David Shippey
863.521.4517

Swimming Pool Homes for Sale in Winter Haven FL


Winter Haven FL Real Estate with Swimming Pool listings are included below. These homes for sale in Winter Haven Florida with Swimming Pools 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 pool 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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Displaying results 1-10 of 97
12 Photos 333 Lake Howard Drive UNIT 204C Winter Haven, FL 33880

333 Lake Howard Drive UNIT 204C
Winter Haven, FL 33880
Imperial Harboursphases 01 & 02
Residential

MLS# U8249519 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1330 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Imperial Harboursphases 01 & 02

Short Sale. BANK APPROVED PRICE! Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious ... 

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$110,000
Reduced -$5,000
Provided courtesy of REALTY COOPERATIVE
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
38 Photos 70 Arthur Lane Winter Haven, FL 33880

70 Arthur Lane
Winter Haven, FL 33880
Not In Subdivision
Residential

MLS# TB8406512 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2460 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Not In Subdivision

Welcome to 70 Arthur Lane a rare opportunity in Winter Haven offering privacy, space, and multi-use flexibility on 3.5 fully fenced acres with no H... 

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$699,999
Provided courtesy of PEOPLE'S TRUST REALTY
27 Photos 3333 Costello Circle Winter Haven, FL 33884

3333 Costello Circle
Winter Haven, FL 33884
Villamar Ph 5
Residential

MLS# TB8387999 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1516 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Villamar Ph 5

Experience Florida living at its finest in this beautifully designed home, perfectly situated on a premium lot with breathtaking views of not one, ... 

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$350,000
Provided courtesy of MARK SPAIN REAL ESTATE
36 Photos 728 Waterbridge Drive Winter Haven, FL 33880

728 Waterbridge Drive
Winter Haven, FL 33880
Whisper Lake 03
Residential

MLS# TB8386118 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 1320 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Whisper Lake 03

This house comes with a REDUCED RATE as low as 5.99% (APR 6.233%) as of 06/12/2025 through List & Lock. This is a seller paid rate-buydown that red... 

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$259,999
Provided courtesy of LIVE FLORIDA REALTY
27 Photos 220 Escambia Drive Winter Haven, FL 33884

220 Escambia Drive
Winter Haven, FL 33884
Eloise Woods Lake Mariam Unit
Residential

MLS# TB8382515 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1701 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods Lake Mariam Unit

Enjoy $5,000 Toward Your Closing CostsCourtesy of the Sellers! This beautifully renovated 3-bedroom, 2-bathroom home is located in a quiet, friendl... 

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$345,000
Provided courtesy of MARK SPAIN REAL ESTATE
59 Photos 53 Paine Drive Winter Haven, FL 33884

53 Paine Drive
Winter Haven, FL 33884
Fla Highlands Co Sub
Residential

MLS# TB8374833 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1788 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Fla Highlands Co Sub

PRICE REDUCED! Come take a look at this beautiful pool home in Garden Grove. Located in the desirable SE Winter Haven and only 5 minutes from LegoL... 

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$330,000
Provided courtesy of KELLER WILLIAMS TAMPA CENTRAL
62 Photos 417 Ruby Lake Place Winter Haven, FL 33884

417 Ruby Lake Place
Winter Haven, FL 33884
Ruby Lake Ph 5
Residential

MLS# TB8357163 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1976 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ruby Lake Ph 5

Welcome to your dream home in the prestigious gated community of Ruby Lakewhere upscale amenities meet a prime location! Conveniently nestled betwe... 

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$409,000
Reduced -$5,000
Provided courtesy of QUICKSILVER REAL ESTATE GROUP
34 Photos 307 Sterling Drive Winter Haven, FL 33884

307 Sterling Drive
Winter Haven, FL 33884
Berryhill
Residential

MLS# S5131074 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1444 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Berryhill

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 3-bedroom, 2... 

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$260,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE III
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

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