Homes with Pools for Sale in Osceola County, FL

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ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to Paradise Palms Resort! This beautifully maintained and fully furnished 4-bedroom, 3-bathroom townhome offers the perfect combination of vacation luxury and investment potential. Featuring an open-concept floor plan, a convenient first-floor bedroom, spacious upstairs suites, and a private screened-in heated pool, this home is ready for immediate enjoyment or short-term rental income. The resort-style gated community offers outstanding amenities including a lagoon-style pool, spa, fitness center, movie theater, arcade, clubhouse, sports courts, concierge services, and 24-hour guarded security. HOA fees include cable, internet, landscaping, and exterior maintenance. Ideally located

$338,300

4 beds3 baths1,902 sq ft

2959 Banana Palm Dr, Kissimmee, FL 34747

First-floor bedroom • Lagoon-style pool • Fitness center

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to this exceptional 8-bedroom, 6-bathroom resort home in the highly desirable Windsor at Westside community, where stunning pond views, privacy, and resort-style amenities come together to create the ultimate Central Florida retreat. Offered fully furnished and professionally equipped for short-term rentals, this turnkey property is ready for immediate enjoyment or income generation. Designed to accommodate large families and vacation groups, the spacious floor plan features expansive gathering areas, a modern kitchen with granite countertops and stainless-steel appliances, and two primary suites conveniently located on separate floors. Thoughtfully decorated and well-maintained, th

$629,000

8 beds6 baths4,041 sq ft

1829 Gobi Dr, Kissimmee, FL 34747

Lazy river • Fitness center • Solar panels

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to 1036 Plantation Dr, Unit D8, Kissimmee, FL 34741! This charming 1-bedroom, 1-bathroom condo offers comfortable living with a spacious open floorplan designed for both relaxation and entertaining. The bright living and dining areas flow seamlessly into the kitchen, creating an inviting and functional layout. The generously sized bedroom features a walk-in closet, providing ample storage space. Step outside to enjoy your private balcony, perfect for relaxing with your morning coffee or unwinding at the end of the day. Residents can also enjoy access to the community pool, offering the perfect spot to cool off and relax. Additional upgrades and features include fully replaced A/C du

$139,000

1 bed1 bath734 sq ft

1036 Plantation Dr Unit D8, Kissimmee, FL 34741

Community pool • Walk-in closet • Private balcony

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
ACTIVE REUNION RESORT MEMBERSHIP! Welcome to Reunion Resort and this beautifully maintained 3-bedroom, 2-bathroom condo in Heritage Crossing, offered FULLY FURNISHED and ready to enjoy as a primary residence, vacation home, or turnkey investment property. Featuring granite countertops, updated furnishings, and laminate flooring throughout, no carpet! This move-in-ready unit offers both style and low-maintenance living. Relax on your private balcony overlooking the 12th hole of the Tom Watson-designed Independence Course, providing stunning golf course views. Recent community improvements include a new roof installed in 2024 and a full exterior repaint completed in 2025. The Active Reunion R

$289,000

3 beds2 baths1,344 sq ft

7673 Heritage Crossing Way #102, Reunion, FL 34747

New roof • $650 HOA • Community pool

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to 5033 Caspian St - A beautifully maintained townhome located in the highly sought-after Lakeshore at Narcoossee gated community just south of the booming Lake Nona area! Built in 2019, this move-in ready residence offers an open-concept floor plan designed for comfortable everyday living and effortless entertaining. The spacious living and dining areas flow seamlessly into a beautifully appointed kitchen featuring granite countertops, espresso cabinetry, and a large center island, creating a bright and inviting space for entertaining. Just off the kitchen, a private nook provides the perfect work-from-home area and opens to an expansive private courtyard, ideal for grilling, relax

$314,900

2 beds2.5 baths1,464 sq ft

5033 Caspian St, Saint Cloud, FL 34771

Gated community • Private nook • Fitness center

Property at 441 Spoonbill Ct, Kenansville, FL 34739, 4 beds, 2 baths

$519,000

4 beds2 baths2,310 sq ft

441 Spoonbill Ct, Kenansville, FL 34739

Property at 3045 Beach Palm Ave, Kissimmee, FL 34747, 4 beds, 3 baths

$349,999

4 beds3 baths1,902 sq ft

3045 Beach Palm Ave, Kissimmee, FL 34747

Property at 945 Desert Mountain Ct, Reunion, FL 34747, 5 beds, 5.5 baths

$895,000

5 beds5.5 baths3,319 sq ft

945 Desert Mountain Ct, Reunion, FL 34747

Property at 6658 Syreeta Ln, Harmony, FL 34773, 4 beds, 2 baths

$414,900

4 beds2 baths1,901 sq ft

6658 Syreeta Ln, Harmony, FL 34773

Property at 3607 Main Harbor Dr, Kissimmee, FL 34746, 3 beds, 2.5 baths

$285,000

3 beds2.5 baths1,550 sq ft

3607 Main Harbor Dr, Kissimmee, FL 34746

Property at 374 Ocean Course Ave, Davenport, FL 33896, 4 beds, 3 baths

$380,000

4 beds3 baths1,914 sq ft

374 Ocean Course Ave, Davenport, FL 33896

Property at 1594 Sandbagger Dr, Davenport, FL 33896, 8 beds, 5 baths

$754,000

8 beds5 baths3,909 sq ft

1594 Sandbagger Dr, Davenport, FL 33896

Property at 955 Louvre Ct, Kissimmee, FL 34759, 4 beds, 2 baths

$299,900

4 beds2 baths2,088 sq ft

955 Louvre Ct, Kissimmee, FL 34759

Property at 8904 Sydney Ave, Kissimmee, FL 34747, 5 beds, 4.5 baths

$429,000

5 beds4.5 baths2,263 sq ft

8904 Sydney Ave, Kissimmee, FL 34747

Property at 1420 Moon Vly, Davenport, FL 33896, 9 beds, 5 baths

$650,000

9 beds5 baths3,909 sq ft

1420 Moon Vly, Davenport, FL 33896

Property at 3486 Hawkin Dr, Kissimmee, FL 34746, 3 beds, 2.5 baths

$330,000

3 beds2.5 baths1,833 sq ft

3486 Hawkin Dr, Kissimmee, FL 34746

Property at 7612 Cabana Ct #202, Reunion, FL 34747, 3 beds, 3 baths

$283,500

3 beds3 baths1,630 sq ft

7612 Cabana Ct #202, Reunion, FL 34747

Property at 4018 Waving Hickory Blvd, Saint Cloud, FL 34772, 4 beds, 2.5 baths

$365,900

4 beds2.5 baths2,066 sq ft

4018 Waving Hickory Blvd, Saint Cloud, FL 34772

Property at 1885 Nice Ct, Kissimmee, FL 34747, 6 beds, 4.5 baths

$559,000

6 beds4.5 baths3,142 sq ft

1885 Nice Ct, Kissimmee, FL 34747

Property at 1533 Flange Dr, Davenport, FL 33896, 8 beds, 5 baths

$745,000

8 beds5 baths3,909 sq ft

1533 Flange Dr, Davenport, FL 33896

Property at 2717 Fiesta Key Dr, Kissimmee, FL 34747, 7 beds, 4.5 baths

$599,990

7 beds4.5 baths2,881 sq ft

2717 Fiesta Key Dr, Kissimmee, FL 34747

Property at 8936 Prague Way, Kissimmee, FL 34747, 6 beds, 4.5 baths

$524,900

6 beds4.5 baths3,142 sq ft

8936 Prague Way, Kissimmee, FL 34747

Property at 3115 Tocoa Cir, Kissimmee, FL 34746, 4 beds, 3.5 baths

$450,000

4 beds3.5 baths1,782 sq ft

3115 Tocoa Cir, Kissimmee, FL 34746

Property at 2948 Crest Dr, Kissimmee, FL 34744, 4 beds, 2.5 baths

$445,000

4 beds2.5 baths1,923 sq ft

2948 Crest Dr, Kissimmee, FL 34744

Property at 8137 Roseville Rd, Davenport, FL 33896, 4 beds, 3.5 baths

$349,500

4 beds3.5 baths2,060 sq ft

8137 Roseville Rd, Davenport, FL 33896

Property at 617 Cypress Creek Run, Saint Cloud, FL 34771, 4 beds, 2 baths

$414,905

4 beds2 baths1,819 sq ft

617 Cypress Creek Run, Saint Cloud, FL 34771

Property at 3523 Clay Brick Rd, Harmony, FL 34773, 3 beds, 2.5 baths

$314,900

3 beds2.5 baths1,876 sq ft

3523 Clay Brick Rd, Harmony, FL 34773

Property at 3206 Gold Ln, Kissimmee, FL 34747, 4 beds, 3 baths

$309,900

4 beds3 baths1,694 sq ft

3206 Gold Ln, Kissimmee, FL 34747

Property at 5483 Paradise Cay Cir, Kissimmee, FL 34746, 3 beds, 3 baths

$300,000

3 beds3 baths1,187 sq ft

5483 Paradise Cay Cir, Kissimmee, FL 34746

Property at 1322 Seven Eagles Ct #302, Reunion, FL 34747, 1 bed, 1 bath

$179,000

1 bed1 bath823 sq ft

1322 Seven Eagles Ct #302, Reunion, FL 34747

Property at 6526 Circle Rock Way, Saint Cloud, FL 34771, 4 beds, 3 baths

$599,990

4 beds3 baths2,438 sq ft

6526 Circle Rock Way, Saint Cloud, FL 34771

Property at 3165 Caribbean Soul Dr, Kissimmee, FL 34747, 3 beds, 3 baths

$393,000

3 beds3 baths1,550 sq ft

3165 Caribbean Soul Dr, Kissimmee, FL 34747

Property at 2834 Storey Cove Ave, Kissimmee, FL 34746, 8 beds, 5 baths

$819,000

8 beds5 baths4,289 sq ft

2834 Storey Cove Ave, Kissimmee, FL 34746

Property at 3180 Paradox Cir #405, Kissimmee, FL 34746, 2 beds, 2 baths

$299,000

2 beds2 baths1,196 sq ft

3180 Paradox Cir #405, Kissimmee, FL 34746

Property at 8032 Acadia Estates Ct, Kissimmee, FL 34747, 6 beds, 5.5 baths

$580,000

6 beds5.5 baths2,904 sq ft

8032 Acadia Estates Ct, Kissimmee, FL 34747

Property at 212 Ocean Course Ave, Davenport, FL 33896, 4 beds, 3 baths

$368,000

4 beds3 baths1,914 sq ft

212 Ocean Course Ave, Davenport, FL 33896

Property at 401 Fountainhead Cir #155, Kissimmee, FL 34741, 1 bed, 1 bath

$153,900

1 bed1 bath744 sq ft

401 Fountainhead Cir #155, Kissimmee, FL 34741

Property at 2617 Hammock Harbor Ave, St Cloud, FL 34771, 2 beds, 2 baths

$368,726

2 beds2 baths1,579 sq ft

2617 Hammock Harbor Ave, St Cloud, FL 34771

Property at 2747 N Poinciana Blvd #10, Kissimmee, FL 34746, 3 beds, 2 baths

$199,000

3 beds2 baths1,287 sq ft

2747 N Poinciana Blvd #10, Kissimmee, FL 34746

Property at 9031 Wildflower Ln, Kissimmee, FL 34747, 3 beds, 2.5 baths

$299,000

3 beds2.5 baths1,530 sq ft

9031 Wildflower Ln, Kissimmee, FL 34747

Property at 3013 Bonfire Beach Dr #201, Kissimmee, FL 34746, 3 beds, 2 baths

$295,000

3 beds2 baths1,444 sq ft

3013 Bonfire Beach Dr #201, Kissimmee, FL 34746

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Based on information submitted to the MLS GRID as of Sat Sep 26 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 Osceola County

There are currently 3529 homes with pools for sale in Osceola County at a median listing price of $400K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Osceola County stay on the market for 103 days and receive 1 offers. This map is refreshed with the newest listings in Osceola County every 15 minutes.

In the past month, 700 homes have been sold in Osceola County. In addition to houses in Osceola County, there were also 724 condos, 1252 townhouses, and 21 multi-family units for sale in Osceola County last month. Find your dream home in Osceola County 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 Osceola County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Osceola County. If you're looking to sell your home in the Osceola County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Osceola County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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