David Shippey
863.521.4517

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 1-10 of 826
65 Photos 180 Brigham Road Winter Haven, FL 33881

180 Brigham Road
Winter Haven, FL 33881
Hartridge Harbor Addition
Residential

MLS# O6293503 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3659 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hartridge Harbor Addition

PRICE ADJUSTMENT | NOW OFFERED UNDER APPRAISED VALUE ~ Click on the virtual tour link for a tour of the property. No HOA and conveniently between T... 

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$3,495,000
Reduced -$150,000
Provided courtesy of PREMIER SOTHEBY'S INTL. REALTY
47 Photos 950 N Lake Otis Drive Winter Haven, FL 33880

950 N Lake Otis Drive
Winter Haven, FL 33880
El Otis Park Sub
Residential

MLS# TB8407564 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 5178 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: El Otis Park Sub

There was a time when homes were designed to lastand this is one of them. Designed by award-winning architect Gene Leedy, this south-facing lakefro... 

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$2,600,000
Provided courtesy of COMPASS FLORIDA LLC
100 Photos 3826 Gaines Court Winter Haven, FL 33884

3826 Gaines Court
Winter Haven, FL 33884
Gaines Cove
Residential

MLS# P4934458 / Active
6 Beds, 6.00 Total Baths, 5 Full Bath, 1 Half Bath, 5400 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Gaines Cove

***PRICE REDUCTION*** Amazing Winter Haven Executive Home on 1.86 Acres with Lake Eloise Frontage! Welcome to this elegant two-story home nestled o... 

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$1,999,990
Reduced -$400,009
Provided courtesy of NEW HOME ADVANTAGE LLC
100 Photos 3001 Crystal Beach Road Winter Haven, FL 33880

3001 Crystal Beach Road
Winter Haven, FL 33880
Bingham John A Jr Sub
Residential

MLS# P4933259 / Active
8 Beds, 7.00 Total Baths, 7 Full Bath, 7810 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Bingham John A Jr Sub

Welcome to your dream home at 3001 Crystal Beach Road in Winter Haven, FLa masterpiece of luxury and sophistication. This breathtaking 8-bedroom, 7... 

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$1,490,000
Reduced -$105,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
48 Photos 1441 S Lake Roy Drive Winter Haven, FL 33884

1441 S Lake Roy Drive
Winter Haven, FL 33884
South Roy Shores
Residential

MLS# P4931110 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 4513 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: South Roy Shores

CHAIN OF LAKES!!! POOL!!! 5 BEDROOMS AND 4.5 BATHROOMS!!! This is the listing you have been waiting for - look no further. This incredible residenc... 

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$1,350,000
Provided courtesy of THE K TEAM REAL ESTATE SERVICES LLC
98 Photos 1123 Cypress Point Winter Haven, FL 33884

1123 Cypress Point
Winter Haven, FL 33884
Cypress Point
Residential

MLS# P4934938 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2713 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypress Point

ELEGANT POOL HOME ON CHAIN OF LAKES! Paradise awaits you at this fabulous lakefront residence that offers the ultimate in comfort, space and sunset... 

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$1,300,000
Provided courtesy of COLDWELL BANKER REALTY
63 Photos 2682 Wyndsor Oaks Place Winter Haven, FL 33884

2682 Wyndsor Oaks Place
Winter Haven, FL 33884
Wyndsor At Lake Winterset
Residential

MLS# O6275048 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 4070 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Wyndsor At Lake Winterset

PRICE JUST REDUCED $50,000! With and a new roof from 2023, this home offers its own private, covered, newly updated boathouse with a boat lift prov... 

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$1,250,000
Reduced -$49,000
Provided courtesy of EXP REALTY LLC
65 Photos 250 Brigham Road Winter Haven, FL 33881

250 Brigham Road
Winter Haven, FL 33881
N/a
Residential

MLS# P4934742 / Active
5 Beds, 6.00 Total Baths, 5 Full Bath, 1 Half Bath, 3235 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: N/a

Prepare to be utterly enchanted by this stunning lakefront retreat on Lake Hartridge, perfectly positioned on the coveted Winter Haven Chain of Lak... 

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$1,195,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
81 Photos 121 E Lake Summit Drive Winter Haven, FL 33884

121 E Lake Summit Drive
Winter Haven, FL 33884
Eloise Woods
Residential

MLS# P4931785 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 4591 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods

***The seller agrees to pay off the solar panels at closing.*** Step into a world of lakeside luxury with this majestic red-brick residence, where ... 

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$1,150,000
Reduced -$100,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
79 Photos 1836 Woodpointe Drive Winter Haven, FL 33884

1836 Woodpointe Drive
Winter Haven, FL 33884
Woodpointe Ph 02
Residential

MLS# P4935305 / Active
5 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 4021 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Ph 02

Tucked inside one of Winter Havens most sought-after gated communities, this custom-built lakefront estate on the sparkling, spring-fed Lake Daisy ... 

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$1,050,000
Provided courtesy of JOHN WOOD REALTY, INC.

Broker Reciprocity The information being provided by © 2025 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 REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, 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 07-20-2025 1:45 PM 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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