Winter Haven Florida Homes for Sale

Winter Haven Florida Real Estate listings are included below. The Homes for sale in Winter Haven Florida are updated every day from the Central Florida MLS. If you would like to search more specifically in Winter Haven, scroll down the page to Specialty Searches such as 55+ Homes, Pool Homes, Golf Homes, Luxury Homes, Historic Homes, No HOA Homes, and Waterfront Homes. If you have any questions about any of these Winter Haven Florida homes for sale, just click the "More Info" button on any property detail page.

Winter Haven is known for its 26 connecting lakes which are called the "Chain of Lakes". These lakes are great for boating, fishing & water skiing. It is also home to Legoland which offers a theme park & water park based around Lego themes.

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Displaying results 91-100 of 761
43 Photos 241 Greenfield Road Winter Haven, FL 33884

241 Greenfield Road
Winter Haven, FL 33884
Cypresswood
Residential

MLS# L4959462 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 2523 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot ... 

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$359,950
Reduced -$10,000
Provided courtesy of PORCHLIGHT HOMES LLC
46 Photos 683 Broadmoor Circle UNIT #683 Winter Haven, FL 33884

683 Broadmoor Circle UNIT #683
Winter Haven, FL 33884
Cypresswood
Residential

MLS# P4933896 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1139 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

NEW, NEW, NEW...this villa has recently been renovated. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. ... 

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$198,000
Reduced -$17,000
Provided courtesy of BHHS FLORIDA PROPERTIES GROUP
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

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Specific Searches of Winter Haven Florida

55 Plus Homes For Sale Winter Haven FL
Golf Homes For Sale Winter Haven FL
Historic Homes For Sale Winter Haven FL
Luxury Homes For Sale Winter Haven FL
No HOA Homes For Sale Winter Haven FL
Pool Homes For Sale Winter Haven FL
Waterfront Homes For Sale Winter Haven FL