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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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
14 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential
MLS# P4935733 / Active
This meticulously maintained and professionally updated 2 bedroom 2 bath villa is located in the sought after ""Enclave"" neighborhood in Cypresswo...
Reduced -$10,000
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...
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
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...
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...
Reduced -$4,100
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
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
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 ...
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MLS IDX data last updated on 07-10-2026 7:53 PM EST.