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 71-80 of 97
69 Photos
Open House: Fri Jul 25th, 4:00pm - 6:00pm
3805 Gaines Drive Winter Haven, FL 33884

3805 Gaines Drive
Winter Haven, FL 33884
Gaines Cove
Residential

MLS# L4952454 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3225 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Gaines Cove

Seller motivated and will review all offers! Welcome to this stunning 4-bedroom, 3-bathroom ranch-style home located in the highly sought-after nei... 

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$599,000
Reduced -$16,000
Provided courtesy of PAIGE WAGNER HOMES REALTY
72 Photos 5200 Pebble Beach Boulevard Winter Haven, FL 33884

5200 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4935325 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2443 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites... 

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$555,000
Provided courtesy of LAKE ASHTON REALTY INC.
46 Photos 3991 Island Lakes Drive Winter Haven, FL 33881

3991 Island Lakes Drive
Winter Haven, FL 33881
Island Lakes
Residential

MLS# S5128469 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2640 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Island Lakes

Welcome to your personal lakeside retreat! This stunning two-story home offers 4 spacious bedrooms, 2.5 bathrooms, and a versatile loft perfect for... 

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$600,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
41 Photos 686 22nd Street Winter Haven, FL 33880

686 22nd Street
Winter Haven, FL 33880
Orangewood Heights
Residential

MLS# L4954036 / Active
5 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2588 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Orangewood Heights

Spacious Pool Home with In-Law Suite in Desirable Orangewood Heights!Welcome to this unique and versatile 5-bedroom, 3.5-bath pool home offering 2,... 

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$344,999
Provided courtesy of LIVE FLORIDA REALTY
39 Photos 1317 Avenue A Winter Haven, FL 33880

1317 Avenue A
Winter Haven, FL 33880
Elbert Hills
Residential

MLS# P4935343 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2194 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Elbert Hills

Welcome to 1317 Avenue A SE in Winter Haven, FL - A truly one-of-a-kind! This 4-bedroom, 3.5-bath home (including an en suite) is overflowing with ... 

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$400,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
31 Photos 560 Saint Andrews Road Winter Haven, FL 33884

560 Saint Andrews Road
Winter Haven, FL 33884
Cypresswood
Residential

MLS# P4934871 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1922 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

Immaculate POOL HOME in CYPRESSWOOD - Fully Renovated & Located in a gated golf community!!!Welcome to your dream home in the highly desirable Cypr... 

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$327,000
Reduced -$12,500
Provided courtesy of BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY
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
62 Photos 1 Brogden Court Winter Haven, FL 33880

1 Brogden Court
Winter Haven, FL 33880
Brogden Point Rep
Residential

MLS# L4952907 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3020 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Brogden Point Rep

Custom-Built by Hulbert Homes! Known for their exceptional quality and craftsmanship, Hulbert Homes delivers again with this thoughtfully designed ... 

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$849,900
Reduced -$25,100
Provided courtesy of EXP REALTY LLC
24 Photos 403 Saint Anns Drive Winter Haven, FL 33884

403 Saint Anns Drive
Winter Haven, FL 33884
Planters Walk Ph 03
Residential

MLS# L4950593 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1596 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Planters Walk Ph 03

WOW!!! $30,000 PRICE ADJUSTMENT!! NEW ROOF to be installed prior to closing at this price! Welcome HOME!! WOW, It is time to get into this Spacious... 

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$287,500
Provided courtesy of KELLER WILLIAMS REALTY SMART
37 Photos 961 Oleander Drive Winter Haven, FL 33880

961 Oleander Drive
Winter Haven, FL 33880
Cooper Estates
Residential

MLS# P4934912 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2030 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Cooper Estates

The property you are inquiring about is located in Winter Haven, FL, in the In-town SE area of Polk County. This is a super convenient location. Th... 

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$325,000
Provided courtesy of BROKERS REALTY OF CENTRAL FLOR

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