Homes with Pools for Sale in Winter Haven, FL

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ABOUT THIS HOME
Home with a Pool for sale in Winter Haven, FL:
Discover this traditional 2-bedroom, 2-bath villa offering a bright, open layout and exceptional pride of ownership throughout. The welcoming foyer with a cozy sitting area leads into a spacious great room and dining area overlooking the enclosed Florida room and serene garden courtyard. The well-appointed kitchen features abundant cabinetry, a closet pantry, and an open design perfect for entertaining. Both bedrooms are generously sized with ample closet space. Home has garage door screen, flagstone patio with tropical plantings, and a roof replaced in 2013/2014. Located in the desirable Park Lake community, residents enjoy a large pool, recreational building, private dock on the renowned

$210,000

2 beds2 baths1,224 sq ft

2206 San Marcos Cir SE, Winter Haven, FL 33880

Open layout • Abundant cabinetry • Closet pantry

OPEN SAT, 11AM TO 2PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Winter Haven, FL:
Welcome to 1020 Lena Run Court, a spacious pool home tucked inside the gated community of Hidden Creek. Designed for comfortable everyday living. This home offers a generous floor plan with inviting living spaces, abundant natural light, and plenty of room to make your own. Step outside to your private screened pool and covered outdoor living area. With no rear neighbors, the backyard offers an added sense of privacy, making it the perfect setting for morning coffee, weekend gatherings, or relaxing in the Florida sunshine. The spacious primary suite provides a comfortable retreat, while additional bedrooms and flexible living areas provide plenty of options for guests including a home offic

$598,000

5 beds3 baths3,068 sq ft

1020 Lena Run Ct, Winter Haven, FL 33880

Gated community • No rear neighbors • Move in ready

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Winter Haven, FL:
Welcome to one of THE MOST DESIRABLE AND BEAUTIFUL 55+ GATED/GUARD community in Winter Haven, FL! LAKE ASHTON has great amenities for their residents to enjoy every day and feel in PARADISE. An enormous club house were events are held, two pools, dog park, golf course, bowling, movie theater, fitness center, restaurant, and more. There's also a 2nd clubhouse available for residents. This gorgeous well maintained home has MULTIPLE VALUABLE UPGRADES that the future owner would enjoy. Even the floor plan was updated in the KITCHEN making this home UNIQUE in the neighborhood! NEW ROOF was installed in 2024, DISHWASHER FEB 2026, REFRIGETATOR NOV 2025, and WATER HEATER 2021. Also ENJOY the BENEF

$364,500

3 beds2 baths1,833 sq ft

5325 Snead Dr, Winter Haven, FL 33884

Gated community • Dog park • Fitness center

NEW 7 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Winter Haven, FL:
Waterfront Living • Renovated Interior • Private Garage. Imagine ending your day with a beautiful Florida sunset over Lake Winterset. This beautifully renovated 2-bedroom, 2-bath condominium offers something that is hard to find in condo living—a private 1-car garage, expansive waterfront views, and the added character of a second-floor residence with vaulted ceilings and skylights. Located in the gated Winterset community, this home combines a relaxed lakefront lifestyle with a thoughtfully updated interior that is comfortable, stylish, and move-in ready. The kitchen is truly the centerpiece, featuring abundant cabinetry, granite countertops, stainless-steel appliances, a s

$235,000

3 beds2 baths1,308 sq ft

809 Magnolia Pl #809, Winter Haven, FL 33884

Wood flooring • Private garage • Updated bathrooms

NEW 7 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Winter Haven, FL:
Discover exceptional Florida living in this fabulous Eco Smart 3-bedroom, 3-bath home with a den, ideally situated in the premier gated active-adult community of Traditions at Lake Ruby. Designed with comfort, efficiency, and entertaining in mind, this beautifully appointed home offers an impressive array of upgrades and thoughtful features. The desirable split-bedroom floor plan provides privacy and versatility, including a spacious Junior Bedroom Suite with its own ensuite bath—perfect for visiting family or guests. The well-equipped kitchen is a chef’s delight, featuring a center island with pendant lighting, fingerprint-resistant stainless-steel appliance package, recessed l

$350,000

3 beds3 baths2,006 sq ft

3541 Raleigh Dr, Winter Haven, FL 33884

Junior bedroom suite • Extended lanai • Walk-in pantry

Property at 822 17th Ter NE, Winter Haven, FL 33881, 4 beds, 2.5 baths

$379,900

4 beds2.5 baths2,189 sq ft

822 17th Ter NE, Winter Haven, FL 33881

Property at 3761 Giorgio Dr, Winter Haven, FL 33884, 4 beds, 2 baths

$329,090

4 beds2 baths1,840 sq ft

3761 Giorgio Dr, Winter Haven, FL 33884

Property at 3921 Giorgio Dr, Winter Haven, FL 33884, 4 beds, 2 baths

$336,970

4 beds2 baths1,840 sq ft

3921 Giorgio Dr, Winter Haven, FL 33884

Property at 628 Pavare Ct #1, Winter Haven, FL 33884, 2 beds, 2 baths

$99,000

2 beds2 baths823 sq ft

628 Pavare Ct #1, Winter Haven, FL 33884

Property at 6183 Grey Heron Dr, Winter Haven, FL 33881, 5 beds, 4 baths

$340,000

5 beds4 baths1,872 sq ft

6183 Grey Heron Dr, Winter Haven, FL 33881

Property at 3087 Captain Jax Way, Winter Haven, FL 33884, 3 beds, 2.5 baths

$224,990

3 beds2.5 baths1,386 sq ft

3087 Captain Jax Way, Winter Haven, FL 33884

Property at 2622 Lasso Loop, Eagle Lake, FL 33839, 5 beds, 3 baths

$323,740

5 beds3 baths2,498 sq ft

2622 Lasso Loop, Eagle Lake, FL 33839

Property at 6204 Knotty Pine Dr SE, Winter Haven, FL 33884, 2 beds, 2 baths

$165,000

2 beds2 baths1,014 sq ft

6204 Knotty Pine Dr SE, Winter Haven, FL 33884

Property at 66 Joppa Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$99,500

2 beds2 baths1,144 sq ft

66 Joppa Dr, Winter Haven, FL 33884

Property at 97 Parson Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$79,500

2 beds2 baths989 sq ft

97 Parson Dr, Winter Haven, FL 33884

Property at 4401 Chambliss Rd, Winter Haven, FL 33884, 3 beds, 2 baths

$1,200,000

3 beds2 baths2,129 sq ft

4401 Chambliss Rd, Winter Haven, FL 33884

Property at 706 Avenue I NE, Winter Haven, FL 33881, 3 beds, 2 baths

$295,000

3 beds2 baths1,925 sq ft

706 Avenue I NE, Winter Haven, FL 33881

Property at 604 Sarner Pass Way, Winter Haven, FL 33881, 4 beds, 2 baths

$338,000

4 beds2 baths2,004 sq ft

604 Sarner Pass Way, Winter Haven, FL 33881

Property at 1711 Garden Lake Dr #1711, Winter Haven, FL 33884, 1 bed, 1 bath

$170,000

1 bed1 bath828 sq ft

1711 Garden Lake Dr #1711, Winter Haven, FL 33884

Property at 6364 Lolly Bay Loop NE, Winter Haven, FL 33881, 2 beds, 2 baths

$215,000

2 beds2 baths1,143 sq ft

6364 Lolly Bay Loop NE, Winter Haven, FL 33881

Property at 2801 Wingfoot Ct, Winter Haven, FL 33884, 2 beds, 2 baths

$249,900

2 beds2 baths1,666 sq ft

2801 Wingfoot Ct, Winter Haven, FL 33884

Property at 304 Corso Loop, Winter Haven, FL 33884, 3 beds, 2 baths

$220,000

3 beds2 baths— sq ft

304 Corso Loop, Winter Haven, FL 33884

(954) 615-2180

Property at 3831 Gaines Dr, Winter Haven, FL 33884, 3 beds, 2 baths

$765,000

3 beds2 baths2,678 sq ft

3831 Gaines Dr, Winter Haven, FL 33884

Property at 6260 Botticella Blvd, Winter Haven, FL 33884, 5 beds, 2.5 baths

$293,990

5 beds2.5 baths2,112 sq ft

6260 Botticella Blvd, Winter Haven, FL 33884

Property at 624 Sarner Pass Way, Winter Haven, FL 33881, 4 beds, 2 baths

$299,000

4 beds2 baths1,617 sq ft

624 Sarner Pass Way, Winter Haven, FL 33881

Property at 815 Andrew St, Winter Haven, FL 33881, 4 beds, 2 baths

$344,990

4 beds2 baths1,814 sq ft

815 Andrew St, Winter Haven, FL 33881

Property at 2590 Lasso Loop, Eagle Lake, FL 33839, 4 beds, 2 baths

$257,740

4 beds2 baths1,600 sq ft

2590 Lasso Loop, Eagle Lake, FL 33839

Property at 2603 Lasso Loop, Eagle Lake, FL 33839, 4 beds, 3 baths

$360,490

4 beds3 baths2,366 sq ft

2603 Lasso Loop, Eagle Lake, FL 33839

Property at 6136 Pebble Beach Blvd, Winter Haven, FL 33884, 3 beds, 3 baths

$549,999

3 beds3 baths2,682 sq ft

6136 Pebble Beach Blvd, Winter Haven, FL 33884

Property at 1776 6th St NW #304, Winter Haven, FL 33881, 2 beds, 2 baths

$106,000

2 beds2 baths1,347 sq ft

1776 6th St NW #304, Winter Haven, FL 33881

Property at 44 Brevard Dr, Winter Haven, FL 33884, 3 beds, 2 baths

$495,500

3 beds2 baths2,269 sq ft

44 Brevard Dr, Winter Haven, FL 33884

Property at 5014 Sunrise Dr, Winter Haven, FL 33880, 4 beds, 3 baths

$399,900

4 beds3 baths2,006 sq ft

5014 Sunrise Dr, Winter Haven, FL 33880

Property at 333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880, 3 beds, 2 baths

$145,000

3 beds2 baths1,226 sq ft

333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880

Property at 350 Winter Ridge Blvd #350, Winter Haven, FL 33881, 2 beds, 2 baths

$152,000

2 beds2 baths1,073 sq ft

350 Winter Ridge Blvd #350, Winter Haven, FL 33881

Property at 2215 Starboard Dr #29, Winter Haven, FL 33881, 2 beds, 2 baths

$184,900

2 beds2 baths1,436 sq ft

2215 Starboard Dr #29, Winter Haven, FL 33881

Property at 6455 Hollyberry Ln NE, Winter Haven, FL 33881, 2 beds, 2 baths

$152,000

2 beds2 baths1,144 sq ft

6455 Hollyberry Ln NE, Winter Haven, FL 33881

Property at 6107 Grand Oaks Dr SE, Winter Haven, FL 33884, 2 beds, 2 baths

$175,000

2 beds2 baths1,340 sq ft

6107 Grand Oaks Dr SE, Winter Haven, FL 33884

Property at 543 Terranova Cir, Winter Haven, FL 33884, 3 beds, 2 baths

$385,000

3 beds2 baths2,118 sq ft

543 Terranova Cir, Winter Haven, FL 33884

Property at 333 Lake Howard Dr NW Unit 302B, Winter Haven, FL 33880, 2 beds, 2 baths

$107,000

2 beds2 baths1,030 sq ft

333 Lake Howard Dr NW Unit 302B, Winter Haven, FL 33880

Property at 6627 Westchester Dr NE, Winter Haven, FL 33881, 2 beds, 2 baths

$198,000

2 beds2 baths1,856 sq ft

6627 Westchester Dr NE, Winter Haven, FL 33881

Property at 120 Lake Mariam Way, Winter Haven, FL 33884, 4 beds, 2.5 baths

$415,000

4 beds2.5 baths2,308 sq ft

120 Lake Mariam Way, Winter Haven, FL 33884

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Based on information submitted to the MLS GRID as of Thu Sep 17 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Winter Haven

There are currently 399 homes with pools for sale in Winter Haven at a median listing price of $294K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Haven stay on the market for 97 days and receive 1 offers. Popular neighborhoods include Rock Springs Ridge, Caribe Cove, Ruby Lake, Lake Ashton, and Downtown Winter Haven. This map is refreshed with the newest listings in Winter Haven every 15 minutes.

In the past month, 101 homes have been sold in Winter Haven. In addition to houses in Winter Haven, there were also 51 condos, 46 townhouses, and 7 multi-family units for sale in Winter Haven last month. Winter Haven is a minimally walkable city in Polk County with a Walk Score of 25. Winter Haven is home to approximately 34,907 people and 22,420 jobs. Find your dream home in Winter Haven using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Haven are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Haven. Our Winter Haven real estate stats and trends will give you more information about home buying and selling trends in Winter Haven. If you're looking to sell your home in the Winter Haven area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Haven with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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