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 31-40 of 97
49 Photos 4225 Shadow Wood Court Winter Haven, FL 33880

4225 Shadow Wood Court
Winter Haven, FL 33880
Shadow Wood
Residential

MLS# L4950216 / Active
5 Beds, 3.00 Total Baths, 3 Full Bath, 3680 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Shadow Wood

No HOA or CDD fees! This expansive 3,600 sq. ft. residence is perfectly designed for a multi generational family with a mother in-law suite! With 5... 

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$639,000
Reduced -$21,000
Provided courtesy of S & D REAL ESTATE SERVICE LLC
89 Photos 255 Lake Link Road Winter Haven, FL 33884

255 Lake Link Road
Winter Haven, FL 33884
Lakewood Add
Residential

MLS# P4934836 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2627 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lakewood Add

Welcome to your dream retreat on the shimmering shores of Lake Link in beautiful Winter Haven, Florida offering a 2-year paid Home Warranty! This s... 

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$625,000
Reduced -$25,000
Provided courtesy of DALTON WADE INC
49 Photos 720 Lake Jessie Drive Winter Haven, FL 33881

720 Lake Jessie Drive
Winter Haven, FL 33881
Lewellen Bay
Residential

MLS# L4950601 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 2982 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lewellen Bay

Welcome to your Winter Haven Chain of Lakes Lakefront home, a stunning 5-bedroom, 4-bathroom estate offering the perfect blend of luxury, privacy, ... 

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$624,990
Reduced -$14,910
Provided courtesy of LA ROSA REALTY PRESTIGE
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
69 Photos 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
32 Photos 952 N Heron Circle Winter Haven, FL 33884

952 N Heron Circle
Winter Haven, FL 33884
Garden Grove South Add
Residential

MLS# P4933451 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3058 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Garden Grove South Add

PRICE REDUCED $61,000!!**Stunning Lakefront Home with Private Views, Pool, and Outdoor Living Spaces - Nestled in a serene lakeside setting, this b... 

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$589,000
Reduced -$10,000
Provided courtesy of DALTON WADE INC
51 Photos 18 Aqualane Drive Winter Haven, FL 33880

18 Aqualane Drive
Winter Haven, FL 33880
Moores Eagle Lake Shores
Residential

MLS# L4953923 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2196 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Moores Eagle Lake Shores

Wake up to breathtaking morning sunrises over Eagle Lake from this stunning waterfront retreat. Tucked away on a peaceful dead-end street, this bea... 

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$579,000
Provided courtesy of BERRY REALTY & APPRAISAL SERVICES PA
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.
74 Photos 1 Lake Eloise Lane Winter Haven, FL 33884

1 Lake Eloise Lane
Winter Haven, FL 33884
Harbour Estates
Residential

MLS# L4951160 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2550 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Harbour Estates

Don't miss out on this amazing 4/3 single-family home with a pool near Lake Eloise in winter Haven! This remarkable home features a newer roof, HVA... 

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$549,900
Provided courtesy of KELLER WILLIAMS REALTY SMART
55 Photos 19 Meadowlake Court Winter Haven, FL 33884

19 Meadowlake Court
Winter Haven, FL 33884
Cypresswood
Residential

MLS# O6279343 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3257 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

New Price Reduction - Priced to Sell! Step into luxury with this stunning ranch-style home in the gated Cypresswood golf community! Nestled on a pe... 

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$549,900
Reduced -$40,100
Provided courtesy of REAL BROKER, LLC

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 3:53 PM EST.

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