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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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
318 Greenfield Road
Winter Haven, FL 33884
Cypresswood
Residential
MLS# L4961904 / Active
Nestled on a beautifully landscaped and tree shaded lot this well maintained 3 bedroom 2 bathroom home features split bedrooms with ample closets, ...
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
1039 Medinah Drive
Winter Haven, FL 33884
Cypresswood
Residential
MLS# P4938088 / Active
1 OWNER HOME!! Don't miss out on this 2 bed 2 bath tennis villa in the highly desired neighborhood of Cypresswood. The HOA takes care of the roof, ...
Reduced -$4,000
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
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
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
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
10 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential
MLS# P4938719 / Active
WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2...
69 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 02
Residential
MLS# S5148089 / Active
Welcome to 69 Enclave Drive, a beautifully updated home nestled inside the sought-after Cypresswood Golf & Country Club, a gated golf community kno...
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MLS IDX data last updated on 06-06-2026 2:00 AM EST.