Most Affordable Condo Communities in Winter Park, FL

We have calculated the most affordable condo buildings/communities in Winter Park based on the median sale prices of homes. The Winter Park condo buildings/communities with the lowest average home sale price was Winter Park Woods with an average of $85,000. All the Winter Park condo buildings are listed below with links to view the homes for sale in the buildings.

Winter Park Woods
$85,000
Colonies
$97,500
Waterfall Cove
$130,000
Golfside Villas
$140,000
Whisperwood
$155,000
The Stratford
$157,750
Four Seasons
$170,000
Lancelot at Winter Park
$170,000
Hidden Oaks
$175,000
Parkview Village
$185,000

Least Expensive Condos for Sale in Winter Park

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Condo Communities in Winter Park

Community Median Price

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

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

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 $298,880. 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

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

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: 97,500

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 4 condos for sale with an average list price of $213,475. 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 $1,629.06. It is located in Orange County.
Median Price: 170,000

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

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 3 condos for sale with an average list price of $248,266.67. The homes range in size from 1,068 ft2 to 1,230 ft2. The HOA fees range from $231 to $310 per month. The average annual property tax for Goldenrod Villas is $1,764.98. It is located in Seminole County.
Median Price: 262,500

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

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 $209,979.60 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

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

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: 382,500

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 6 condos for sale with an average list price of $315,333.17. 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 $1,993.35. It is located in Orange County.
Median Price: 260,000

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

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 $181,712.86. 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 $171,525. 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

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

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

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

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

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

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: 1,131,000

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: 718,500

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

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

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 3 single family homes for sale with an average list price of $2,891,333.33, 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: 312,500

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

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 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

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: 277,000

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: 255,000

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 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 6 condos for sale with an average list price of $223,800. 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: 216,500

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 7 condos for sale with an average list price of $112,128.57. 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

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
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