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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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...
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
306 Eagle Pond Drive
Winter Haven, FL 33884
Eagle Pond Condo
Residential
MLS# TB8509154 / Active
Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring througho...
683 Broadmoor Circle UNIT #683
Winter Haven, FL 33884
Cypresswood
Residential
MLS# P4933896 / Active
This villa has recently had upgrades added and the seller is offering $7,000 AT CLOSING TOWARD CLOSING COSTS OR ADDITIONAL UPGRADES. New HVAC syste...
Reduced -$17,000
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
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
704 Eagle Pond Drive UNIT #704
Winter Haven, FL 33884
Eagle Pond Condo
Residential
MLS# P4938866 / Active
Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood G...
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...
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MLS IDX data last updated on 07-10-2026 7:53 PM EST.