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 our local MLS. If you would like to schedule a showing or have any questions about any of these Winter Haven FL homes for sale, please call 863-521-4517 or just click the "Schedule a Showing" or "Request More Info" button on any property detail pages.

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27 Photos 415 Smiley Court Winter Haven, FL 33884

415 Smiley Court
Winter Haven, FL 33884
Lake Mariam Hills Rep
Residential

MLS# S5128812 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2420 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Mariam Hills Rep

3 spacious bedrooms + 1 versatile study/office??? Large great room with excellent natural light??? Open kitchen integrated into the dining room, id... 

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$440,000
Reduced -$10,000
Provided courtesy of AGENT TRUST REALTY CORPORATION
53 Photos 1905 Emily Boulevard Winter Haven, FL 33884

1905 Emily Boulevard
Winter Haven, FL 33884
Emily Estates
Residential

MLS# O6320123 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3050 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Emily Estates

Welcome to your new dream home! This spacious 4-bedroom, 3.1-bathroom gem spans over 3,000 square feet, offering ample room for comfort and creativ... 

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$350,000
Reduced -$10,000
Provided courtesy of ELITE REALTY, 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
86 Photos 550 Lake Otis Drive Winter Haven, FL 33880

550 Lake Otis Drive
Winter Haven, FL 33880
Mayfair Sub
Residential

MLS# S5128104 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 6232 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Mayfair Sub

NEW PRICE! AVAILABLE! NOW IS YOUR CHANCE TO OWN THIS LEEDY MID CENTURY MODERN LAKEFRONT HOME with a POOL! Unique opportunity to own a custom design... 

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$929,000
Reduced -$70,000
Provided courtesy of HAPPY DAYS REALTY LLC
29 Photos 97 Parson Drive Winter Haven, FL 33884

97 Parson Drive
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential

MLS# TB8392094 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 989 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

Looking for a highly sought after 55+ community in Winter Haven with NO LOT RENT? Well look no further! Become a shareholder in one of the most pop... 

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$89,500
Reduced -$5,400
Provided courtesy of JT REALTY & ASSOCIATES
1 Photos 916 25th Street Winter Haven, FL 33881

916 25th Street
Winter Haven, FL 33881
Inwood
Residential

MLS# P4933332 / Active
3 Beds, 1.00 Total Baths, 1 Full Bath, 1266 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Inwood

Short Sale. SHORT SALE!! SHORT SALE!! Seller accepting CASH ONLY!! Needs TLC. Bankruptcy short sale will take about 120 days to get response on off... 

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$150,000
Increase +$30,000
Provided courtesy of CROSBY & ASSOCIATES, INC.
26 Photos 32 Berna Circle Winter Haven, FL 33884

32 Berna Circle
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential

MLS# P4933983 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1274 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

This is a meticulously maintained 2 bedroom/2 bathroom home nestled in highly sought after 55+ community of Orange Manor West. Located in Southeast... 

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$135,000
Provided courtesy of TOWN & COUNTRY REAL ESTATE
57 Photos 3614 Plymouth Drive Winter Haven, FL 33884

3614 Plymouth Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# P4935794 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2109 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Located in the premier active adult gated community of Traditions at Lake Ruby, this exceptional home sits on a premium lot with picturesque pond v... 

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$339,000
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES
1 Photos 2502 Sage Valley Way Winter Haven, FL 33884

2502 Sage Valley Way
Winter Haven, FL 33884
Harmony At Lake Eloise
Residential

MLS# O6250897 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2773 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Harmony At Lake Eloise

Under Construction. Find everything you need in Harmony on Lake Eloise! Located just minutes from world class theme parks and attractions, Harmony ... 

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$413,105
Reduced -$3,000
Provided courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
36 Photos 3942 Warbler Drive Winter Haven, FL 33880

3942 Warbler Drive
Winter Haven, FL 33880
Queens Cove Ph 04
Residential

MLS# L4952485 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1555 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Queens Cove Ph 04

Welcome to your move-in-ready dream home! This charming 3-bedroom, 2-bathroom split-family residence features a spacious living room serves as the ... 

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$260,000
Provided courtesy of KELLER WILLIAMS REALTY SMART

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 08-12-2025 2:02 AM EST.

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The Winter Haven homes above are brought to you by David Shippey REALTOR®.


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