Pool Homes for Sale Winter Haven FL


Winter Haven FL Real Estate with Pool listings are included below. These homes for sale in Winter Haven Florida with 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 Tour" or "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 1-10 of 91
21 Photos 146 Lake Ring Drive Winter Haven, FL 33884

146 Lake Ring Drive
Winter Haven, FL 33884
Lake Ring
Residential

MLS# TB8517445 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1638 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ring

Welcome to your own slice of paradise! Set on a picturesque lot with serene water views, this stunning pool home offers the lifestyle buyers dream ... 

More Details

$382,999
Provided courtesy of EXP REALTY LLC
26 Photos 423 Majestic Gardens Blvd Winter Haven, FL 33880

423 Majestic Gardens Blvd
Winter Haven, FL 33880
Gardens Ph 01
Residential

MLS# TB8508845 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1941 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Gardens Ph 01

Welcome to this spacious home Located in the gated community of The Gardens, this spacious 4-bedroom, 2-bath home offers an open layout designed fo... 

More Details

$319,500
Reduced -$5,500
Provided courtesy of ORCHARD BROKERAGE, LLC
58 Photos 83 Jenni Ashley Court Winter Haven, FL 33884

83 Jenni Ashley Court
Winter Haven, FL 33884
Skidmore
Residential

MLS# TB8506932 / Active
4 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3799 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Skidmore

Winter Haven, FL is known as the Chain of Lakes City, and this home is located in a beautiful gated subdivision (Skidmore) that sits on Lake Eloise... 

More Details

$875,000
Reduced -$24,000
Provided courtesy of LISTED SIMPLY
28 Photos Winter Haven, FL 33881


Winter Haven, FL 33881
Lake View Sub
Residential

MLS# TB8497837 / Active
2 Beds, 1.00 Total Baths, 1 Full Bath, 2142 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lake View Sub

Fixer upper! THIS COULD BE THE ONE. PRIVATE POOL! So many possibilities! Lovely vaulted ceilings, 2 fireplaces, open kitchen, lovely wood accents, ... 

More Details

$285,900
Provided courtesy of YELLOWFIN REALTY
25 Photos 1151 Carefree Cove Drive Winter Haven, FL 33881

1151 Carefree Cove Drive
Winter Haven, FL 33881
Carefree Cove
Residential

MLS# TB8450979 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1734 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Carefree Cove

Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter H... 

More Details

$425,000
Reduced -$10,000
Provided courtesy of HOMECOIN.COM
9 Photos 119 Allen Avenue Winter Haven, FL 33880

119 Allen Avenue
Winter Haven, FL 33880
Jan Phyl Village
Residential

MLS# TB8399712 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1520 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Jan Phyl Village

Short Sale. Requires a some TLC & Refresh. Pool Home. 

More Details

$250,000
Reduced -$20,000
Provided courtesy of WESTBAY REAL ESTATE
59 Photos 3097 Buckeye Pointe Drive Winter Haven, FL 33881

3097 Buckeye Pointe Drive
Winter Haven, FL 33881
Buckeye Pointe
Residential

MLS# S5150948 / Active
5 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2577 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Buckeye Pointe

Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buy... 

More Details

$449,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
17 Photos 307 Sterling Drive Winter Haven, FL 33884

307 Sterling Drive
Winter Haven, FL 33884
Berryhill
Residential

MLS# S5150673 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1444 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Berryhill

Short Sale. 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 ... 

More Details

$260,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE III
37 Photos Winter Haven, FL 33884


Winter Haven, FL 33884
Elbert Hills
Residential

MLS# S5150298 / Active
5 Beds, 6.00 Total Baths, 5 Full Bath, 1 Half Bath, 3778 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Elbert Hills

Lakefront Opportunity on Lake Elbert! This spacious 5-bedroom, 5.5-bath home sits on a large corner lot with a pool and offers endless potential fo... 

More Details

$499,000
Provided courtesy of LPT REALTY, LLC
67 Photos 815 Lake Jessie Drive Winter Haven, FL 33881

815 Lake Jessie Drive
Winter Haven, FL 33881
East View Pkwy
Residential

MLS# S5149974 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 4128 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: East View Pkwy

Discover this unique Spanish/Mediterranean-inspired estate on an oversized lot across from Lake Jessie on the Chain of Lakes. Featuring a 3BR/2BA m... 

More Details

$620,000
Reduced -$30,000
Provided courtesy of META ONE REALTY GROUP LLC

Broker Reciprocity The information being provided by © 2026 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 is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, 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 06-16-2026 2:00 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 Pools, visit our website daily.

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