Cypresswood Country Club, Winter Haven, FL, Real Estate

Cypresswood Golf & Country Club is a gated, master-planned community offering a serene yet vibrant lifestyle centered around its premier golfing facilities and family-friendly environment. Residents enjoy an array of top-tier amenities, including an 18-hole championship golf course designed by Ron Garl, complete with a pro shop and practice facilities, a junior Olympic-sized swimming pool, six lighted tennis courts, and a modern wellness center for fitness enthusiasts. The community clubhouse serves as a social hub, featuring a full-service restaurant and bar, event spaces for gatherings, and organized community activities. Surrounded by scenic walking paths and lush landscapes, Cypresswood provides 24-hour guarded access, ensuring privacy and security, while its central Florida location offers easy access to nearby shopping, dining, and attractions like Legoland and Orlando.

Cypresswood Country Club currently has 37 single family homes for sale with an average list price of $301,010.54, 4 condos for sale with an average list price of $186,244.25, and 1 lot for sale with a list price of $150,000. The average annual property tax for Cypresswood Country Club is $2,105.56.

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Subdivisions

Subdivisions Median Price
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Cypress Pond

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. Cypress 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. ... Read more
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Cypresswood Enclave

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. Residents 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. ... Read more
Median Price: $260,000
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Cypresswood Garden

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. Residents 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. ... Read more
Median Price: $256,000
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Cypresswood Golf Villas

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. Cypresswood 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. ... Read more
Median Price: $230,000
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Cypresswood Meadows

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. Residents 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. ... Read more
Median Price: $245,250
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Real Estate News

New Homes For Sale This Week in Cypresswood Country Club: November 14th to November 20th

New Homes For Sale This Week in Cypresswood Country Club: November 14th to November 20th - November 21, 2025

Cypresswood Country Club had 2 new homes for sale during the week of Friday, November 14 to Thursday, November 20, including including 2 single family homes for sale with an ... continue reading
Homes Just Sold in Cypresswood Country Club: November 11th to November 17th

Homes Just Sold in Cypresswood Country Club: November 11th to November 17th - November 18, 2025

Cypresswood Country Club had only 1 sale during the week of Tuesday, November 11 to Monday, November 17, including and it was a condo for sale with a list price ... continue reading
Homes Just Sold in Cypresswood Country Club: November 4th to November 10th

Homes Just Sold in Cypresswood Country Club: November 4th to November 10th - November 11, 2025

Cypresswood Country Club had only 1 sale during the week of Tuesday, November 4 to Monday, November 10, including and it was a condo for sale with a list price ... continue reading
New Homes For Sale This Week in Cypresswood Country Club: October 24th to October 30th

New Homes For Sale This Week in Cypresswood Country Club: October 24th to October 30th - October 31, 2025

Cypresswood Country Club had 2 new homes for sale during the week of Friday, October 24 to Thursday, October 30, including including 2 single family homes for sale with an ... continue reading
New Homes For Sale This Week in Cypresswood Country Club: October 17th to October 23rd

New Homes For Sale This Week in Cypresswood Country Club: October 17th to October 23rd - October 24, 2025

Cypresswood Country Club had 2 new homes for sale during the week of Friday, October 17 to Thursday, October 23, including including 2 single family homes for sale with an ... continue reading
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