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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2813 Wingfoot Ct
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential
MLS# L4959887 / Active
Welcome to 2813 Wingfoot Court now one of the best values in Cypresswood Golf & Country Club!Perfectly positioned along the 8th fairway inside this...
Reduced -$15,000
47 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 2
Residential
PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Ho...
Reduced -$15,000
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
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
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...
Reduced -$1,800
1012 Medinah Dr
Winter Haven, FL 33884
Cypresswood
Residential
MLS# P4936101 / Active
NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. W...
Reduced -$11,600
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 ...
14 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential
MLS# P4935733 / Active
Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after ""Enclave"" neigh...
Reduced -$10,000
683 Broadmoor Circle UNIT #683
Winter Haven, FL 33884
Cypresswood
Residential
MLS# P4933896 / Active
NEW, NEW, NEW...this villa has recently been renovated. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. ...
Reduced -$17,000
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MLS IDX data last updated on 06-06-2026 7:27 PM EST.