Winter Haven FL Homes for Sale

Winter Haven FL Real Estate listings are included below. These homes for sale in Winter Haven Florida are updated every day from the Central Florida MLS. If you have any questions about any of these Winter Haven Florida homes for sale, just click the "Request More Information" button on any property detail page. We'd love to answer any questions you have, and can provide the past sales history, tax information, and comparable sales for any listing. Let our team of professionals work for you!

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Displaying results 91-100 of 758
62 Photos 1012 Medinah Dr Winter Haven, FL 33884

1012 Medinah Dr
Winter Haven, FL 33884
Cypresswood
Residential

MLS# P4936101 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1458 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. W... 

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$187,900
Reduced -$11,600
Provided courtesy of CROSBY & ASSOCIATES, INC.
31 Photos 14 Enclave Drive Winter Haven, FL 33884

14 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential

MLS# P4935733 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1368 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 01

Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after ""Enclave"" neigh... 

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$229,900
Reduced -$10,000
Provided courtesy of LOCKHART & ASSOCIATES INC
33 Photos 10 Enclave Drive Winter Haven, FL 33884

10 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential

MLS# P4938719 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1368 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 01

WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2... 

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$234,000
Provided courtesy of COLDWELL BANKER REALTY
32 Photos 29 Enclave Drive Winter Haven, FL 33884

29 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential

MLS# L4959890 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1526 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 01

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... 

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$259,900
Reduced -$10,000
Provided courtesy of LOCKHART & ASSOCIATES INC
50 Photos 69 Enclave Drive Winter Haven, FL 33884

69 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 02
Residential

MLS# S5148089 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1682 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 02

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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$300,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
61 Photos 47 Enclave Drive Winter Haven, FL 33884

47 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 2
Residential

MLS# P4937867 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1444 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 2

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... 

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$245,000
Reduced -$15,000
Provided courtesy of XCELLENCE REALTY, INC
24 Photos 688 Augusta Road Winter Haven, FL 33884

688 Augusta Road
Winter Haven, FL 33884
Cypresswood Fairway Patio Homes
Residential

MLS# P4937966 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1586 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Fairway Patio Homes

Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Cou... 

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$337,000
Increase +$17,100
Provided courtesy of JOHN WOOD REALTY, INC.
35 Photos 649 Broadmoor Circle Winter Haven, FL 33884

649 Broadmoor Circle
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential

MLS# O6352259 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1278 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas

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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$149,700
Reduced -$1,800
Provided courtesy of SUCCESS INVESTMENT REALTY
39 Photos 2817 Wingfoot Court Winter Haven, FL 33884

2817 Wingfoot Court
Winter Haven, FL 33884
Cypresswood Golf Villas Gc-2
Residential

MLS# P4935798 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1666 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas Gc-2

Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the ... 

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$270,000
Provided courtesy of NEXTHOME NORRIS & COMPANY REALTY
24 Photos 2270 Firestone Place Winter Haven, FL 33884

2270 Firestone Place
Winter Haven, FL 33884
Cypresswood Golf Villas Gi-4
Residential

MLS# TB8440562 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1439 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas Gi-4

Welcome to this spacious and well-maintained villa in Cypresswood Golf and Country Club, offering comfortable living in one of Winter Havens establ... 

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$185,000
Reduced -$15,000
Provided courtesy of COMPASS FLORIDA LLC

Broker Reciprocity The information being provided by © 2026 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 06-11-2026 8:46 AM EST.

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The Winter Haven Florida Real Estate listings included above are brought to you by David Shippey. 863-521-4517

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