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
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, ...
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...
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...
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 ...
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
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
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...
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
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MLS IDX data last updated on 06-05-2026 7:58 PM EST.