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 81-90 of 97
9 Photos 6685 Briarhill Dr Ne Winter Haven, FL 33881

6685 Briarhill Dr Ne
Winter Haven, FL 33881
Lake N Golf Estates Add
Residential

MLS# P4935348 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1534 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake N Golf Estates Add

WELCOME TO FLORIDA RETIREMENT LIVING....See this CHARMIMG 2BR 2BA home located in Lake N Golf Estates in beautiful Winter haven !! A MUST SEE is th... 

More Details

$149,900
Provided courtesy of TOWN & COUNTRY REAL ESTATE
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... 

More Details

$260,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE III
76 Photos 125 Lake Roy Drive Winter Haven, FL 33884

125 Lake Roy Drive
Winter Haven, FL 33884
Eloise Woods Lake Roy Unit
Residential

MLS# B4902008 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 1900 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods Lake Roy Unit

Timeless Elegance Meets Modern Comfort on the South Chain of LakesWelcome to your lakeside sanctuary in the heart of Winter Haven. This beautifully... 

More Details

$699,900
Provided courtesy of FREEDOM REALTY
32 Photos 2200 21st Street Winter Haven, FL 33881

2200 21st Street
Winter Haven, FL 33881
Orange Shores
Residential

MLS# L4954254 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1359 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Orange Shores

Tucked away just seconds from Lake Hartridge Nature Park and boat ramp, this charming 3-bedroom, 2-bath home offers the perfect blend of comfort, o... 

More Details

$320,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
59 Photos 5671 Cypress Gardens Road Winter Haven, FL 33884

5671 Cypress Gardens Road
Winter Haven, FL 33884
N/a
Residential

MLS# O6312804 / Active
6 Beds, 6.00 Total Baths, 4 Full Bath, 2 Half Bath, 4335 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: N/a

Experience luxurious lakefront living with unmatched privacy and modern upgrades at 5671 Cypress Gardens Road in Winter Haven, FL. Situated on 4.53... 

More Details

$900,000
Reduced -$50,000
Provided courtesy of EXP REALTY LLC
19 Photos
Open House: Sun Jul 27th, 12:00am - 3:00pm
904 15th Street Winter Haven, FL 33881

904 15th Street
Winter Haven, FL 33881
Lake Elbert Estates
Residential

MLS# O6323490 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 1743 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake Elbert Estates

WELCOME TO YOUR NEXT GEN TURN KEY HOME. This MULTI FAMILY USE home sits in the beautiful town of Winter Haven. Just a few minutes from Lake Elbert,... 

More Details

$390,000
Provided courtesy of LPT REALTY, LLC
67 Photos 200 Island Way Winter Haven, FL 33884

200 Island Way
Winter Haven, FL 33884
Orchid Springs Unrecorded
Residential

MLS# P4935447 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3555 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orchid Springs Unrecorded

Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Esta... 

More Details

$975,000
Provided courtesy of LOCKHART & ASSOCIATES INC
49 Photos 413 Ruby Lake Place Winter Haven, FL 33884

413 Ruby Lake Place
Winter Haven, FL 33884
Ruby Lake Ph 4
Residential

MLS# P4934997 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2172 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ruby Lake Ph 4

Welcome to this beautifully maintained pool home offering comfort, space, and style in a prime location! As you enter the walkway, youll be greeted... 

More Details

$514,000
Reduced -$1,000
Provided courtesy of STACEY TOWNS REALTY LLC
47 Photos 114 Belmont Drive Winter Haven, FL 33884

114 Belmont Drive
Winter Haven, FL 33884
Montego Place
Residential

MLS# P4935006 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2069 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Montego Place

Welcome to this spacious and beautifully designed pool home, perfect for entertaining and family living! As you step through the front door, youre ... 

More Details

$425,000
Reduced -$10,000
Provided courtesy of STACEY TOWNS REALTY LLC
35 Photos 111 Beverly Drive Winter Haven, FL 33884

111 Beverly Drive
Winter Haven, FL 33884
Eloise Woods Lake Roy Unit
Residential

MLS# L4953434 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1977 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Woods Lake Roy Unit

Perfect 4 Bed / 2 Bath Pool Home for entertaining! Dont miss this beautifully maintained 4-bedroom, 2-bath split-plan home featuring the sought-aft... 

More Details

$379,900
Reduced -$20,000
Provided courtesy of REMAX EXPERTS

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 8:37 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.