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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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
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
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 ...
419 Greenfield Road
Winter Haven, FL 33884
Cypresswood Mdws
Residential
MLS# TB8513442 / Active
Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, b...
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
665 Broadmoor Circle
Winter Haven, FL 33884
Cypresswood Tennis Villas
Residential
MLS# TB8496998 / Active
Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully...
Reduced -$10,000
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...
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...
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MLS IDX data last updated on 06-06-2026 2:00 AM EST.