Top Communities in Cypresswood Country Club, Winter Haven, FL
We have calculated the top communities in Cypresswood Country Club based on the median sale prices of homes. The Cypresswood Country Club community with the highest average home sale price was Cypresswood Plantations with an average of $422,250. All the Cypresswood Country Club communities are listed below with links to view the homes for sale in the communities.
| Cypresswood Plantations | |
| Cypresswood Enclave | |
| Cypresswood Meadows | |
| Cypresswood Garden | |
| Cypresswood Golf Villas | |
| Eagle Pond Condominiums |
All Subdivisions/Condo Buildings in Cypresswood Country Club
| Community | Median Price |
|---|---|
Country Club TrailsCountry Club Trails is a single-family home community in Winter Haven, Florida, built between 2006 and 2015. It currently has 3 single family homes for sale with an average list price of $328,133.33. The homes range in size from 1,113 ft2 to 2,084 ft2. The HOA fees range from $27 to $31 per month. The average annual property tax for Country Club Trails is $2,439.29. It is located in Polk County. |
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Cypress PondCypress Pond is a serene enclave of condominiums and villas offering 2 to 3 bedrooms, open-concept layouts, walk-in closets, interior laundry, and private patios with tranquil pond views, perfect for those seeking low-maintenance living amid lush natural scenery. Residents relish exclusive access to the community's upscale amenities, including an 18-hole championship golf course designed by Ron Garl with practice facilities and a pro shop, a junior Olympic-sized swimming pool, six lighted tennis courts, a wellness center for fitness, a clubhouse with event spaces, a full-service restaurant and lounge, as well as scenic walking paths that enhance the active, resort-like lifestyle. With 24-hour guarded entry and proximity to Central Florida's attractions like Legoland and Orlando, Cypress Pond blends peaceful pondside retreats with vibrant recreational opportunities in this established master-planned haven. Cypress Pond is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1987 and 1989. It currently has 1 single family home for sale with a list price of $255,000. The homes range in size from 1,281 ft2 to 1,697 ft2. The HOA fees range from $27 to $125 per month. The average annual property tax for Cypress Pond is $1,259.16. It is located in Polk County. |
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Cypresswood EnclaveResidents of the Enclave have full access to the community's exceptional amenities, including an 18-hole championship golf course designed by Ron Garl with driving range, putting green, and pro shop, a junior Olympic-sized swimming pool with poolside service, lighted tennis courts, a wellness center for fitness, a grand clubhouse with lounge, full-service restaurant, and bar hosting social events, as well as 24-hour guarded security and scenic walking paths that enhance the resort-like lifestyle. Conveniently located in Central Florida, just minutes from Lake District shopping, dining, and attractions like Legoland and Disney, Cypresswood Enclave blends peaceful residential charm with vibrant, active pursuits in a secure, golf-centric haven. Cypresswood Enclave is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1995 and 2001. It currently has 2 single family homes for sale with an average list price of $253,700. The homes range in size from 1,270 ft2 to 2,370 ft2. The HOA fees range from $105 to $429 per month. The average annual property tax for Cypresswood Enclave is $2,004.95. It is located in Polk County. |
$260,000 |
Cypresswood GardenResidents of Cypresswood Garden have seamless access to the community's array of upscale amenities, including an 18-hole championship golf course designed by Ron Garl with a pro shop and practice facilities, a junior Olympic-sized swimming pool, six lighted tennis courts, a state-of-the-art wellness center for fitness classes, a vibrant clubhouse featuring a full-service restaurant, lounge, and event spaces, as well as scenic walking paths and organized social activities that promote an engaging, resort-like lifestyle. Cypresswood Garden is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1977 and 1979. It currently has 4 single family homes for sale with an average list price of $262,475. The homes range in size from 1,181 ft2 to 2,289 ft2. The HOA fees range from $10 to $129 per month. The average annual property tax for Cypresswood Garden is $1,876.11. It is located in Polk County. |
$256,000 |
Cypresswood Golf VillasCypresswood Golf Villas offer an inviting collection of attached villas and patio homes designed for low-maintenance living, featuring spacious 2- to 3-bedroom layouts with open floor plans, modern updates, and proximity to lush greens and serene lakes, perfect for retirees, seasonal residents, or golf enthusiasts seeking a relaxed yet upscale community lifestyle. As part of this gated, 24-hour guarded enclave, residents enjoy exclusive access to a wealth of amenities, including an acclaimed 18-hole championship golf course designed by Ron Garl, a clubhouse with dining rooms, lounge, and bar, a resort-style swimming pool, tennis courts, a pro shop, wellness center, and golf practice facilities, all fostering a vibrant social scene amid Central Florida's natural beauty. Conveniently located near US Highway 27 for easy access to Orlando and Tampa, Cypresswood Golf Villas blend tranquility with convenience, earning accolades as Winter Haven's top golf destination for an active, community-oriented haven. Cypresswood Golf Villas is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1981 and 1990. It currently has 7 single family homes for sale with an average list price of $220,342.86. The homes range in size from 1,039 ft2 to 1,724 ft2. The HOA fees range from $126 to $290 per month. The average annual property tax for Cypresswood Golf Villas is $1,617.19. It is located in Polk County. |
$214,000 |
Cypresswood MeadowsResidents have seamless access to the community's premier amenities, including an 18-hole championship golf course with pro shop and practice facilities, a junior Olympic-sized swimming pool, six lighted tennis courts with upcoming pickleball additions, a fitness center and wellness gym, a clubhouse featuring a full-service restaurant and bar for social events, as well as scenic walking paths and exclusive member discounts that enhance daily recreation and connectivity. With 24-hour guarded entry ensuring security and proximity to US Highway 27, Legoland, and Orlando's attractions just 45 miles away, Cypresswood Meadows blends tranquil neighborhood living with vibrant, active pursuits in a master-planned haven voted for its top-tier golf experience. Cypresswood Meadows is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1985 and 1993. It currently has 2 single family homes for sale with an average list price of $279,500. The homes range in size from 988 ft2 to 2,343 ft2. The HOA fees range from $22 to $144 per month. The average annual property tax for Cypresswood Meadows is $2,004.12. It is located in Polk County. |
$258,750 |
Cypresswood Palma CeiaResidents revel in the club's array of upscale amenities, including an 18-hole championship golf course designed by Ron Garl with a pro shop and practice facilities, a junior Olympic-sized swimming pool, lighted tennis courts, a state-of-the-art fitness center, a clubhouse featuring dining rooms and a lounge for social events, scenic walking and biking trails, and 24-hour manned security that ensures a secure, vibrant community atmosphere. Conveniently positioned near major attractions like Legoland and just a short drive from Orlando, Palma Ceia blends serene estate living with resort-style conveniences for year-round or seasonal enjoyment. Cypresswood Palma Ceia is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 2005 and 2025. It currently has 1 single family home for sale with a list price of $785,000. The homes range in size from 2,415 ft2 to 2,727 ft2. The HOA fees range from $47 to $147 per month. The average annual property tax for Cypresswood Palma Ceia is $3,488.37. It is located in Polk County. |
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Cypresswood PlantationsNestled within the prestigious Cypresswood Golf & Country Club master-planned community, Cypresswood Plantations is a serene residential neighborhood featuring a mix of single-family homes, villas, and patio-style residences, many with scenic golf course or preserve views, offering 2 to 4 bedrooms and modern upgrades for comfortable living. As part of this gated enclave with over 1,000 homes across multiple sub-neighborhoods, residents of Cypresswood Plantations benefit from an array of upscale amenities, including an 18-hole championship golf course designed by Ron Garl with a pro shop and practice facilities, a Junior Olympic-sized swimming pool, six lighted tennis courts, a clubhouse with a restaurant and bar, playgrounds, and wellness options for an active, resort-style lifestyle. Conveniently located near local attractions like Legoland and with 24-hour guarded access, Cypresswood Plantations provides a secure, family-friendly haven in the heart of Central Florida, just a short drive from Orlando and Tampa. Cypresswood Plantations is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1981 and 2023. It currently has 3 single family homes for sale with an average list price of $522,333.33 and 1 lot for sale with a list price of $150,000. The homes range in size from 1,666 ft2 to 4,584 ft2. The HOA fees range from $18 to $138 per month. The average annual property tax for Cypresswood Plantations is $3,131.25. It is located in Polk County. |
$422,250 |
Cypresswood Sand Hill LaneCypresswood Sand Hill Lane is a serene enclave of single-family homes offering spacious layouts with 3 to 4 bedrooms, split floor plans, and stunning golf course views from many lots, providing an ideal retreat for families, retirees, or golf aficionados seeking privacy and elegance in a master-planned community. Residents revel in the club's array of upscale amenities, including an 18-hole championship golf course designed by Ron Garl with a pro shop, driving range, and short game area; a junior Olympic-sized swimming pool; six lighted tennis courts; a state-of-the-art wellness center for fitness; a vibrant clubhouse featuring a full-service restaurant, pub lounge, and live music events; as well as walking paths and social gatherings that enhance the active, resort-like lifestyle. With 24-hour security and easy access to Central Florida's attractions like Legoland and Orlando, just minutes from Highway 27, this exclusive neighborhood blends tranquil living with endless recreational opportunities in a lush, 600-acre haven voted best golf course in Winter Haven. Cypresswood Sand Hill Lane is a single-family home community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1998 and 2007. It currently has no homes for sale. The homes range in size from 1,949 ft2 to 3,412 ft2. The HOA fees range from $39 to $123 per month. The average annual property tax for Cypresswood Sand Hill Lane is $3,486.15. It is located in Polk County. |
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Eagle Pond CondominiumsEagle Pond Condominiums offers cozy 2-bedroom, 2-bath units with open floor plans, high ceilings, walk-in closets, interior laundry, and serene pond views, providing a low-maintenance haven for retirees, snowbirds, or those seeking resort-style living in Central Florida. Residents benefit from 24-hour guarded security and access to an array of upscale amenities, including an 18-hole championship golf course designed by Ron Garl with practice facilities and pro shop, a junior Olympic-sized swimming pool, six lighted tennis courts, a fitness center, a clubhouse with event spaces, a full-service restaurant and bar, recreation facilities, walking paths, and community events that promote an active, social lifestyle. Conveniently positioned off Highway 27, Eagle Pond provides easy commutes to downtown Winter Haven, Lakeland, and Orlando attractions like Legoland, blending peaceful condominium living with the excitement of nearby shopping, dining, and entertainment. Eagle Pond Condominiums is a condo community in the Cypresswood Country Club neighborhood of Winter Haven, Florida, built between 1999 and 2010. It currently has 4 condos for sale with an average list price of $186,244.25. The homes range in size from 1,017 ft2 to 1,025 ft2. The HOA fees range from $162 to $355 per month. The average annual property tax for Eagle Pond Condominiums is $1,423.36. It is located in Polk County. |
$160,000 |
Lucerne Park ReserveLucerne Park Reserve is a single-family home community in Winter Haven, Florida, built between 2020 and 2022 by D.R. Horton, Dream Finders Homes, and Meritage Homes. It currently has 13 single family homes for sale with an average list price of $300,036. The homes range in size from 1,400 ft2 to 2,696 ft2. The HOA fees range from $1 to $200 per month. The average annual property tax for Lucerne Park Reserve is $4,051.15. It is located in Polk County. |
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