lakes for boating enthusiasts, top-rated schools including Winter Park High with its acclaimed International Baccalaureate program, and convenient proximity to downtown Orlando's business hubs, medical facilities, and major highways for effortless commuting. Fontainebleau is a single-family home community in Winter Park, Florida, built between 1956 and 2024. It currently has 1 single family home for sale with a list price of $1,775,000. The homes range in size from 1,442 ft2 to 5,263 ft2. The average annual property tax for Fontainebleau is $12,563.08. It is located in Orange County.	Median Price: $2,175,000
Forrest Hills Forrest Hills is a single-family home community in Winter Park, Florida, built between 1947 and 2025. It currently has 5 single family homes for sale with an average list price of $3,200,980. The homes range in size from 1,568 ft2 to 5,936 ft2. The average annual property tax for Forrest Hills is $12,412.84. It is located in Orange County.	Median Price: $3,072,500
Four Seasons The Four Seasons condominium community offers a serene and vibrant retreat for residents seeking a blend of relaxation and recreation. This established enclave features three inviting swimming pools perfect for leisurely laps or sunny afternoons, a regulation tennis court for friendly matches, and shuffleboard courts that encourage casual gatherings among neighbors. At the heart of the community lies a welcoming clubhouse equipped with a cozy library, ideal for quiet reading or social events, alongside convenient laundry facilities to simplify daily life. Gated for added security, the grounds include controlled access, ample storage units, and a playground for little ones, while pet owners will appreciate the dedicated dog park and EV charging stations for eco-friendly convenience. With its thoughtful amenities fostering a strong sense of community, Four Seasons provides an idyllic backdrop for enjoying the laid-back elegance of Central Florida living. Four Seasons is a condo community in Winter Park, Florida, built in 1970. It currently has 3 condos for sale with an average list price of $222,966.67. The homes range in size from 727 ft2 to 1,322 ft2. The HOA fees range from $100 to $480 per month. The average annual property tax for Four Seasons is $1,614.07. It is located in Orange County.	Median Price: $170,000
Fremar Fremar is a single-family home community in Winter Park, Florida, built between 1955 and 2023. It currently has no homes for sale. The homes range in size from 1,332 ft2 to 4,435 ft2. The average annual property tax for Fremar is $9,807.57. It is located in Orange County.
Gallery at Winter Park The Gallery at Winter Park condominium community offers residents a tranquil retreat just minutes from the vibrant energy of downtown Orlando. This inviting enclave embodies effortless sophistication, where mature oaks and lush greenery frame elegant residences designed for modern comfort. Residents revel in a host of thoughtful amenities that elevate everyday living, including a sparkling community pool perfect for leisurely laps or sunny afternoons, lighted tennis courts for spirited matches under the stars, a cozy clubhouse ideal for gatherings and relaxation, and convenient storage facilities along with an indoor bike room to keep active pursuits organized. With its central location near renowned cultural spots, scenic trails like the Cady Way, and top-rated wellness centers, the Gallery at Winter Park seamlessly blends quiet luxury with the charm of lakeside living, inviting you to unwind in style. Gallery at Winter Park is a condo community in Winter Park, Florida, built between 1984 and 1985. It currently has 1 condo for sale with a list price of $298,000. The homes range in size from 893 ft2 to 1,026 ft2. The HOA fees range from $437 to $647 per month. The average annual property tax for Gallery at Winter Park is $1,716.89. It is located in Orange County.	Median Price: $290,000
Galloway Place Galloway Place is a single-family home community in Winter Park, Florida, built between 1928 and 2023. It currently has 1 single family home for sale with a list price of $665,000. The homes range in size from 1,804 ft2 to 3,738 ft2. The average annual property tax for Galloway Place is $13,723.38. It is located in Orange County.	Median Price: $3,237,500
Garden Grove Garden Grove is a single-family home community in Winter Park, Florida, built between 1985 and 1988. It currently has 1 single family home for sale with a list price of $409,999. The homes range in size from 1,120 ft2 to 1,786 ft2. The HOA fees range from $13 to $13 per month. The average annual property tax for Garden Grove is $2,532.68. It is located in Seminole County.	Median Price: $340,000
Garden Lake Estates Garden Lake Estates is a single-family home community in Winter Park, Florida, built between 1978 and 1984. It currently has 3 single family homes for sale with an average list price of $436,133.33. The homes range in size from 1,525 ft2 to 2,124 ft2. The HOA fees range from $2 to $2 per month. The average annual property tax for Garden Lake Estates is $2,648.38. It is located in Seminole County.	Median Price: $476,500
Georgetown Estates Georgetown Estates embodies the essence of suburban serenity with its well-maintained homes, lush greenery, and tree-lined streets that foster a strong sense of community. This peaceful, family-friendly enclave offers residents a quiet retreat ideal for both young families and retirees, enhanced by its proximity to top-rated schools and essential local conveniences like parks, shopping districts, and dining options. The neighborhood's welcoming vibe is evident in its high friendliness rating, where neighbors often connect over shared walks or casual gatherings, while easy access to major highways ensures effortless commutes to downtown Orlando and nearby theme parks, blending everyday tranquility with the excitement of Central Florida living. Georgetown Estates is a single-family home community in Winter Park, Florida, built between 1965 and 1995. It currently has 1 single family home for sale with a list price of $390,000. The homes range in size from 1,200 ft2 to 2,301 ft2. The average annual property tax for Georgetown Estates is $2,654.77. It is located in Orange County.	Median Price: $379,900
Glenmoor Glenmoor is a single-family home community in Winter Park, Florida, built between 1983 and 2021. It currently has 1 single family home for sale with a list price of $389,900. The homes range in size from 1,217 ft2 to 2,288 ft2. The average annual property tax for Glenmoor is $2,976.69. It is located in Orange County.	Median Price: $415,000
Goldenrod Place Goldenrod Place is a single-family home community in Winter Park, Florida, built between 1972 and 1973. It currently has no homes for sale. The homes range in size from 1,350 ft2 to 1,467 ft2. The average annual property tax for Goldenrod Place is $1,951.90. It is located in Seminole County.	Median Price: $400,000
Goldenrod Villas Situated just minutes from major hubs like Full Sail University, UCF, and Park Avenue’s vibrant shops and dining, this community combines suburban tranquility with urban convenience. Residents enjoy a range of amenities, including a refreshing community pool, tennis courts, and a clubhouse perfect for social gatherings. Goldenrod Villas is a condo community in Winter Park, Florida, built between 1982 and 1988. It currently has 2 condos for sale with an average list price of $252,450. The homes range in size from 1,068 ft2 to 1,230 ft2. The HOA fees range from $231 to $308 per month. The average annual property tax for Goldenrod Villas is $1,690.91. It is located in Seminole County.	Median Price: $260,000
Golfside Golfside is a single-family home community in Winter Park, Florida, built between 1967 and 1979. It currently has 1 single family home for sale with a list price of $499,900. The homes range in size from 1,286 ft2 to 2,630 ft2. The average annual property tax for Golfside is $5,012.24. It is located in Orange County.	Median Price: $730,000
Golfside Villas Golfside Villas offers a serene condominium community that seamlessly blends suburban tranquility with urban convenience, just moments from the renowned Winter Park Golf Course and a short drive to downtown Orlando. Residents relish a host of inviting amenities designed for leisure and an active lifestyle, including a sparkling community pool perfect for cooling off on sunny afternoons, tennis courts for friendly matches, and a playful playground for families. Thoughtful outdoor features abound, such as well-maintained walking paths winding through beautifully landscaped gardens, private patios and balconies for al fresco relaxation, and assigned parking for effortless arrivals. Golfside Villas is a condo community in Winter Park, Florida, built in 1969. It currently has 6 condos for sale with an average list price of $186,316.50. The homes range in size from 735 ft2 to 1,554 ft2. The HOA fees range from $220 to $350 per month. The average annual property tax for Golfside Villas is $1,222.63. It is located in Orange County.	Median Price: $140,000
Golfview Golfview is a single-family home community in Winter Park, Florida, built between 1926 and 2024. It currently has 2 single family homes for sale with an average list price of $624,495. The homes range in size from 864 ft2 to 4,196 ft2. The average annual property tax for Golfview is $4,122.07. It is located in Orange County.	Median Price: $572,500
Golfview Heights Golfview Heights is a single-family home community in Winter Park, Florida, built between 1953 and 2025. It currently has 1 single family home for sale with a list price of $1,199,900. The homes range in size from 1,488 ft2 to 4,812 ft2. The average annual property tax for Golfview Heights is $9,901.28. It is located in Orange County.	Median Price: $2,309,000
Golfview Terrace Golfview Terrace is a single-family home community in Winter Park, Florida, built between 1918 and 2023. It currently has no homes for sale. The homes range in size from 4,617 ft2 to 5,406 ft2. The average annual property tax for Golfview Terrace is $18,191.20. It is located in Orange County.
Grand Pines Grand Pines is a single-family home community in Winter Park, Florida, built between 1982 and 1985. It currently has no homes for sale. The homes range in size from 968 ft2 to 1,439 ft2. The average annual property tax for Grand Pines is $1,566.90. It is located in Seminole County.
Grayson Square Grayson Square is a townhouse community in Winter Park, Florida, built between 2022 and 2024 by Pulte Homes. It currently has 4 townhouses for sale with an average list price of $443,225. The homes range in size from 1,782 ft2 to 1,916 ft2. The HOA fees range from $275 to $375 per month. The average annual property tax for Grayson Square is $917.47. It is located in Seminole County.	Median Price: $423,000
Green Oaks Green Oaks is a single-family home community in Winter Park, Florida, built between 1957 and 2024. It currently has 2 single family homes for sale with an average list price of $4,537,499.50. The homes range in size from 2,281 ft2 to 8,583 ft2. The HOA fees range from $2 to $2 per month. The average annual property tax for Green Oaks is $15,047.93. It is located in Orange County.	Median Price: $3,450,000
Green Terrace Green Terrace is a single-family home community in Winter Park, Florida, built between 1958 and 2018. It currently has no homes for sale. The homes range in size from 1,345 ft2 to 3,249 ft2. The average annual property tax for Green Terrace is $8,835.51. It is located in Orange County.
Greenview at Winter Pines Greenview at Winter Pines offers residents an idyllic suburban retreat centered around the scenic Winter Pines Golf Club, where lush fairways and serene water features provide endless opportunities for leisurely rounds amid Florida's natural beauty. The community boasts convenient access to everyday essentials like a nearby Publix grocery store and a Walmart just a short drive away, while its prime location ensures effortless proximity to the vibrant charm of Downtown Winter Park's upscale shopping, diverse dining scene, and cultural hotspots. Higher education enthusiasts will appreciate the easy commute to Rollins College, and aviation aficionados can zip over to Orlando Executive Airport for quick getaways. With its tree-lined streets and welcoming neighborhood vibe, Greenview at Winter Pines embodies a perfect blend of relaxation and refined living, inviting homeowners to unwind in a setting that feels both exclusive and effortlessly accessible. Greenview at Winter Pines is a single-family home community in Winter Park, Florida, built between 1978 and 2002. It currently has 2 single family homes for sale with an average list price of $767,500. The homes range in size from 1,689 ft2 to 3,082 ft2. The average annual property tax for Greenview at Winter Pines is $4,479.71.	Median Price: $685,000
Hamilton Place Hamilton Place is a single-family home community in Winter Park, Florida, built between 2007 and 2015. It currently has 1 single family home for sale with a list price of $1,295,000. The homes range in size from 2,810 ft2 to 3,363 ft2. The HOA fees range from $122 to $142 per month. The average annual property tax for Hamilton Place is $7,562.96. It is located in Orange County.	Median Price: $1,125,000
Harbour Ridge Harbour Ridge is a single-family home community in Winter Park, Florida, built between 1982 and 1986. It currently has no homes for sale. The homes range in size from 1,318 ft2 to 2,464 ft2. The HOA fees range from $8 to $8 per month. The average annual property tax for Harbour Ridge is $2,677.36. It is located in Seminole County.	Median Price: $402,500
Hidden Oaks Hidden Oaks is a condo and townhouse community in Winter Park, Florida, built between 1983 and 1984. It currently has 5 townhouses for sale with an average list price of $212,979.60 and 2 condos for sale with an average list price of $199,200. The homes range in size from 990 ft2 to 1,161 ft2. The HOA fees range from $200 to $420 per month. The average annual property tax for Hidden Oaks is $1,548.26. It is located in Orange County.	Median Price: $175,000
Howell Branch Woods Howell Branch Woods is a single-family home community in Winter Park, Florida, built between 1976 and 1978. It currently has 1 single family home for sale with a list price of $399,900. The homes range in size from 1,196 ft2 to 2,144 ft2. The average annual property tax for Howell Branch Woods is $2,602.42. It is located in Seminole County.	Median Price: $432,400
Howell Estates Howell Estates is a single-family home community in Winter Park, Florida, built between 1935 and 1984. It currently has 2 single family homes for sale with an average list price of $427,500. The homes range in size from 1,143 ft2 to 2,762 ft2. The HOA fees range from $2 to $25 per month. The average annual property tax for Howell Estates is $2,674.66.	Median Price: $415,000
Howell Forests Howell Forests is a single-family home community in Winter Park, Florida, built between 1968 and 1969. It currently has 1 single family home for sale with a list price of $749,000. The homes range in size from 1,604 ft2 to 3,538 ft2. The average annual property tax for Howell Forests is $4,438.69. It is located in Orange County.
Huntington Condominiums Huntington Condominiums is a condo community in Winter Park, Florida, built in 1981. It currently has no homes for sale. The homes range in size from 1,204 ft2 to 1,234 ft2. The HOA fees range from $375 to $375 per month. The average annual property tax for Huntington Condominiums is $3,806.11. It is located in Orange County.	Median Price: $330,000
Hyde Park Hyde Park is a single-family home community in Winter Park, Florida, built between 1986 and 1989. It currently has 1 single family home for sale with a list price of $475,000. The homes range in size from 1,408 ft2 to 2,018 ft2. The HOA fees range from $22 to $37 per month. The average annual property tax for Hyde Park is $2,603.77. It is located in Seminole County.	Median Price: $400,000
J Kronenberger J Kronenberger is a single-family home community in Winter Park, Florida, built between 1925 and 2021. It currently has 2 single family homes for sale with an average list price of $3,847,000. The homes range in size from 2,550 ft2 to 10,997 ft2. The average annual property tax for J Kronenberger is $18,874.74. It is located in Orange County.	Median Price: $2,087,500
Jenkins Jenkins is a single-family home community in Winter Park, Florida, built between 1951 and 2020. It currently has no homes for sale. The homes range in size from 1,989 ft2 to 4,579 ft2. The average annual property tax for Jenkins is $9,602.99. It is located in Orange County.	Median Price: $1,409,000
Killarney Bay Condominiums Killarney Bay Condominiums is a condo community in Winter Park, Florida, built in 1986. It currently has 4 condos for sale with an average list price of $423,000. The homes range in size from 1,140 ft2 to 1,718 ft2. The HOA fees range from $238 to $446 per month. The average annual property tax for Killarney Bay Condominiums is $2,810.70. It is located in Orange County.	Median Price: $385,000
Killarney Circle Killarney Circle is a single-family home community in Winter Park, Florida, built between 1951 and 2005. It currently has 2 single family homes for sale with an average list price of $984,500. The homes range in size from 729 ft2 to 3,749 ft2. The average annual property tax for Killarney Circle is $4,928.25. It is located in Orange County.	Median Price: $420,000
Killarney Estates Killarney Estates is a single-family home community in Winter Park, Florida, built between 1925 and 2026. It currently has 2 single family homes for sale with an average list price of $1,390,000. The homes range in size from 840 ft2 to 3,253 ft2. The average annual property tax for Killarney Estates is $3,623.80. It is located in Orange County.	Median Price: $719,500
Killarney Point Killarney Point is a single-family home community in Winter Park, Florida, built between 1953 and 2012. It currently has no homes for sale. The homes range in size from 1,412 ft2 to 6,000 ft2. The average annual property tax for Killarney Point is $12,568.21. It is located in Orange County.	Median Price: $2,555,000
King's Cove King's Cove is a single-family home community in Winter Park, Florida, built between 1988 and 1991. It currently has no homes for sale. The homes range in size from 1,788 ft2 to 2,387 ft2. The HOA fees range from $22 to $26 per month. The average annual property tax for King's Cove is $3,809.20. It is located in Seminole County.	Median Price: $470,000
Lake Bell Terrace Lake Bell Terrace is a serene and welcoming neighborhood celebrated for its tranquil lakeside setting along the private ski lake, Lake Bell, where residents relish stunning water views and easy access to outdoor pursuits like boating and waterskiing. This family-friendly enclave exudes charm and convenience, with tree-lined streets perfect for leisurely walks and a strong sense of community that fosters neighborly connections through local events and gatherings. Amenities abound in this walkable haven, including proximity to beloved dining spots, scenic hiking trails, and lush green spaces ideal for gardening, yoga, and pet-friendly strolls, all while offering a peaceful retreat from the bustle just minutes from vibrant Winter Park hotspots. Lake Bell Terrace is a single-family home community in Winter Park, Florida, built between 1957 and 1959. It currently has 1 single family home for sale with a list price of $835,000. The homes range in size from 1,132 ft2 to 2,237 ft2. The average annual property tax for Lake Bell Terrace is $2,161.38. It is located in Orange County.	Median Price: $439,900
Lake Florence Preserve Lake Florence Preserve is an exclusive, gated waterfront community featuring 28 luxurious single-family homes situated along the serene southern bank of Lake Florence. This prestigious neighborhood offers a tranquil and upscale lifestyle in one of Central Florida’s most sought-after areas, known for its high-end boutiques, renowned restaurants, and top-rated schools. While the community itself has limited amenities, focusing on privacy and natural beauty, residents benefit from proximity to Winter Park’s abundant recreational offerings, including the Winter Park Chain of Lakes for boating, fishing, and kayaking, as well as nearby parks like Lake Baldwin Park with its dog-friendly trails, pavilions, and picnic areas. Lake Florence Preserve is a single-family home community in Winter Park, Florida, built between 2018 and 2019 by K. Hovnanian Homes. It currently has 3 single family homes for sale with an average list price of $1,196,633.33. The homes range in size from 2,193 ft2 to 4,173 ft2. The HOA fees range from $179 to $186 per month. The average annual property tax for Lake Florence Preserve is $7,808.63. It is located in Seminole County.
Lake Forest Park Lake Forest Park is a serene and family-oriented neighborhood renowned for its quiet, tree-lined streets, walkability, and strong sense of community, making it an ideal haven for residents seeking suburban tranquility near the bustling amenities of downtown. This southwest gem, bordered by Kenilworth Shores to the south and Baldwin Park to the east, offers an array of neighborhood perks including dog-friendly green spaces and parks perfect for leisurely strolls or playtime with pets, while its proximity to the Winter Park Chain of Lakes provides easy access to boating, kayaking, fishing, and scenic waterfront paths. Families and pet owners alike appreciate the area's safety and accessibility to upscale shopping along Park Avenue, elegant dining options, and cultural hotspots like the Charles Hosmer Morse Museum of American Art, all within a short walk or drive, blending everyday comfort with the vibrant, arts-infused lifestyle that defines this affluent enclave. Lake Forest Park is a single-family home community in Winter Park, Florida, built between 1952 and 2026. It currently has 2 single family homes for sale with an average list price of $2,214,900. The homes range in size from 1,013 ft2 to 4,858 ft2. The average annual property tax for Lake Forest Park is $5,334.40.	Median Price: $588,250
Lake Killarney Condominiums Lake Killarney Condominiums, located at 151 N Orlando Ave in Winter Park, FL, offers a serene lakeside living experience in the charming Fairview neighborhood. This two-story complex with 121 units provides residents with a blend of tranquility and urban convenience, just five miles from Orlando. The community boasts an array of amenities, including a private lakefront park with a boat dock featuring approximately 14 slips, a boat ramp, and facilities for wakeboarding, waterskiing, and seaplane landings. Residents can enjoy a waterfront swimming pool, shuffleboard courts, a well-equipped gym, and a large lawn with Adirondack chairs, grills, and picnic tables for social gatherings. Additional perks include bike racks, a game room, multiple laundry rooms, community storage, recycling facilities, and pet-friendly policies, making Lake Killarney Condominiums an ideal choice for a relaxed, active lifestyle. Lake Killarney Condominiums is a condo building in Winter Park, Florida, built in 1960. It currently has 5 condos for sale with an average list price of $319,799.80. The homes range in size from 582 ft2 to 1,875 ft2. The HOA fees range from $305 to $708 per month. The average annual property tax for Lake Killarney Condominiums is $1,932.62. It is located in Orange County.	Median Price: $260,000
Lake Knowles Terrace Lake Knowles Terrace is a single-family home community in Winter Park, Florida, built between 1925 and 2025. It currently has 5 single family homes for sale with an average list price of $2,040,600. The homes range in size from 864 ft2 to 4,582 ft2. The average annual property tax for Lake Knowles Terrace is $8,944.79. It is located in Orange County.	Median Price: $1,100,000
Lake Spier Crossing Lake Spier Crossing is a townhouse community in Winter Park, Florida, built between 2023 and 2024. It currently has 1 townhouse for sale with a list price of $819,700. The homes range in size from 2,051 ft2 to 2,104 ft2. The HOA fees range from $300 to $300 per month. The average annual property tax for Lake Spier Crossing is $2,109.06. It is located in Orange County.	Median Price: $850,000
Lake Virginia Condominiums Nestled along the serene shores of Lake Virginia, the Lake Virginia Condominiums community offers an idyllic lakeside lifestyle enveloped by the scenic Winter Park Chain of Lakes. Residents revel in a wealth of upscale amenities designed to foster relaxation and recreation, including a luxurious lakefront pool and spa with breathtaking water views, a soothing sauna, and a fire pit paired with a gas grill for al fresco gatherings. The community clubhouse serves as a vibrant social hub with a party room, while a fitness center and exercise room cater to wellness enthusiasts. Outdoor pursuits abound with a private dock for boating, storage for small watercraft, a dedicated dog walk area, and bike storage for exploring the neighborhood. Additional conveniences like a rentable guest suite, landscaped sun deck, and covered parking enhance the effortless elegance of daily living, all within easy reach of Park Avenue's charming shops and dining. Lake Virginia Condominiums is a condo building in Winter Park, Florida, built in 1969. It currently has no homes for sale. The homes range in size from 850 ft2 to 1,998 ft2. The HOA fees range from $713 to $1,346 per month. The average annual property tax for Lake Virginia Condominiums is $4,045.92. It is located in Orange County.	Median Price: $417,100
Lake Waunatta Cove Lake Waunatta Cove is a single-family home community in Winter Park, Florida, built between 1963 and 1987. It currently has 2 single family homes for sale with an average list price of $541,000. The homes range in size from 1,520 ft2 to 2,615 ft2. The HOA fees range from $15 to $15 per month. The average annual property tax for Lake Waunatta Cove is $4,603.04. It is located in Orange County.	Median Price: $500,000
Lake Waunatta Village Lake Waunatta Village is a single-family home community in Winter Park, Florida, built between 1976 and 1978. It currently has 1 single family home for sale with a list price of $975,000. The homes range in size from 1,793 ft2 to 3,858 ft2. The HOA fees range from $7 to $7 per month. The average annual property tax for Lake Waunatta Village is $3,148.57. It is located in Orange County.
Lake Waunatta Woods Lake Waunatta Woods is a serene lakeside neighborhood centered around Lake Waunatta, a pristine spring-fed body of water that anchors the community’s tranquil charm and natural beauty. Residents cherish the area’s family-friendly vibe, where dog-friendly paths wind through quiet streets ideal for leisurely walks and casual strolls, fostering a strong sense of community among neighbors who bond over shared interests in gardening, hiking, and outdoor pursuits. Key amenities include private boat docks with electric lifts for effortless kayaking or leisurely boating excursions across Lake Waunatta’s calm surface, expansive entertaining decks perfect for barbecues and gatherings, and stunning waterfront views that enhance every home’s appeal. Just minutes from Winter Park’s bustling downtown, the neighborhood offers convenient access to charming boutiques, exquisite dining options, and year-round cultural events, blending lakeside relaxation with an active, connected lifestyle. Lake Waunatta Woods is a single-family home community in Winter Park, Florida, built between 1974 and 1984. It currently has 1 single family home for sale with a list price of $689,000. The homes range in size from 1,892 ft2 to 5,329 ft2. The HOA fees range from $21 to $28 per month. The average annual property tax for Lake Waunatta Woods is $4,549.89. It is located in Orange County.	Median Price: $593,000
Lakemont Heights Lakemont Heights is a single-family home community in Winter Park, Florida, built between 1953 and 2024. It currently has 1 single family home for sale with a list price of $425,000. The homes range in size from 1,050 ft2 to 2,843 ft2. The HOA fees range from $4 to $4 per month. The average annual property tax for Lakemont Heights is $3,574.59. It is located in Orange County.	Median Price: $465,000
Lakeside Estates Lakeside Estates is a serene gated community that embodies upscale lakeside living between the tranquil Garden Lake and Bear Gully Lake. Lakeside Estates offers an inviting retreat where leisurely strolls along the water's edge and community gatherings foster a true sense of neighborhood warmth. Lakeside Estates is a single-family home community in Winter Park, Florida, built between 2014 and 2015. It currently has 2 single family homes for sale with an average list price of $1,437,495. The homes range in size from 3,057 ft2 to 5,111 ft2. The HOA fees range from $150 to $178 per month. The average annual property tax for Lakeside Estates is $8,229.80. It is located in Seminole County.	Median Price: $1,132,500
Lakeside Manor Nestled on the serene shores of Lake Killarney, Lakeside Manor offers residents an idyllic lakeside retreat blending natural beauty with modern conveniences. This charming condominium community captivates with its resort-style amenities, including a sparkling lakefront pool perfect for leisurely swims under the Florida sun, a welcoming clubhouse ideal for social gatherings and relaxation, and a private boat ramp and dock that invite seamless exploration of the scenic Winter Park Chain of Lakes. Outdoor enthusiasts delight in the barbecue grills and picnic tables scattered across lush, well-maintained grounds, fostering a strong sense of community amid stunning waterfront views. Practical perks abound with on-site laundry facilities and storage options, while the prime location provides effortless access to Winter Park's vibrant downtown, featuring upscale boutiques, diverse dining, and cultural attractions just minutes away. Lakeside Manor is a condo community in Winter Park, Florida, built in 1969. It currently has 7 condos for sale with an average list price of $183,141.43. The homes range in size from 645 ft2 to 1,050 ft2. The HOA fees range from $171 to $385 per month. The average annual property tax for Lakeside Manor is $1,620.67. It is located in Orange County.	Median Price: $197,450
Lancelot at Winter Park Lancelot at Winter Park offers residents a serene retreat with an array of inviting amenities designed for modern living. The community features a sparkling community pool perfect for leisurely swims or sunny afternoons, complemented by a clubhouse ideal for social gatherings and relaxation. Lancelot at Winter Park is a condo community in Winter Park, Florida, built in 1990. It currently has 2 condos for sale with an average list price of $175,950. The homes range in size from 840 ft2 to 940 ft2. The HOA fees range from $279 to $370 per month. The average annual property tax for Lancelot at Winter Park is $1,285.24. It is located in Orange County.	Median Price: $170,000
Laurel Springs Laurel Springs is a single-family home community in Winter Park, Florida, built between 1972 and 1979. It currently has 2 single family homes for sale with an average list price of $422,450. The homes range in size from 1,106 ft2 to 1,906 ft2. The average annual property tax for Laurel Springs is $2,741.97. It is located in Orange County.	Median Price: $427,450
Lawndale Lawndale is a single-family home community in Winter Park, Florida, built between 1925 and 2026. It currently has 4 single family homes for sale with an average list price of $1,219,950 and 1 lot for sale with a list price of $385,000. The homes range in size from 564 ft2 to 3,267 ft2. The HOA fees range from $89 to $89 per month. The average annual property tax for Lawndale is $3,562.05. It is located in Orange County.	Median Price: $425,000
Lazy Oaks Lazy Oaks is a condo and townhouse community in Winter Park, Florida, built between 1981 and 1985. It currently has no homes for sale. The homes range in size from 1,008 ft2 to 1,538 ft2. The HOA fees range from $218 to $325 per month. The average annual property tax for Lazy Oaks is $1,772.61. It is located in Seminole County.	Median Price: $267,500
Lost Creek Lost Creek is a single-family home community in Winter Park, Florida, built between 1980 and 2000. It currently has 3 single family homes for sale with an average list price of $618,605. The homes range in size from 1,906 ft2 to 3,401 ft2. The HOA fees range from $10 to $23 per month. The average annual property tax for Lost Creek is $3,222.58. It is located in Seminole County.	Median Price: $501,000
Lugano Terrace Lugano Terrace is a single-family home community in Winter Park, Florida, built between 1960 and 2003. It currently has 3 single family homes for sale with an average list price of $2,248,333.33. The homes range in size from 1,894 ft2 to 6,854 ft2. The average annual property tax for Lugano Terrace is $10,495.11. It is located in Orange County.	Median Price: $1,105,000
Maitland Shores Nestled along the serene shores of Lake Maitland, Maitland Shores is a picturesque lakeside neighborhood renowned for its tranquil blend of natural beauty and upscale suburban living. Residents relish exclusive lakefront access to the Winter Park Chain of Lakes, perfect for boating, kayaking, fishing, and leisurely waterfront strolls amid lush, mature trees and scenic views. The community fosters a strong sense of camaraderie while offering convenient proximity to vibrant amenities, including the esteemed Winter Park Racquet Club for tennis enthusiasts, the charming boutiques and gourmet dining along Park Avenue, cultural gems like the Orlando Museum of Art and the Winter Park Public Library, and nearby parks such as Mead Gardens with its subtropical trails and the blooming Kraft Azalea Gardens. Easy connections to major highways, hospitals, and Rollins College further enhance the lifestyle, making Maitland Shores an idyllic haven for those seeking both relaxation and refined recreation in Central Florida's most enchanting enclave. Maitland Shores is a single-family home community in Winter Park, Florida, built between 1925 and 2018. It currently has 6 single family homes for sale with an average list price of $2,430,825. The homes range in size from 1,368 ft2 to 8,082 ft2. The HOA fees range from $6 to $120 per month. The average annual property tax for Maitland Shores is $15,754.75. It is located in Orange County.	Median Price: $1,400,000
Mead Garden Condominiums Mead Garden Condominiums is a condo community in Winter Park, Florida, built in 1967. It currently has 2 condos for sale with an average list price of $227,450. The homes range in size from 653 ft2 to 913 ft2. The HOA fees range from $226 to $409 per month. The average annual property tax for Mead Garden Condominiums is $1,790.67. It is located in Orange County.	Median Price: $220,000
Meadows at Hawks Crest Meadows at Hawks Crest is a single-family home community in Winter Park, Florida, built between 2019 and 2022 by Taylor Morrison. It currently has no homes for sale. The homes range in size from 1,589 ft2 to 2,894 ft2. The HOA fees range from $174 to $936 per month. The average annual property tax for Meadows at Hawks Crest is $2,624.52. It is located in Seminole County.
Merrie Oaks Village Merrie Oaks Village is a townhouse community in Winter Park, Florida, built in 1973. It currently has no homes for sale. The homes range in size from 1,727 ft2 to 2,019 ft2. The HOA fees range from $150 to $167 per month. The average annual property tax for Merrie Oaks Village is $1,813.15. It is located in Orange County.	Median Price: $390,000
Morseland Morseland is a single-family home community in Winter Park, Florida, built between 1953 and 2015. It currently has 3 single family homes for sale with an average list price of $820,000. The homes range in size from 1,115 ft2 to 2,964 ft2. The HOA fees range from $8 to $25 per month. The average annual property tax for Morseland is $7,483.91. It is located in Orange County.	Median Price: $1,628,250
Morseland Gardens Morseland Gardens is a single-family home community in Winter Park, Florida, built between 1953 and 2004. It currently has no homes for sale. The homes range in size from 2,691 ft2 to 4,733 ft2. The average annual property tax for Morseland Gardens is $19,322.46. It is located in Orange County.
Northwood Terrace Northwood Terrace is a single-family home community in Winter Park, Florida, built between 1953 and 2026. It currently has 3 single family homes for sale with an average list price of $1,729,666.67. The homes range in size from 1,230 ft2 to 3,590 ft2. The average annual property tax for Northwood Terrace is $4,087.60. It is located in Orange County.	Median Price: $610,000
Oakcrest Oakcrest is a single-family home community in Winter Park, Florida, built between 1980 and 1984. It currently has no homes for sale. The homes range in size from 1,080 ft2 to 1,620 ft2. The average annual property tax for Oakcrest is $2,086.18. It is located in Seminole County.	Median Price: $390,000
Oaks Condominiums Oaks Condominiums is a condo community in Winter Park, Florida, built in 1973. It currently has no homes for sale. The homes have an average size of 987 ft2. The HOA fees range from $350 to $400 per month. The average annual property tax for Oaks Condominiums is $1,587.99. It is located in Orange County.
Orange Grove Orange Grove is a single-family home community in Winter Park, Florida, built between 1977 and 2024. It currently has no homes for sale. The homes range in size from 1,087 ft2 to 3,150 ft2. The average annual property tax for Orange Grove is $4,626.44. It is located in Orange County.	Median Price: $520,000
Orange Terrace Orange Terrace is a single-family home community in Winter Park, Florida, built between 1942 and 1955. It currently has 1 single family home for sale with a list price of $450,000. The homes range in size from 1,178 ft2 to 1,718 ft2. The average annual property tax for Orange Terrace is $2,746.02. It is located in Orange County.	Median Price: $449,000
Orangewood Park Orangewood Park is a single-family home community in Winter Park, Florida, built between 1952 and 1954. It currently has 1 single family home for sale with a list price of $675,000. The homes range in size from 1,015 ft2 to 1,925 ft2. The average annual property tax for Orangewood Park is $3,506.08. It is located in Orange County.	Median Price: $550,000
Osceola Court Osceola Court is a single-family home community in Winter Park, Florida, built between 1912 and 1948. It currently has no homes for sale. The homes range in size from 1,562 ft2 to 3,019 ft2. The average annual property tax for Osceola Court is $7,718.51. It is located in Orange County.	Median Price: $1,100,000
Osceola Heights Osceola Heights is a single-family home community in Winter Park, Florida, built between 1930 and 2003. It currently has 1 single family home for sale with a list price of $455,000. The homes range in size from 640 ft2 to 3,658 ft2. The average annual property tax for Osceola Heights is $6,097.98. It is located in Orange County.	Median Price: $805,000
Osceola Shores Osceola Shores is a single-family home community in Winter Park, Florida, built between 1876 and 2022. It currently has 2 single family homes for sale with an average list price of $2,650,000. The homes range in size from 2,051 ft2 to 5,847 ft2. The average annual property tax for Osceola Shores is $15,285.10. It is located in Orange County.	Median Price: $3,818,750
Osceola Summit Residents enjoy proximity to the upscale Park Avenue District, just a short drive or walk away, where world-renowned boutique shopping, award-winning restaurants, and cultural attractions like museums and art galleries await. The neighborhood’s location near the Winter Park Chain of Lakes provides opportunities for outdoor activities such as boating, kayaking, and scenic tours, with some properties offering lakefront access and private boat slips. Additionally, Osceola Summit is close to top-rated schools, parks like Mead Botanical Garden, and recreational facilities, making it a perfect choice for families and professionals seeking a vibrant yet peaceful lifestyle. Osceola Summit is a single-family home community in Winter Park, Florida, built between 1938 and 2008. It currently has 2 single family homes for sale with an average list price of $1,674,000. The homes range in size from 1,382 ft2 to 6,008 ft2. The average annual property tax for Osceola Summit is $16,708.93. It is located in Orange County.	Median Price: $1,750,000
Oxford Cove Oxford Cove is a single-family home community in Winter Park, Florida, built in 2000. It currently has no homes for sale. The homes have an average size of 2,679 ft2. The HOA fees range from $29 to $29 per month. The average annual property tax for Oxford Cove is $6,613. It is located in Orange County.
Palmer Park Palmer Park is a single-family home community in Winter Park, Florida, built between 1955 and 2020. It currently has no homes for sale. The homes range in size from 2,230 ft2 to 4,767 ft2. The average annual property tax for Palmer Park is $14,790.60. It is located in Orange County.	Median Price: $2,650,000
Park Aire Park Aire stands as a charming Art Deco condominium complex, evoking the timeless elegance of mid-century design with its pink-hued stucco facade and courtyard layout. Residents enjoy a host of thoughtful amenities that enhance the lock-and-leave lifestyle, including a private pool area with a sunbathing deck and serene Zen garden, reserved underground parking for effortless access, an on-site laundry facility, and a community room ideal for gatherings. Additional conveniences abound, such as a rentable guest suite for visitors, a lovely third-floor sun deck and patio for relaxation, and cable television throughout. Surrounded by lush greenery and offering stunning views of nearby landmarks like Casa Feliz, St. Margaret Mary Church, and the Winter Park Country Club, Park Aire provides an effortless gateway to the area's vibrant scene, from strolling to boutique shops and fine dining to attending art festivals, Morse Museum exhibits, and scenic boat tours on the Chain of Lakes. Park Aire is a condo building in Winter Park, Florida, built in 1956. It currently has no homes for sale. The homes range in size from 539 ft2 to 986 ft2. The HOA fees range from $223 to $655 per month. The average annual property tax for Park Aire is $3,441.50. It is located in Orange County.
Park Green Park Green is a townhouse community in Winter Park, Florida, built between 1982 and 1992. It currently has 2 townhouses for sale with an average list price of $377,000. The homes range in size from 1,226 ft2 to 2,020 ft2. The HOA fees range from $122 to $327 per month. The average annual property tax for Park Green is $2,079.35. It is located in Orange County.	Median Price: $420,000
Park Grove Park Grove is a single-family home community in Winter Park, Florida, built between 1960 and 2026. It currently has 1 single family home for sale with a list price of $4,750,000. The homes range in size from 2,063 ft2 to 5,375 ft2. The HOA fees range from $13 to $21 per month. The average annual property tax for Park Grove is $7,870.37. It is located in Orange County.	Median Price: $1,942,000
Park Manor Park Manor is a single-family home community in Winter Park, Florida, built between 1959 and 2025. It currently has 1 single family home for sale with a list price of $1,450,000. The homes range in size from 1,392 ft2 to 3,161 ft2. The average annual property tax for Park Manor is $2,113.59. It is located in Orange County.	Median Price: $500,000
Park North Park North is a single-family home community in Winter Park, Florida, built between 1968 and 1972. It currently has no homes for sale. The homes range in size from 2,702 ft2 to 3,096 ft2. The average annual property tax for Park North is $11,243.33. It is located in Orange County.	Median Price: $1,115,000
Park Shore Residents enjoy convenient access to the city's renowned amenities, including the tranquil Winter Park Chain of Lakes for scenic boat tours and water recreation, as well as inviting public parks like Kraft Azalea Garden and Lake Baldwin Park, which offer shaded trails, gardens, and off-leash areas for pets. The area boasts upscale shopping and dining along vibrant Park Avenue, cultural gems such as the Orlando Museum of Art and the Albin Polasek Museum, and recreational pursuits at local golf courses and the Cady Way Trail. With its walkable green spaces, nearby healthcare facilities, and a vibrant calendar of neighborhood events and farmers' markets, Park Shore provides an idyllic blend of relaxation and refined living in this beloved Central Florida enclave. Park Shore is a townhouse community in Winter Park, Florida, built in 2019. It currently has 2 townhouses for sale with an average list price of $662,000. The homes range in size from 1,852 ft2 to 1,866 ft2. The HOA fees range from $275 to $498 per month. The average annual property tax for Park Shore is $4,610.19. It is located in Orange County.
Park West Park West Condominiums offers a serene and upscale residential enclave surrounded by lush, beautifully landscaped grounds and enveloped by a fully fenced, gated perimeter for enhanced security and tranquility. Residents delight in an array of premium community amenities designed for relaxation and recreation, including an oversized swimming pool perfect for leisurely laps or sun-soaked afternoons, a newly renovated clubhouse equipped with a full kitchen and billiard room ideal for social gatherings and entertaining, lighted tennis courts for spirited matches under the stars, and a convenient on-site car wash station to keep vehicles pristine. With assigned under-building parking, ample guest spaces, and effortless elevator access, everyday living here seamlessly blends convenience with the charm of Winter Park's vibrant cultural scene and scenic lakefront allure. Park West is a condo community in Winter Park, Florida, built between 1981 and 2006. It currently has 1 condo for sale with a list price of $569,000. The homes range in size from 1,151 ft2 to 2,347 ft2. The HOA fees range from $349 to $1,126 per month. The average annual property tax for Park West is $4,575.59. It is located in Orange County.	Median Price: $688,350
Parklando Parklando is a single-family home community in Winter Park, Florida, built between 1926 and 2026. It currently has 2 single family homes for sale with an average list price of $2,119,250. The homes range in size from 962 ft2 to 3,412 ft2. The average annual property tax for Parklando is $6,209.45. It is located in Orange County.	Median Price: $799,000
Parkview Village Parkview Village stands as a serene and inviting condominium community nestled amid lush, mature landscaping and scenic views, offering residents a peaceful retreat just minutes from the vibrant cultural heart of the city and its renowned chain of interconnected lakes ideal for boating and water pursuits. This pet-friendly haven emphasizes outdoor leisure with a sparkling community pool, relaxing hot tub, and beautifully maintained grounds that encourage leisurely strolls and gatherings. Each home features private screened patios, providing shaded sanctuaries for al fresco dining or quiet evenings under the stars, while the overall design fosters a sense of comfort and convenience in a location brimming with easy access to nearby shopping centers, educational institutions like Full Sail University, and the eclectic charm of Winter Park's tree-lined streets. Parkview Village is a condo community in Winter Park, Florida, built in 1984. It currently has 9 condos for sale with an average list price of $182,655.56. The homes range in size from 749 ft2 to 1,105 ft2. The HOA fees range from $110 to $442 per month. The average annual property tax for Parkview Village is $1,495.82. It is located in Orange County.	Median Price: $185,000
Pelican Bay Pelican Bay stands as a picturesque lakeside subdivision where residents revel in the tranquil allure of private spring-fed waters ideal for boating and skiing. This exclusive enclave offers an array of upscale amenities designed for leisurely living, including expansive private docks for effortless lake access, jetted hot tubs overlooking shimmering sunsets, and meticulously landscaped grounds enhanced by economical lake-fed irrigation systems. Community perks extend to communal parks and recreational facilities maintained through dedicated homeowners' association efforts, fostering a sense of camaraderie amid lush greenery. Pelican Bay is a single-family home community in Winter Park, Florida, built between 1982 and 1986. It currently has 2 single family homes for sale with an average list price of $729,475. The homes range in size from 1,844 ft2 to 3,121 ft2. The HOA fees range from $29 to $42 per month. The average annual property tax for Pelican Bay is $4,497.05. It is located in Seminole County.
Penn Place Penn Place is an exclusive enclave of 28 custom-built luxury townhomes nestled on a serene, tree-lined street, offering a perfect blend of privacy and proximity to the vibrant Park Avenue and Winter Park Golf Course. This highly sought-after neighborhood, developed by Hill Gray Seven, features residences with premium amenities, including private courtyards, elevators, private balconies. Residents enjoy a quaint neighborhood park, fenced yards with sprinkler systems, and attached two-car garages with private alley access, all within walking distance to downtown Winter Park’s charming restaurants, boutiques, and cultural attractions. Penn Place is a townhouse community in Winter Park, Florida, built in 2016. It currently has no homes for sale. The homes range in size from 3,023 ft2 to 3,345 ft2. The HOA fees range from $925 to $936 per month. The average annual property tax for Penn Place is $12,002.12.
Pennsylvania Place Pennsylvania Place's prime location enhances its appeal, providing easy access to Winter Park's vibrant downtown scene, including upscale shops, diverse dining options, cultural arts venues, and scenic lakeside paths, all while fostering a strong sense of community in this charming enclave of Central Florida. Pennsylvania Place is a single-family home community in Winter Park, Florida, built between 2000 and 2007. It currently has 1 single family home for sale with a list price of $2,695,000. The homes range in size from 2,607 ft2 to 4,888 ft2. The HOA fees range from $159 to $222 per month. The average annual property tax for Pennsylvania Place is $12,974.92. It is located in Orange County.	Median Price: $2,144,000
Pennsylvania Place Townhomes Pennsylvania Place Townhomes is a townhouse community in Winter Park, Florida, built in 1984. It currently has no homes for sale. The homes have an average size of 2,095 ft2. The HOA fees range from $200 to $200 per month. The average annual property tax for Pennsylvania Place Townhomes is $5,916. It is located in Orange County.
Perle Du Lac Nestled along the serene north shore of Lake Virginia, Perle Du Lac—meaning "Pearl of the Lake"—embodies elegant French Revivalist charm with its distinctive mansard roofs and towering windows that frame breathtaking waterfront views. This exclusive condominium community captivates residents with meticulously sculpted gardens that envelop a tranquil lakeside pool, where one can unwind amid lush greenery and gentle lake breezes. Enhancing the lakeside lifestyle, a private dock and deeded boat slips invite effortless exploration of the Chain of Lakes by water, while the grand interiors boast soaring architectural ceilings, luxurious stone and hardwood floors, recessed lighting that casts a warm glow over open living spaces, and gourmet kitchens designed for culinary inspiration. Perle Du Lac offers a refined retreat that seamlessly blends sophisticated living with the natural allure of Central Florida's most picturesque waterways. Perle Du Lac is a condo community in Winter Park, Florida, built between 1999 and 2003. It currently has 1 condo for sale with a list price of $2,295,000. The homes range in size from 2,290 ft2 to 2,715 ft2. The HOA fees range from $885 to $1,392 per month. The average annual property tax for Perle Du Lac is $12,015.20. It is located in Orange County.	Median Price: $2,250,000
Quail Hollow Quail Hollow is a single-family home community in Winter Park, Florida, built between 1972 and 1976. It currently has no homes for sale. The homes range in size from 1,981 ft2 to 3,912 ft2. The HOA fees range from $200 to $200 per month. The average annual property tax for Quail Hollow is $5,971.38. It is located in Orange County.
Quail Run Quail Run is a single-family home community in Winter Park, Florida, built between 1986 and 1995. It currently has 1 single family home for sale with a list price of $624,999. The homes range in size from 2,016 ft2 to 3,400 ft2. The HOA fees range from $17 to $48 per month. The average annual property tax for Quail Run is $4,107.43. It is located in Seminole County.	Median Price: $435,000
Ridge High Ridge High is a single-family home community in Winter Park, Florida, built between 1958 and 1971. It currently has 1 single family home for sale with a list price of $429,000. The homes range in size from 998 ft2 to 3,020 ft2. The HOA fees range from $1 to $1 per month. The average annual property tax for Ridge High is $2,102.09. It is located in Seminole County.	Median Price: $365,000
Roundelay Roundelay is a single-family home community in Winter Park, Florida, built in 1910. It currently has no homes for sale. The homes have an average size of 4,720 ft2. The average annual property tax for Roundelay is $11,258. It is located in Orange County.
Sanctuary at Aloma Sanctuary at Aloma is a single-family home community in Winter Park, Florida, built between 2014 and 2015. It currently has 1 single family home for sale with a list price of $719,000. The homes range in size from 2,265 ft2 to 3,152 ft2. The HOA fees range from $115 to $182 per month. The average annual property tax for Sanctuary at Aloma is $5,042.26. It is located in Seminole County.
Sanctuary at Lake Ann Sanctuary at Lake Ann is a single-family home community in Winter Park, Florida, built between 2006 and 2007. It currently has 1 single family home for sale with a list price of $950,000. The homes range in size from 2,838 ft2 to 3,119 ft2. The HOA fees range from $208 to $208 per month. The average annual property tax for Sanctuary at Lake Ann is $6,022.81. It is located in Seminole County.
Sevilla The Sevilla neighborhood exudes timeless charm with its tree-lined streets, moss-draped canopies, and beautifully landscaped yards that create a serene, picturesque escape. Residents cherish the community's dog-friendly atmosphere, welcoming playgrounds, and convenient dog park, fostering a strong sense of neighborly connection and family-oriented living. The area boasts easy access to an array of outdoor pursuits, including nearby parks, scenic trails for walking and biking, and proximity to premier golf courses like Winter Park Golf Course and Winter Pines Golf Club, alongside lakefront views of Lake Sue that enhance leisurely strolls. Everyday conveniences abound with abundant shopping at Hollieanna Shopping Center and Winter Park Village, diverse dining options, and vibrant cultural spots in Downtown Winter Park, all within a short distance, making Sevilla an idyllic blend of peaceful retreat and lively accessibility. Sevilla is a single-family home community in Winter Park, Florida, built between 1971 and 1983. It currently has 2 single family homes for sale with an average list price of $2,185,000. The homes range in size from 2,565 ft2 to 5,429 ft2. The HOA fees range from $42 to $82 per month. The average annual property tax for Sevilla is $10,747.57. It is located in Orange County.	Median Price: $1,305,000
Seville Park Seville Park is a townhouse, single-family home, and condo community in Winter Park, Florida, built between 1945 and 2016. It currently has 1 single family home for sale with a list price of $575,000. The homes range in size from 736 ft2 to 1,945 ft2. The HOA fees range from $100 to $400 per month. The average annual property tax for Seville Park is $3,505.45. It is located in Orange County.
Sicilian Shores Nestled along the serene western shores of Lake Maitland, Sicilian Shores captivates with its exclusive enclave of waterfront estates, where brick-lined streets evoke the charm of European villas amid lush canopies of ancient oaks, evergreens, and vibrant tropical blooms. Residents revel in direct lakefront access, ideal for boating and watersports on the pristine Winter Park Chain of Lakes, just moments from their doorsteps. Proximity to the esteemed Winter Park Racquet Club enhances leisure pursuits, offering tennis courts, a sparkling pool for lounging, and opportunities to forge lasting memories in this vibrant social hub. Sicilian Shores is a single-family home community in Winter Park, Florida, built between 1954 and 2022. It currently has 1 single family home for sale with a list price of $4,500,000. The homes range in size from 3,242 ft2 to 7,644 ft2. The average annual property tax for Sicilian Shores is $22,945.50. It is located in Orange County.	Median Price: $2,900,000
Slovak Village Slovak Village is a single-family home and townhouse community in Winter Park, Florida, built between 1949 and 2023. It currently has 1 single family home for sale with a list price of $337,500. The homes range in size from 1,289 ft2 to 1,782 ft2. The HOA fees range from $275 to $275 per month. The average annual property tax for Slovak Village is $2,160.76. It is located in Seminole County.	Median Price: $467,000
South Interlachen Place South Interlachen Place is an exclusive enclave of luxury townhomes nestled in the heart of Winter Park, Florida, offering residents a serene retreat just steps from the vibrant energy of downtown. The development features upscale living with private rooftop terraces ideal for outdoor lounging, elevators for convenient access, and lush privacy landscaping that enhances the sense of seclusion. Surrounding the area, residents can enjoy upscale shopping and dining along Park Avenue, scenic boat tours on the nearby Chain of Lakes, cultural visits to the Morse Museum of Art, and recreational pursuits like fishing or strolling through Central Park. South Interlachen Place is a condo building in Winter Park, Florida, built between 2016 and 2020. It currently has no homes for sale. The homes range in size from 3,244 ft2 to 4,160 ft2. The HOA fees range from $1,133 to $1,367 per month. The average annual property tax for South Interlachen Place is $25,991.78. It is located in Orange County.
South Lakemont Shores Nestled along the serene shores of Lake Spier, South Lakemont Shores offers a tranquil lakeside retreat ideal for those seeking a peaceful yet connected lifestyle. This charming neighborhood boasts stunning water views that invite daily strolls along shady tree-lined paths, fostering a sense of calm and natural beauty. Residents enjoy easy access to nearby community perks, including the inviting Baldwin Park dog park just across South Lakemont Avenue, perfect for leisurely outings with pets or neighbors. The area's prime location enhances everyday living with convenient proximity to vibrant local events, top-rated schools, and seamless connections via major highways like I-4, 408, and 417, opening doors to Central Florida's cultural hotspots, fine dining, and entertainment in Downtown Orlando and beyond. Whether unwinding by the water or exploring the surrounding enclaves of Baldwin Park and Winter Park, South Lakemont Shores embodies a harmonious blend of quiet elegance and effortless accessibility. South Lakemont Shores is a single-family home community in Winter Park, Florida, built between 1957 and 2024. It currently has 1 single family home for sale with a list price of $1,950,000. The homes range in size from 1,366 ft2 to 4,100 ft2. The average annual property tax for South Lakemont Shores is $5,369.10. It is located in Orange County.	Median Price: $2,800,000
Springview Springview is a single-family home community in Winter Park, Florida, built between 1984 and 1985. It currently has no homes for sale. The homes range in size from 1,168 ft2 to 1,696 ft2. The average annual property tax for Springview is $2,415.93. It is located in Seminole County.	Median Price: $402,500
Stansbury Estates Stansbury Estates is a single-family home community in Winter Park, Florida, built between 1940 and 1961. It currently has 2 single family homes for sale with an average list price of $271,500. The homes range in size from 762 ft2 to 1,389 ft2. The average annual property tax for Stansbury Estates is $2,289.24. It is located in Orange County.	Median Price: $312,000
Stonehurst Estates Stonehurst Estates is a single-family home community in Winter Park, Florida, built between 1956 and 2001. It currently has no homes for sale. The homes range in size from 2,489 ft2 to 5,097 ft2. The average annual property tax for Stonehurst Estates is $12,490.21. It is located in Orange County.	Median Price: $2,280,000
Suburban Homes Suburban Homes is a single-family home community in Winter Park, Florida, built between 1949 and 2019. It currently has 1 single family home for sale with a list price of $404,990. The homes range in size from 804 ft2 to 2,379 ft2. The average annual property tax for Suburban Homes is $2,289.09. It is located in Seminole County.	Median Price: $370,000
Sylvan Heights Sylvan Heights is a single-family home community in Winter Park, Florida, built between 1949 and 2024. It currently has 1 single family home for sale with a list price of $580,000. The homes range in size from 993 ft2 to 3,289 ft2. The average annual property tax for Sylvan Heights is $6,366.77. It is located in Orange County.	Median Price: $1,035,000
Sylvan Lake Shores Sylvan Lake Shores is a single-family home community in Winter Park, Florida, built between 1887 and 2025. It currently has 2 single family homes for sale with an average list price of $1,627,500. The homes range in size from 1,399 ft2 to 5,792 ft2. The average annual property tax for Sylvan Lake Shores is $8,396.17. It is located in Orange County.	Median Price: $1,180,000
Sylvan Park Sylvan Park is a single-family home community in Winter Park, Florida, built between 1915 and 2021. It currently has no homes for sale. The homes range in size from 1,647 ft2 to 4,627 ft2. The average annual property tax for Sylvan Park is $9,567.12. It is located in Orange County.	Median Price: $1,190,000
Tangerine Court Tangerine Court is a single-family home community in Winter Park, Florida, built between 1951 and 2025. It currently has 1 single family home for sale with a list price of $1,675,000. The homes range in size from 1,162 ft2 to 3,733 ft2. The average annual property tax for Tangerine Court is $5,833.88. It is located in Orange County.	Median Price: $595,000
Tanglewood Tanglewood, a serene and established neighborhood, offers residents an idyllic blend of mid-century charm and modern convenience, with tree-lined streets and spacious lots shaded by mature landscaping that create a peaceful, private retreat—many homes backing onto preserved green spaces without rear neighbors. Adjacent to the prestigious Interlachen Country Club, the community provides easy access to premier golfing and social pursuits, while its central location just seven miles north of Downtown Orlando ensures swift connections via nearby State Road 436, I-4, and the 408 expressway to world-famous attractions like Disney and Universal. Everyday luxuries abound with proximity to the vibrant Winter Park Village for eclectic dining, upscale shopping, a supermarket, and a movie theater, complemented by inviting nearby green spaces such as Phelps Park's shaded playground, picnic areas, and sports courts; the adjacent YMCA featuring fitness classes, youth programs, and a community pool; and the expansive Central Park, alive with annual festivals and events. Further enriching the lifestyle are cultural gems like Mead Botanical Garden, Kraft Azalea Garden, and the Albin Polasek Museum and Sculpture Gardens, all within a short stroll or drive, fostering a vibrant yet relaxed atmosphere ideal for those seeking refined Florida living without the constraints of a homeowners association. Tanglewood is a single-family home community in Winter Park, Florida, built between 1954 and 2025. It currently has 3 single family homes for sale with an average list price of $411,833.33. The homes range in size from 1,000 ft2 to 4,462 ft2. The HOA fees range from $1 to $1 per month. The average annual property tax for Tanglewood is $2,622.54. It is located in Seminole County.	Median Price: $410,000
Temple Colony Temple Colony is a single-family home community in Winter Park, Florida, built between 1987 and 1988. It currently has no homes for sale. The homes range in size from 2,070 ft2 to 2,436 ft2. The average annual property tax for Temple Colony is $3,557.67. It is located in Orange County.
Temple Estates Temple Estates offers an enchanting enclave of luxury residences surrounded by the timeless charm of brick streets, majestic live oak trees, and serene lakeside serenity. Residents enjoy a lifestyle defined by refined elegance, with private half-acre lots featuring lush tropical landscaping, expansive saltwater pools, and park-like backyards ideal for outdoor entertaining. Proximity to the vibrant Park Avenue district provides easy access to boutique shopping, artisanal bakeries, and upscale dining, while top-rated schools and nearby Lake Knowles enhance the community's appeal for those seeking both tranquility and convenience in this quintessential Florida haven. Temple Estates is a single-family home community in Winter Park, Florida, built between 1952 and 2020. It currently has no homes for sale. The homes range in size from 2,283 ft2 to 4,777 ft2. The average annual property tax for Temple Estates is $10,998.89. It is located in Orange County.	Median Price: $1,292,000
Temple Grove Temple Grove is a subdivision in Winter Park, Florida. It currently has no homes for sale. It is located in Orange County.
Temple Heights Temple Heights is a single-family home community in Winter Park, Florida, built between 1950 and 2019. It currently has 1 single family home for sale with a list price of $2,490,000. The homes range in size from 2,133 ft2 to 4,013 ft2. The average annual property tax for Temple Heights is $13,943.81. It is located in Orange County.	Median Price: $1,825,000
Temple Terrace Temple Terrace is a single-family home community in Winter Park, Florida, built between 1953 and 2026. It currently has 4 single family homes for sale with an average list price of $698,725. The homes range in size from 897 ft2 to 2,910 ft2. The average annual property tax for Temple Terrace is $3,101.91. It is located in Orange County.	Median Price: $370,000
The Cloisters The Cloisters is a charming mid-rise Mediterranean-style condominium community that embodies refined lakeside living. Residents revel in an array of upscale amenities designed for leisure and wellness, including a heated community pool and spa enveloped by lush, manicured grounds, a state-of-the-art fitness center, a clubhouse for social gatherings, and a putting green for casual golf enthusiasts. The on-site manager ensures seamless day-to-day operations, while the private lakefront park offers tranquil green spaces and boat docks with available slips, inviting water-based adventures right at your doorstep. Connected by picturesque breezeways adorned with wrought-iron railings, the community fosters a sense of elegance and connection, all within an easy stroll to Park Avenue's vibrant shops, cafes, and cultural gems. The Cloisters is a condo community in Winter Park, Florida, built in 1971. It currently has 4 condos for sale with an average list price of $963,500. The homes range in size from 901 ft2 to 2,286 ft2. The HOA fees range from $456 to $1,100 per month. The average annual property tax for The Cloisters is $6,297.40. It is located in Orange County.	Median Price: $762,500
The Douglas Grand at Winter Park The Douglas Grand at Winter Park, located in the heart of downtown Winter Park, Florida, offers an upscale living experience with a blend of luxury and convenience. This elegant 4-story condominium, modeled after classic East Coast brownstones, features 42 spacious 3-bedroom, 3-bath residences, including single-story flats and two-story townhomest. The property provides secure, gated parking with two reserved spaces per unit, often on the same floor for easy access. Its prime location, just across from Central Park and a short walk to Park Avenue’s shopping and dining, enhances the vibrant, urban lifestyle. The Douglas Grand at Winter Park is a condo community in Winter Park, Florida, built between 2008 and 2009. It currently has 2 condos for sale with an average list price of $1,352,000. The homes range in size from 2,599 ft2 to 3,778 ft2. The HOA fees range from $143 to $1,300 per month. The average annual property tax for The Douglas Grand at Winter Park is $12,845.95.	Median Price: $1,186,500
The Enclave at Hawks Crest The Enclave at Hawks Crest is a townhouse community in the Hawks Crest neighborhood of Winter Park, Florida, built between 2018 and 2023 by Meritage Homes and Taylor Morrison. It currently has 1 single family home for sale with a list price of $679,000 and 2 townhouses for sale with an average list price of $452,500. The homes range in size from 1,755 ft2 to 4,295 ft2. The HOA fees range from $82 to $320 per month. The average annual property tax for The Enclave at Hawks Crest is $3,662.87. It is located in Seminole County.	Median Price: $450,000
The Landings at Hawks Crest The Landings at Hawks Crest is a single-family home community in the Hawks Crest neighborhood of Winter Park, Florida, built between 2019 and 2023 by Meritage Homes and Taylor Morrison. It currently has 1 single family home for sale with a list price of $785,000 and 1 townhouse for sale with a list price of $460,000. The homes range in size from 1,770 ft2 to 3,094 ft2. The HOA fees range from $23 to $385 per month. The average annual property tax for The Landings at Hawks Crest is $3,376.29. It is located in Seminole County.	Median Price: $715,000
The Meadows at Hawks Crest The Meadows at Hawks Crest is a single-family home community in the Hawks Crest neighborhood of Winter Park, Florida, built between 2019 and 2022 by Taylor Morrison. It currently has 1 single family home for sale with a list price of $689,000. The homes range in size from 1,631 ft2 to 2,894 ft2. The HOA fees range from $123 to $364 per month. The average annual property tax for The Meadows at Hawks Crest is $3,439.17. It is located in Seminole County.	Median Price: $740,000
The Preserve at Hawks Crest The Preserve at Hawks Crest is a single-family home community in the Hawks Crest neighborhood of Winter Park, Florida, built between 2018 and 2020 by Meritage Homes. It currently has 2 single family homes for sale with an average list price of $799,000. The homes range in size from 1,908 ft2 to 4,266 ft2. The HOA fees range from $170 to $236 per month. The average annual property tax for The Preserve at Hawks Crest is $4,359.68. It is located in Seminole County.	Median Price: $800,000
The Quarters at Winter Park The Quarters at Winter Park is a condo and townhouse community in Winter Park, Florida, built between 1978 and 1981. It currently has 1 condo for sale with a list price of $675,000. The homes range in size from 1,468 ft2 to 2,083 ft2. The HOA fees range from $300 to $627 per month. The average annual property tax for The Quarters at Winter Park is $4,426.66. It is located in Orange County.	Median Price: $576,250
The Residences he Residences stands as an elegant condominium enclave just steps from the vibrant Park Avenue district, offering a seamless blend of luxury living and urban convenience. Residents enjoy an array of upscale amenities designed for refined relaxation and effortless sophistication, including round-the-clock concierge service for personalized assistance, robust 24-hour security to ensure peace of mind, a stunning rooftop pool and spa for leisurely sun-soaked afternoons, a spacious club room perfect for entertaining or quiet gatherings, and reserved underground parking for added ease. This full-service haven captures the essence of Winter Park's charming lifestyle, where tree-lined streets and cultural enclaves meet modern indulgences. The Residences is a condo building in Winter Park, Florida, built in 2005. It currently has 1 condo for sale with a list price of $3,250,000. The homes range in size from 3,355 ft2 to 5,430 ft2. The HOA fees range from $2,572 to $4,928 per month. The average annual property tax for The Residences is $22,649.44. It is located in Orange County.
The Stratford The Stratford offers a vibrant condominium community that blends comfort and convenience for its residents. Key amenities include a sparkling swimming pool ideal for leisurely swims or poolside relaxation, a state-of-the-art fitness center equipped for comprehensive workouts, and a welcoming clubhouse perfect for social gatherings and events. Sports enthusiasts appreciate the on-site tennis and pickleball courts, while the dedicated laundry facilities add everyday ease. A lush community park provides green space for picnics, play, or peaceful strolls, all enveloped in a well-maintained environment that fosters a sense of belonging and leisure just minutes from local shops, dining, and cultural hotspots. The Stratford is a condo community in Winter Park, Florida, built in 1973. It currently has 5 condos for sale with an average list price of $182,980. The homes range in size from 678 ft2 to 1,300 ft2. The HOA fees range from $224 to $465 per month. The average annual property tax for The Stratford is $1,106.27. It is located in Seminole County.	Median Price: $157,750
Timberlane Timberlane is a single-family home community in Winter Park, Florida, built between 1956 and 1958. It currently has 1 single family home for sale with a list price of $935,000. The homes range in size from 1,866 ft2 to 3,160 ft2. The average annual property tax for Timberlane is $5,400.18. It is located in Orange County.	Median Price: $1,093,099.50
Timberlane Shores Timberlane Shores is a single-family home community in Winter Park, Florida, built between 1957 and 2024. It currently has 2 single family homes for sale with an average list price of $1,097,450. The homes range in size from 1,545 ft2 to 5,317 ft2. The HOA fees range from $4 to $45 per month. The average annual property tax for Timberlane Shores is $9,008.91. It is located in Orange County.	Median Price: $1,525,000
Townhomes At Harper Place Townhomes At Harper Place is a townhouse community in Winter Park, Florida, built between 2005 and 2006. It currently has 1 townhouse for sale with a list price of $549,900. The homes range in size from 1,626 ft2 to 1,661 ft2. The HOA fees range from $200 to $300 per month. The average annual property tax for Townhomes At Harper Place is $3,191.67. It is located in Orange County.
Trinity Bay Trinity Bay is a single-family home community in Winter Park, Florida, built between 1985 and 1994. It currently has no homes for sale. The homes range in size from 1,414 ft2 to 2,400 ft2. The HOA fees range from $55 to $69 per month. The average annual property tax for Trinity Bay is $2,459.66. It is located in Seminole County.	Median Price: $436,000
Tuscania Tuscania is a single-family home community in Winter Park, Florida, built between 1957 and 2022. It currently has no homes for sale. The homes range in size from 1,845 ft2 to 6,338 ft2. The average annual property tax for Tuscania is $16,022.86. It is located in Orange County.	Median Price: $4,430,000
Tuscany Place Tuscany Place is a single-family home community in Winter Park, Florida, built between 1978 and 1979. It currently has no homes for sale. The homes range in size from 2,458 ft2 to 3,949 ft2. The HOA fees range from $48 to $104 per month. The average annual property tax for Tuscany Place is $8,379.20. It is located in Orange County.	Median Price: $1,125,000
Tuscany Terrace Tuscany Terrace is a single-family home community in Winter Park, Florida, built between 1957 and 2024. It currently has no homes for sale. The homes range in size from 2,285 ft2 to 5,479 ft2. The average annual property tax for Tuscany Terrace is $14,942.07. It is located in Orange County.	Median Price: $2,600,000
University Garden University Garden is a single-family home community in Winter Park, Florida, built in 1985. It currently has no homes for sale. The homes have an average size of 2,110 ft2. The average annual property tax for University Garden is $1,979. It is located in Orange County.
Valencia Terrace Valencia Terrace is a single-family home community in Winter Park, Florida, built between 1926 and 2021. It currently has 1 single family home for sale with a list price of $4,545,000. The homes range in size from 2,196 ft2 to 4,293 ft2. The average annual property tax for Valencia Terrace is $18,407.14. It is located in Orange County.
Via Lago Via Lago is a townhouse and condo community in Winter Park, Florida, built between 2007 and 2010. It currently has 2 townhouses for sale with an average list price of $349,499.50. The homes range in size from 1,554 ft2 to 1,893 ft2. The HOA fees range from $305 to $402 per month. The average annual property tax for Via Lago is $2,535.04. It is located in Orange County.
Via Lago at Hanging Moss Via Lago at Hanging Moss is a subdivision in Winter Park, Florida. It currently has no homes for sale. It is located in Orange County.
Villa Siena Villa Siena stands as an elegant Tuscan-inspired condominium community, offering residents a sophisticated blend of urban convenience and refined leisure just steps from the vibrant Park Avenue shops, dining, and cultural landmarks like the Alfond Inn. Embracing a maintenance-free lifestyle, it captivates with its array of upscale amenities designed for relaxation and connection, including secure underground parking, a state-of-the-art fitness center, and versatile conference and social rooms ideal for gatherings. The elegant clubhouse features a billiard room and bar, while exterior covered verandas and an intimate rooftop terrace provide serene outdoor escapes with panoramic views of Lake Osceola, fostering a sense of community amid lush, tree-lined surroundings. Villa Siena is a condo building in Winter Park, Florida, built between 2006 and 2008. It currently has no homes for sale. The homes range in size from 1,514 ft2 to 3,603 ft2. The HOA fees range from $606 to $1,646 per month. The average annual property tax for Villa Siena is $15,750.84. It is located in Orange County.	Median Price: $2,225,000
Villa View Park Villa View Park is a single-family home community in Winter Park, Florida, built between 1925 and 2015. It currently has 1 single family home for sale with a list price of $505,000. The homes range in size from 1,263 ft2 to 3,661 ft2. The average annual property tax for Villa View Park is $12,002.52. It is located in Orange County.	Median Price: $820,000
Village Green Village Green is a single-family home community in Winter Park, Florida, built in 1972. It currently has no homes for sale. The homes range in size from 1,607 ft2 to 1,958 ft2. The average annual property tax for Village Green is $3,025.93. It is located in Seminole County.
Villas of Casselberry Villas of Casselberry offers a serene retreat with an array of modern amenities designed for comfortable and convenient living. Residents enjoy access to a refreshing community pool perfect for leisurely swims or sunbathing, alongside a scenic pier extending over a tranquil pond ideal for fishing or quiet reflection. Pet owners appreciate the dedicated dog park, where furry companions can romp and socialize freely, while eco-conscious drivers benefit from convenient EV charging stations. Additional perks include a well-equipped fitness center for staying active, a business center for remote work needs, and ample storage units for extra belongings. Controlled access gates ensure peace of mind, complemented by on-site laundry facilities, playground areas for children, and lush green spaces that invite outdoor gatherings and walks. With its blend of recreational and practical features, Villas of Casselberry embodies effortless Florida lifestyle charm. Villas of Casselberry is a townhouse and single-family home community in Winter Park, Florida, built between 1981 and 1994. It currently has 1 single family home for sale with a list price of $389,900. The homes range in size from 996 ft2 to 1,755 ft2. The HOA fees range from $17 to $152 per month. The average annual property tax for Villas of Casselberry is $2,175.86. It is located in Seminole County.	Median Price: $270,000
Virginia Heights Virginia Heights, a picturesque and historic neighborhood, enchants residents with its serene, tree-lined streets and proximity to the shimmering shores of Lake Virginia, offering stunning scenic views that invite leisurely lakeside strolls and peaceful reflection. Renowned for its exceptional walkability, the area seamlessly connects to the vibrant heart of Park Avenue, where charming boutiques, upscale restaurants, and cultural hotspots abound, fostering a lively yet relaxed lifestyle. Dog-friendly parks and abundant green spaces provide ample opportunities for outdoor pursuits like walking, biking, and gardening, while the strong sense of community thrives through local events, volunteer initiatives, and a welcoming atmosphere that celebrates historic charm alongside modern conveniences. Quiet and neighborly, Virginia Heights embodies the quintessential Florida retreat, blending natural beauty with easy access to wine tastings, live music venues, and the area's renowned recreational offerings. Virginia Heights is a single-family home and townhouse community in Winter Park, Florida, built between 1920 and 2024. It currently has 4 single family homes for sale with an average list price of $2,999,750, 1 townhouse for sale with a list price of $845,000, and 1 lot for sale with a list price of $1,690,000. The homes range in size from 823 ft2 to 5,681 ft2. The HOA fees range from $8 to $500 per month. The average annual property tax for Virginia Heights is $9,706.01. It is located in Orange County.	Median Price: $1,450,000
Vistas at Lake Howell Vistas at Lake Howell stands out as a gated community offering an idyllic blend of tranquility and convenience, with stunning lake views that invite residents to unwind amid nature's beauty. This well-manicured enclave boasts essential amenities designed for effortless living, including a refreshing swimming pool, a relaxing spa, and a fully equipped fitness center to keep wellness routines invigorating. Security features provide peace of mind around the clock, while beautifully landscaped grounds and common areas enhance the inviting atmosphere. Beyond the gates, the neighborhood's walkable layout fosters a strong sense of community, with nearby parks, top-rated schools, diverse dining options, and shopping destinations like Casselberry Commons just moments away, making it a haven for those seeking both relaxation and vibrant local access. Vistas at Lake Howell is a townhouse community in Winter Park, Florida, built between 2003 and 2005. It currently has 3 townhouses for sale with an average list price of $346,666.67. The homes range in size from 1,550 ft2 to 1,682 ft2. The HOA fees range from $135 to $175 per month. The average annual property tax for Vistas at Lake Howell is $2,586.90. It is located in Orange County.	Median Price: $350,000
Waterbridge Waterbridge is a single-family home and townhouse community in Winter Park, Florida, built between 1979 and 1985. It currently has no homes for sale. The homes range in size from 1,312 ft2 to 4,961 ft2. The HOA fees range from $40 to $46 per month. The average annual property tax for Waterbridge is $7,103.44. It is located in Orange County.	Median Price: $1,400,000
Waterfall Cove Waterfall Cove offers a serene residential retreat just minutes from the vibrant heart of downtown, blending suburban tranquility with urban accessibility. Residents relish a host of inviting community amenities, including a spacious pool area with lounge chairs for leisurely dips and sunbathing, a dedicated playground for family fun, and a picturesque gazebo perfect for gatherings or quiet reflection. The cove fosters a sense of connection among neighbors through local parks and casual community events. Surrounded by lush Florida landscapes, it's an ideal haven for those seeking the perfect balance of relaxation, recreation, and proximity to shopping, dining, and cultural hotspots. Waterfall Cove is a condo community in Winter Park, Florida, built in 1966. It currently has 7 condos for sale with an average list price of $156,841.43. The homes range in size from 638 ft2 to 1,149 ft2. The HOA fees range from $228 to $572 per month. The average annual property tax for Waterfall Cove is $1,311.30. It is located in Orange County.	Median Price: $130,000
Waters Edge at Hawks Crest Waters Edge at Hawks Crest is a single-family home community in the Hawks Crest neighborhood of Winter Park, Florida, built between 2019 and 2021 by Meritage Homes. It currently has 2 single family homes for sale with an average list price of $1,130,000. The homes range in size from 2,702 ft2 to 4,468 ft2. The HOA fees range from $170 to $243 per month. The average annual property tax for Waters Edge at Hawks Crest is $6,243.76. It is located in Seminole County.	Median Price: $1,160,000
Whispering Waters Whispering Waters is a charming mid-century modern condominium complex perched on the shores of Lake Osceola and offering residents a serene lakeside lifestyle just two blocks from the vibrant shops, restaurants, and cultural attractions of Park Avenue. It features one- and two-bedroom units ranging from studios to spacious 2,300-square-foot residences, many boasting floor-to-ceiling windows, private balconies with stunning lake views, gourmet kitchens, and lushly landscaped grounds. Key amenities include a community pool and sundeck for relaxation, a clubhouse and recreation center for social gatherings, on-site laundry facilities, elevators for convenient access, underground parking with deeded spaces, a private boat dock for water enthusiasts, a secluded courtyard for quiet outdoor enjoyment, and a comprehensive mail and package delivery system, all while maintenance-free living covers essentials like utilities, insurance, and upkeep of common areas to ensure hassle-free luxury. Whispering Waters is an active adult 55+ condo community in Winter Park, Florida, built in 1960. It currently has 4 condos for sale with an average list price of $354,225. The homes range in size from 482 ft2 to 2,350 ft2. The HOA fees range from $649 to $1,373 per month. The average annual property tax for Whispering Waters is $5,351.44. It is located in Orange County.	Median Price: $362,500
Whisperwood Whisperwood is a condo and townhouse community in Winter Park, Florida, built between 1974 and 2012. It currently has 1 townhouse for sale with a list price of $249,900 and 2 condos for sale with an average list price of $160,500. The homes range in size from 756 ft2 to 1,611 ft2. The HOA fees range from $207 to $550 per month. The average annual property tax for Whisperwood is $1,867.93. It is located in Orange County.	Median Price: $155,000
Willa Grove Willa Grove is a single-family home community in Winter Park, Florida, built between 1984 and 1989. It currently has 1 single family home for sale with a list price of $470,000. The homes range in size from 1,603 ft2 to 2,313 ft2. The average annual property tax for Willa Grove is $2,883.87. It is located in Seminole County.	Median Price: $375,000
Williamsburg Williamsburg is a single-family home community in Winter Park, Florida, built between 1966 and 1969. It currently has no homes for sale. The homes range in size from 1,904 ft2 to 2,256 ft2. The average annual property tax for Williamsburg is $4,147.13. It is located in Orange County.	Median Price: $688,500
Windsong Windsong is a single-family home community in Winter Park, Florida, built between 2001 and 2016. It currently has 1 single family home for sale with a list price of $1,525,000. The homes range in size from 2,755 ft2 to 5,196 ft2. The HOA fees range from $235 to $262 per month. The average annual property tax for Windsong is $12,360.67. It is located in Orange County.	Median Price: $1,850,000
Windward Square Windward Square is a townhouse community in Winter Park, Florida, built between 1975 and 1980. It currently has 2 townhouses for sale with an average list price of $322,450. The homes range in size from 849 ft2 to 1,803 ft2. The HOA fees range from $72 to $98 per month. The average annual property tax for Windward Square is $1,888.73. It is located in Seminole County.	Median Price: $270,000
Winflor Court Winflor Court is a single-family home community in Winter Park, Florida, built between 1954 and 2022. It currently has no homes for sale. The homes range in size from 2,188 ft2 to 4,487 ft2. The average annual property tax for Winflor Court is $9,314.29. It is located in Orange County.
Winter Green Winter Green is a townhouse and single-family home community in Winter Park, Florida, built between 1981 and 1995. It currently has 1 townhouse for sale with a list price of $319,900. The homes range in size from 1,090 ft2 to 1,652 ft2. The HOA fees range from $160 to $208 per month. The average annual property tax for Winter Green is $2,156.27. It is located in Seminole County.	Median Price: $284,900
Winter Park Estates Winter Park Estates is a single-family home community in Winter Park, Florida, built between 1957 and 2007. It currently has 7 single family homes for sale with an average list price of $452,814.29. The homes range in size from 1,050 ft2 to 3,156 ft2. The HOA fees range from $2 to $32 per month. The average annual property tax for Winter Park Estates is $3,026.97. It is located in Orange County.	Median Price: $433,750
Winter Park Forest Winter Park Forest is a single-family home community in Winter Park, Florida, built between 1968 and 1969. It currently has no homes for sale. The homes range in size from 1,738 ft2 to 2,187 ft2. The average annual property tax for Winter Park Forest is $1,686.13. It is located in Orange County.
Winter Park Gardens Residents revel in a host of inviting amenities designed to foster relaxation and connection, including a sparkling outdoor pool perfect for leisurely swims on sunny afternoons, a welcoming clubhouse ideal for hosting social events and neighborhood gatherings, and a state-of-the-art fitness center to keep wellness routines vibrant. Meandering walking trails and lighted pathways invite daily strolls amid lush, manicured landscapes, while a tranquil central pond offers peaceful spots for contemplation, complete with garden seating areas that enhance the natural beauty of the surroundings. This thoughtfully curated enclave provides an idyllic retreat for those seeking both community spirit and quiet respite in one of Florida's most picturesque locales. Winter Park Gardens is a condo community in Winter Park, Florida, built in 1964. It currently has 4 condos for sale with an average list price of $239,700. The homes range in size from 512 ft2 to 1,448 ft2. The HOA fees range from $255 to $657 per month. The average annual property tax for Winter Park Gardens is $1,839.54. It is located in Orange County.	Median Price: $250,000
Winter Park Heights Winter Park Heights is a single-family home community in Winter Park, Florida, built between 1965 and 2025. It currently has 2 single family homes for sale with an average list price of $2,147,500. The homes range in size from 1,288 ft2 to 4,041 ft2. The average annual property tax for Winter Park Heights is $10,088.23. It is located in Orange County.	Median Price: $1,850,000
Winter Park Manor Winter Park Manor is a single-family home community in Winter Park, Florida, built between 1959 and 1960. It currently has no homes for sale. The homes range in size from 980 ft2 to 1,769 ft2. The average annual property tax for Winter Park Manor is $2,669.42. It is located in Orange County.	Median Price: $375,000
Winter Park Oaks Winter Park Oaks is a single-family home community in Winter Park, Florida, built between 1994 and 1996. It currently has no homes for sale. The homes range in size from 1,088 ft2 to 1,456 ft2. The average annual property tax for Winter Park Oaks is $1,653.11. It is located in Orange County.	Median Price: $328,000
Winter Park Pines Winter Park Pines is a single-family home community in Winter Park, Florida, built between 1962 and 2023. It currently has 14 single family homes for sale with an average list price of $517,900 and 1 townhouse for sale with a list price of $320,000. The homes range in size from 1,196 ft2 to 3,155 ft2. The HOA fees range from $4 to $82 per month. The average annual property tax for Winter Park Pines is $3,811.56. It is located in Orange County.	Median Price: $528,750
Winter Park Pines Condominiums Winter Park Pines Condominiums is a condo and townhouse community in Winter Park, Florida, built in 1986. It currently has no homes for sale. The homes range in size from 1,043 ft2 to 1,374 ft2. The HOA fees range from $295 to $414 per month. The average annual property tax for Winter Park Pines Condominiums is $1,589.27. It is located in Orange County.	Median Price: $270,000
Winter Park Village Winter Park Village is a single-family home community in Winter Park, Florida, built between 1956 and 2025. It currently has 2 single family homes for sale with an average list price of $1,722,500. The homes range in size from 690 ft2 to 4,638 ft2. The average annual property tax for Winter Park Village is $4,954.82. It is located in Orange County.	Median Price: $520,000
Winter Park Villas Winter Park Villas offers a serene retreat enveloped by lush landscapes and Spanish moss-draped canopies. This inviting community boasts an array of thoughtful amenities designed for relaxation and recreation, including a sparkling swimming pool for leisurely laps, tennis courts for friendly matches, and a fitness center equipped with treadmills and weights to keep residents energized. Families and pet owners alike appreciate the playground, basketball court, and private backyards that foster outdoor play and companionship, while the on-site car wash and outdoor grills provide convenient touches for everyday living. Winter Park Villas is a condo community in Winter Park, Florida, built in 1981. It currently has 1 townhouse for sale with a list price of $199,000 and 7 condos for sale with an average list price of $214,400. The homes range in size from 759 ft2 to 1,350 ft2. The HOA fees range from $264 to $469 per month. The average annual property tax for Winter Park Villas is $1,829.25. It is located in Orange County.	Median Price: $215,000
Winter Park Woods Winter Park Woods offers a serene suburban retreat enveloped by mature trees and lush greenery, ideal for those seeking tranquility amid the vibrant energy of Central Florida. This welcoming community boasts an array of thoughtful amenities designed to enhance everyday living, including a refreshing swimming pool for leisurely swims, tennis courts for friendly matches, and a state-of-the-art fitness center to keep residents active. Families and pet owners alike appreciate the dedicated playground, community clubhouse for social gatherings, and pet-friendly policies that foster a sense of belonging. Outdoor enthusiasts can fire up the BBQ grills for casual cookouts or unwind on private balconies and patios, while on-site laundry facilities and reclaimed water irrigation add practical convenience. Just steps away from local shops, cafes, and restaurants, along with easy access to major highways and nearby universities like Full Sail and the University of Central Florida, Winter Park Woods seamlessly blends relaxation with urban accessibility. Winter Park Woods is a condo community in Winter Park, Florida, built in 1974. It currently has 8 condos for sale with an average list price of $113,112.50. The homes range in size from 130 ft2 to 1,300 ft2. The HOA fees range from $182 to $3,373 per month. The average annual property tax for Winter Park Woods is $969.29. It is located in Orange County.	Median Price: $85,000
Winter Woods Winter Woods is a single-family home community in Winter Park, Florida, built between 1968 and 1973. It currently has 2 single family homes for sale with an average list price of $497,500. The homes range in size from 1,430 ft2 to 2,633 ft2. The HOA fees range from $1 to $25 per month. The average annual property tax for Winter Woods is $2,464.39. It is located in Seminole County.	Median Price: $450,000
Woodcrest Woodcrest is a single-family home community in Winter Park, Florida, built between 1969 and 1982. It currently has 3 single family homes for sale with an average list price of $341,500. The homes range in size from 955 ft2 to 2,700 ft2. The average annual property tax for Woodcrest is $2,110.80. It is located in Seminole County.	Median Price: $416,000
Woodmere Terrace Woodmere Terrace is a single-family home community in Winter Park, Florida, built between 1948 and 2010. It currently has no homes for sale. The homes range in size from 2,800 ft2 to 4,839 ft2. The average annual property tax for Woodmere Terrace is $14,585.31. It is located in Orange County.	Median Price: $3,537,500
Wrenwood Wrenwood is a single-family home community in Winter Park, Florida, built between 1977 and 2023. It currently has 3 single family homes for sale with an average list price of $420,300. The homes range in size from 1,235 ft2 to 2,156 ft2. The HOA fees range from $252 to $252 per month. The average annual property tax for Wrenwood is $2,491.50. It is located in Seminole County.	Median Price: $397,000
Wrenwood Condominiums Wrenwood Condominiums offers a serene retreat with an array of resident-focused amenities designed for relaxed living. At the heart of the community is a sparkling community pool, perfect for leisurely swims or soaking up the Florida sun, complemented by a cozy clubhouse for social gatherings and events. Residents enjoy hassle-free living with comprehensive services including full lawn care, exterior maintenance, and essential utilities like water, sewer, and garbage collection covered by the association. Wrenwood Condominiums is a condo and townhouse community in Winter Park, Florida, built in 1973. It currently has 1 townhouse for sale with a list price of $205,000 and 2 condos for sale with an average list price of $184,950. The homes range in size from 747 ft2 to 1,345 ft2. The HOA fees range from $192 to $441 per month. The average annual property tax for Wrenwood Condominiums is $1,415.61. It is located in Orange County.	Median Price: $191,000
Wrenwood Heights Wrenwood Heights is a single-family home community in Winter Park, Florida, built between 1972 and 1977. It currently has 2 single family homes for sale with an average list price of $399,950. The homes range in size from 1,104 ft2 to 2,282 ft2. The average annual property tax for Wrenwood Heights is $2,394.89. It is located in Orange County.	Median Price: $415,000

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