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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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
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
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
1052 Medinah Drive
Winter Haven, FL 33884
Cypresswood
Residential
Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a cour...
Reduced -$20,000
1 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential
MLS# L4963196 / Active
Opportunity Knocks! Build sweat equity in this 3 bedroom 2 bathroom villa that is ready for some cosmetic updates. Make this home your own with f...
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 ...
649 Broadmoor Circle
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential
MLS# O6352259 / Active
UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throu...
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
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
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...
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MLS IDX data last updated on 07-10-2026 7:53 PM EST.