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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36 Photos 919 Avenue S Winter Haven, FL 33880

919 Avenue S
Winter Haven, FL 33880
Almeda Park
Residential

MLS# P4936785 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1751 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Almeda Park

Welcome to 991 S SE in Winter Haven. This beautifully upgraded, turnkey home is being offered fully furnished and sits quietly at the end of a peac... 

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$350,000
Reduced -$24,900
Provided courtesy of EXP REALTY LLC
57 Photos 961 Drexel Avenue Winter Haven, FL 33881

961 Drexel Avenue
Winter Haven, FL 33881
Anna Mar
Residential

MLS# L4959592 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1856 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Anna Mar

***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-story home in Winter Haven is full of character and charm, lo... 

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$315,000
Reduced -$5,000
Provided courtesy of KELLER WILLIAMS REALTY SMART
21 Photos 1726 Upland Lane Winter Haven, FL 33884

1726 Upland Lane
Winter Haven, FL 33884
Ashton Covey
Residential

MLS# W7885114 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2797 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ashton Covey

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfect... 

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$386,990
Provided courtesy of MALTBIE REALTY GROUP
19 Photos 1739 Upland Lane Winter Haven, FL 33884

1739 Upland Lane
Winter Haven, FL 33884
Ashton Covey
Residential

MLS# W7885115 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1815 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ashton Covey

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfect... 

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$326,990
Provided courtesy of MALTBIE REALTY GROUP
17 Photos 1742 Upland Lane Winter Haven, FL 33884

1742 Upland Lane
Winter Haven, FL 33884
Ashton Covey
Residential

MLS# W7885110 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2250 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ashton Covey

Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfect... 

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$380,990
Provided courtesy of MALTBIE REALTY GROUP
39 Photos 5445 Chandler Drive Winter Haven, FL 33884

5445 Chandler Drive
Winter Haven, FL 33884
Bentley Place
Residential

MLS# S5146003 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3010 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Bentley Place

Welcome to 5445 Chandler in Winter Havena great opportunity for buyers looking to add their own personal touch! This home offers generous square fo... 

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$314,500
Reduced -$5,000
Provided courtesy of TRANSCEND REALTY
37 Photos 221 Avenue F Winter Haven, FL 33880

221 Avenue F
Winter Haven, FL 33880
Berry J B Sub
Residential

MLS# L4960995 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 804 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Berry J B Sub

Back on market! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete w... 

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$185,000
Reduced -$15,000
Provided courtesy of HARPER REALTY FL, LLC
17 Photos 307 Sterling Drive Winter Haven, FL 33884

307 Sterling Drive
Winter Haven, FL 33884
Berryhill
Residential

MLS# S5150673 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1444 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Berryhill

Short Sale. Short Sale. Looking for a nice home with amazing potential and opportunity to gain equity? This one may be IT for you! Welcome to this ... 

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$260,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE III
34 Photos 2207 Avenue F Winter Haven, FL 33880

2207 Avenue F
Winter Haven, FL 33880
Beymer Stoner Sub
Residential

MLS# TB8513310 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1310 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Beymer Stoner Sub

Charming and well-maintained home in Winter Haven featuring gorgeous wood flooring throughout the main living areas and porcelain ceramic tile in t... 

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$255,000
Provided courtesy of SOUTHERN PINE REALTY GROUP, LLC
31 Photos 3426 Hickory Street Winter Haven, FL 33881

3426 Hickory Street
Winter Haven, FL 33881
Biltmore Shores
Residential

MLS# O6398170 / Active
3 Beds, 1.00 Total Baths, 1 Full Bath, 1044 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Biltmore Shores

One or more photo(s) has been virtually staged. NO HOA! LOW TAXES! ASSUMABLE FHA LOAN! NEW FLOORS! NEW FENCE! Bring your boat, your work vehicle an... 

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$220,000
Reduced -$10,000
Provided courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

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 06-05-2026 7:58 PM EST.

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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