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 one of the best-located homes in Windsor at Westside Resort! Situated on a premium corner lot and just steps from the clubhouse, this fully furnished 5-bedroom, 4.5-bathroom townhome offers one of the closest walkable locations to the resort’s incredible amenities, making it especially desirable for vacation guests and short-term rental success. Enjoy easy access to the resort-style pool, lazy river, water slides, hot tub, fitness center, arcade, playground, sports courts, tiki bar, and on-site restaurant. Inside, you’ll find a welcoming foyer with a convenient drop zone leading into a bright, open-concept floor plan. The first floor features tile throughout with no c

$424,900

5 beds4.5 baths2,265 sq ft

2070 Rome Dr, Kissimmee, FL 34747

Lazy river • Water slides • Premium corner lot

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Virtually Staged. Motivated Seller! * * Move-in ready 4 bedroom, 2 bathroom home in the desirable Esprit community with no rear neighbors! * * This well-maintained home features * * brand new luxury vinyl plank flooring (June 2026) * * and a bright open floor plan with a split bedroom layout. * * The standout feature is the custom-built outdoor kitchen, * * complete with a * * wood-fired brick pizza oven, built-in sink, and prep space, * * making it the perfect space for entertaining. The * * screened lanai, fully fenced backyard, and no rear neighbors * * provide privacy and room to enjoy Florida living. Inside, the kitchen offers * * granite countertops, a large islan

$370,000

4 beds2 baths1,859 sq ft

3969 Eternity Cir, Saint Cloud, FL 34772

Community pool • Screened lanai • 7,000 sq ft lot

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Experience luxury resort living in this exceptional 5-bedroom, 5-bath home overlooking the Nicklaus Golf Course in Reunion Resort. Whether you're searching for a primary residence, an unforgettable second home, or a proven vacation rental investment, this property offers the perfect blend of comfort, style, and entertainment. Designed for entertaining, the home features a private pool and spa, expansive sun deck, outdoor kitchen, fire pit, covered dining, and multiple outdoor games. Inside, you'll find a Las Vegas-inspired casino lounge, an impressive arcade and game room, two spacious primary suites, a gourmet kitchen with stainless steel appliances, and beautifully themed bedrooms that cr

$975,000

5 beds5.5 baths3,203 sq ft

824 Desert Mountain Ct, Reunion, FL 34747

Private pool • Spa • Arcade and game room

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to this spacious 3-bedroom, 2-bath second-floor condo in the gated community of Flora Ridge in Kissimmee. Enjoy an open-concept layout where the kitchen, dining, and family room flow together, perfect for everyday living and entertaining. The kitchen offers ample cabinetry, a full appliance package, and a breakfast bar overlooking the great room. The generous primary suite features a walk-in closet and an en-suite bath with dual vanities and a separate glass-enclosed shower. Two additional bedrooms and a full guest bath provide flexible space for family, guests, or a home office. Step out to your private screened balcony and take in tranquil views of the community pond and lush gree

$245,000

3 beds2 baths1,433 sq ft

3001 Laurel Run Ln #206, Kissimmee, FL 34741

Gated community • Ample cabinetry • Walk-in closet

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
TURNKEY 4-BEDROOM POOL HOME NEAR DISNEY! Welcome to this beautifully located 4-bedroom, 3-bath home in desirable Oak Island Cove, Kissimmee. Just minutes from Walt Disney World, Margaritaville, shopping, dining, and Central Florida’s world-famous attractions, this home is an ideal primary residence, vacation home, or second home. The spacious open floor plan features two primary suites, bright living areas, a private screened-in pool, and a converted games room offering additional space for family and entertaining. Fully furnished and move-in ready, the home allows you to enjoy the Florida lifestyle from day one. Roof replaced in 2018. Located in a community that allows short-term ren

$445,900

4 beds3 baths1,662 sq ft

2914 Blooming Alamanda Loop, Kissimmee, FL 34747

Move-in ready • Low hoa fees • Roof replaced

Property at 1115 Park Ridge Cir, Kissimmee, FL 34746, 3 beds, 2.5 baths

$245,000

3 beds2.5 baths1,291 sq ft

1115 Park Ridge Cir, Kissimmee, FL 34746

Property at 2569 Folio Way, Kissimmee, FL 34741, 3 beds, 2.5 baths

$365,000

3 beds2.5 baths1,690 sq ft

2569 Folio Way, Kissimmee, FL 34741

Property at 173 Lavenna Ave, Saint Cloud, FL 34771, 4 beds, 2 baths

$439,000

4 beds2 baths2,020 sq ft

173 Lavenna Ave, Saint Cloud, FL 34771

Property at 7564 Marker Ave, Kissimmee, FL 34747, 5 beds, 5.5 baths

$695,000

5 beds5.5 baths3,328 sq ft

7564 Marker Ave, Kissimmee, FL 34747

Property at 2904 Grafton Dr, Kissimmee, FL 34741, 3 beds, 2.5 baths

$310,000

3 beds2.5 baths2,013 sq ft

2904 Grafton Dr, Kissimmee, FL 34741

Property at 1592 Moon Valley Dr, Davenport, FL 33896, 4 beds, 3 baths

$365,000

4 beds3 baths1,902 sq ft

1592 Moon Valley Dr, Davenport, FL 33896

Property at 2691 Andros Ln, Kissimmee, FL 34747, 3 beds, 2.5 baths

$265,000

3 beds2.5 baths1,595 sq ft

2691 Andros Ln, Kissimmee, FL 34747

Property at 1549 Fairview Cir, Reunion, FL 34747, 4 beds, 2.5 baths

$484,900

4 beds2.5 baths2,296 sq ft

1549 Fairview Cir, Reunion, FL 34747

Property at 7917 NW Spectrum Dr, Reunion, FL 34747, 3 beds, 2.5 baths

$339,900

3 beds2.5 baths1,704 sq ft

7917 NW Spectrum Dr, Reunion, FL 34747

Property at 3100 Parkway Blvd #726, Kissimmee, FL 34747, 1 bed, 1 bath

$120,000

1 bed1 bath524 sq ft

3100 Parkway Blvd #726, Kissimmee, FL 34747

Property at 2824 Noble Crow Dr, Kissimmee, FL 34744, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths2,676 sq ft

2824 Noble Crow Dr, Kissimmee, FL 34744

Property at 246 Zircon Rd, Kissimmee, FL 34758, 6 beds, 5 baths

$470,000

6 beds5 baths3,003 sq ft

246 Zircon Rd, Kissimmee, FL 34758

(888) 883-8509

Property at 8051 White Crane Ct, Kissimmee, FL 34747, 4 beds, 2.5 baths

$555,000

4 beds2.5 baths2,021 sq ft

8051 White Crane Ct, Kissimmee, FL 34747

Property at 634 Grape Ave, Saint Cloud, FL 34769, 3 beds, 2 baths

$565,000

3 beds2 baths1,753 sq ft

634 Grape Ave, Saint Cloud, FL 34769

Property at 4811 Pliny Ct, Kissimmee, FL 34746, 3 beds, 2 baths

$356,000

3 beds2 baths1,570 sq ft

4811 Pliny Ct, Kissimmee, FL 34746

Property at 3141 Sun Lake Ct Unit A, Kissimmee, FL 34747, 3 beds, 2 baths

$247,500

3 beds2 baths1,484 sq ft

3141 Sun Lake Ct Unit A, Kissimmee, FL 34747

Property at 3941 Southern Vista Loop, Saint Cloud, FL 34772, 5 beds, 3 baths

$500,000

5 beds3 baths2,791 sq ft

3941 Southern Vista Loop, Saint Cloud, FL 34772

Property at 2794 Holiday Woods Dr, Kissimmee, FL 34744, 4 beds, 3 baths

$2,250,000

4 beds3 baths2,970 sq ft

2794 Holiday Woods Dr, Kissimmee, FL 34744

Property at 3036 Parkway Blvd #205, Kissimmee, FL 34747, 2 beds, 2 baths

$210,000

2 beds2 baths937 sq ft

3036 Parkway Blvd #205, Kissimmee, FL 34747

Property at 7846 Palmilla Ct, Reunion, FL 34747, 8 beds, 9 baths

$2,099,000

8 beds9 baths5,945 sq ft

7846 Palmilla Ct, Reunion, FL 34747

Property at 200 Pendant Ct, Kissimmee, FL 34747, 6 beds, 6.5 baths

$619,000

6 beds6.5 baths3,317 sq ft

200 Pendant Ct, Kissimmee, FL 34747

Property at 2516 Datura Loop, Saint Cloud, FL 34772, 2 beds, 2 baths

$275,000

2 beds2 baths1,346 sq ft

2516 Datura Loop, Saint Cloud, FL 34772

Property at 2431 Grasmere View Pkwy N, Kissimmee, FL 34746, 2 beds, 2.5 baths

$247,900

2 beds2.5 baths1,820 sq ft

2431 Grasmere View Pkwy N, Kissimmee, FL 34746

Property at 6035 Blue View Way, Saint Cloud, FL 34771, 5 beds, 4 baths

$650,000

5 beds4 baths3,329 sq ft

6035 Blue View Way, Saint Cloud, FL 34771

Property at 7505 Mourning Dove Cir #303, Reunion, FL 34747, 3 beds, 2 baths

$299,000

3 beds2 baths1,354 sq ft

7505 Mourning Dove Cir #303, Reunion, FL 34747

Property at 7740 Sandy Ridge Dr #228, Reunion, FL 34747, 5 beds, 4.5 baths

$390,000

5 beds4.5 baths2,703 sq ft

7740 Sandy Ridge Dr #228, Reunion, FL 34747

Property at 5367 W Irlo Bronson Memorial Hwy Unit 2-214, Kissimmee, FL 34746, 1 bed, 1 bath

$57,000

1 bed1 bath198 sq ft

5367 W Irlo Bronson Memorial Hwy Unit 2-214, Kissimmee, FL 34746

Property at 865 Desert Mountain Ct, Reunion, FL 34747, 6 beds, 5.5 baths

$1,499,000

6 beds5.5 baths4,643 sq ft

865 Desert Mountain Ct, Reunion, FL 34747

Property at 2080 Heritage Key Blvd, Kissimmee, FL 34744, 3 beds, 2.5 baths

$275,000

3 beds2.5 baths1,512 sq ft

2080 Heritage Key Blvd, Kissimmee, FL 34744

Property at 6699 Alder Rd, Harmony, FL 34773, 4 beds, 3 baths

$420,000

4 beds3 baths2,361 sq ft

6699 Alder Rd, Harmony, FL 34773

Property at 4793 Kings Castle Cir, Kissimmee, FL 34746, 6 beds, 6 baths

$819,000

6 beds6 baths3,291 sq ft

4793 Kings Castle Cir, Kissimmee, FL 34746

Property at 1416 6th St, Saint Cloud, FL 34769, 2 beds, 1 bath

$269,500

2 beds1 bath808 sq ft

1416 6th St, Saint Cloud, FL 34769

Property at 4997 Town Ter S, Kissimmee, FL 34758, 3 beds, 3 baths

$239,900

3 beds3 baths1,504 sq ft

4997 Town Ter S, Kissimmee, FL 34758

Property at 5338 Spoonflower Ct, Saint Cloud, FL 34771, 3 beds, 2 baths

$357,900

3 beds2 baths1,515 sq ft

5338 Spoonflower Ct, Saint Cloud, FL 34771

Property at 865 Seagrove Trl, Saint Cloud, FL 34771, 5 beds, 3 baths

$486,990

5 beds3 baths2,490 sq ft

865 Seagrove Trl, Saint Cloud, FL 34771

Property at 1799 Ranger Highlands Rd, Kindred, FL 34744, 4 beds, 3.5 baths

$549,900

4 beds3.5 baths2,851 sq ft

1799 Ranger Highlands Rd, Kindred, FL 34744

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Based on information submitted to the MLS GRID as of Fri Sep 25 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 3533 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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