Cypresswood Homes For Sale
Welcome to Cypresswood located in Winter Haven FL. The community has a homeowner's association. The amenities include a community swimming pool, golf course, tennis courts, clubhouse, full time security guard and restaurant. The homes for sale in Cypresswood are updated every day from the local MLS. If you would like to schedule a showing or have any questions about any of these homes for sale, please call David Shippey at 863-521-4517 or just click the "More Info" button on any property detail page.
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4050 Palma Ceia Circle
Winter Haven, FL 33884
Cypresswood Palma Ceia
Residential
MLS# O6420265 / Active
Virtually Staged. Brand New 2026 Custom Farmhouse Blends Modern Luxury with Exceptional Craftsmanship. Welcome to 4050 Palma Ceia Circle, a stunni...
440 Palma Ceia Road
Winter Haven, FL 33884
Cypresswood Golf & Country Club
Residential
MLS# O6415193 / Active
Over 1 Acre with Golf Course Views in Cypresswood Golf & Country Club. Discover a rare opportunity to own one of the LARGEST residential lots in Cy...
Reduced -$25,000
2964 Plantation Road
Winter Haven, FL 33884
Cypresswood Plantations
Residential
MLS# O6352519 / Active
Welcome to this refined sanctuary where timeless elegance meets Floridas tranquil landscape. On a premium golf-adjacent lot within the guarded, gat...
Reduced -$20,000
41 Greenfield Court
Winter Haven, FL 33884
Cypresswood
Residential
MLS# L4963295 / Active
Premier Location overlooking the pond and the golf course. This traditional 3 bedroom 2 bath estate home offers split bedrooms, formal living and ...
241 Greenfield Road
Winter Haven, FL 33884
Cypresswood
Residential
MLS# L4959462 / Active
Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot ...
Reduced -$10,000
419 Greenfield Road
Winter Haven, FL 33884
Cypresswood Mdws
Residential
MLS# TB8513442 / Active
Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, b...
Reduced -$2,000
731 Canberra Road
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential
MLS# L4957294 / Active
Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winte...
Reduced -$10,000
2817 Wingfoot Court
Winter Haven, FL 33884
Cypresswood Golf Villas Gc-2
Residential
MLS# P4935798 / Active
Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the ...
29 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential
MLS# L4959890 / Active
New to the market is this ""one owner"" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE W...
Reduced -$10,000
664 Clubhouse Road
Winter Haven, FL 33884
Cypresswood Villas/green Bldg
Residential
MLS# P4939078 / Active
Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and b...
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MLS IDX data last updated on 07-10-2026 5:52 PM EST.