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.

Click Here to Create a Free Profile to Gain Access to Detailed MLS Information that only real estate agents have access to. Your Free Profile also enables you to save your favorite search's and homes.

Modify Search Criteria

Displaying results 31-40 of 97
64 Photos 2683 Wyndsor Oaks Way Winter Haven, FL 33884

2683 Wyndsor Oaks Way
Winter Haven, FL 33884
Wyndsor At Lake Winterset
Residential

MLS# P4933374 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3440 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Wyndsor At Lake Winterset

Welcome to 2683 Wyndsor Oaks Way, Winter Haven, FL - an extraordinary residence in the highly sought-after gated Wyndsor at Lake Winterset communit... 

More Details

$849,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
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... 

More Details

$549,900
Reduced -$40,100
Provided courtesy of REAL BROKER, LLC
44 Photos 4201 Shadow Wood Drive Winter Haven, FL 33880

4201 Shadow Wood Drive
Winter Haven, FL 33880
Shadow Wood
Residential

MLS# B4901791 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1860 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Shadow Wood

Short Sale. This POOL home is ready for new owners! This house features beautiful quartz countertops and new cabinets throughout the kitchen and bo... 

More Details

$385,000
Provided courtesy of FREEDOM REALTY
34 Photos 148 Lake Otis Road Winter Haven, FL 33884

148 Lake Otis Road
Winter Haven, FL 33884
Lakewood
Residential

MLS# P4933622 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2663 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lakewood

Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level hom... 

More Details

$482,000
Provided courtesy of LOCKHART & ASSOCIATES INC
40 Photos 1500 8th Street Winter Haven, FL 33880

1500 8th Street
Winter Haven, FL 33880
Highland Estates
Residential

MLS# S5111772 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2617 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Highland Estates

Beautiful Renovated 3Bed/2Bath Pool Home with 2,617 square feet of living area, this home boasts a spacious floor plan with oversized rooms and a d... 

More Details

$379,990
Reduced -$10,010
Provided courtesy of PREFERRED REAL ESTATE BROKERS
28 Photos 1002 Lake Elbert Drive Winter Haven, FL 33880

1002 Lake Elbert Drive
Winter Haven, FL 33880
Coker A B Sub
Residential

MLS# O6303365 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2844 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Coker A B Sub

LAKE/POOL HOME with 160' of Lake Elbert Frontage! This beautiful brick residence offers resort-style living right at your doorstep with a private s... 

More Details

$849,900
Provided courtesy of EPIQUE REALTY, INC.
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... 

More Details

$1,350,000
Provided courtesy of THE K TEAM REAL ESTATE SERVICES LLC
56 Photos
Open House: Sun Jul 20th, 11:00am - 1:00pm
1006 W Lake Hamilton Drive Winter Haven, FL 33881

1006 W Lake Hamilton Drive
Winter Haven, FL 33881
Pollard Shores
Residential

MLS# P4933594 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3068 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Pollard Shores

PRICE REDUCED! Stunning three-bedroom, two-and-a-half-bath home on .97 acres with breathtaking views of Lake Hamilton. This beautifully designed re... 

More Details

$855,000
Reduced -$10,000
Provided courtesy of LOCKHART & ASSOCIATES INC
76 Photos
Open House: Sun Jul 20th, 1:00pm - 4:00pm
934 Lake Elbert Drive Winter Haven, FL 33880

934 Lake Elbert Drive
Winter Haven, FL 33880
El Otis Park Sub
Residential

MLS# L4952236 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 3198 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: El Otis Park Sub

Welcome to a one-of-a-kind lakeside retreat in the heart of Winter Haven a beautifully preserved 1926 residence set on over half an acre of direct ... 

More Details

$499,000
Reduced -$13,000
Provided courtesy of KELLER WILLIAMS REALTY SMART
55 Photos
Open House: Sun Jul 20th, 11:00am - 2:00pm
4812 Mandolin Court Winter Haven, FL 33884

4812 Mandolin Court
Winter Haven, FL 33884
Mandolin 02
Residential

MLS# L4954516 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2067 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Mandolin 02

Welcome to this stunning 4-bedroom, 3-bathroom home with a dedicated office and a sparkling inground saltwater pool, nestled in the gated community... 

More Details

$450,000
Provided courtesy of BHHS FLORIDA PROPERTIES GROUP

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 07-21-2025 2:01 AM EST.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions

For a fresh updated list of Homes for sale in Winter Haven with Swimming Pools, visit our website daily.

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


Related Searches

Winter Haven Florida Swimming Pool Homes For Sale.
Winter Haven Florida Homes with Swimming Pools.
Winter Haven FL Pool Houses For Sale.
Winter Haven FL Houses with Swimming Pools.