Homes with Pools for Sale in Osceola County, FL

3,535 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Preservation area view and Phase 1 location set the tone for this well-positioned 3-bedroom, 2.5-bath two-story townhome in Emerald Island Resort. This property offers close proximity to the clubhouse and main resort amenities while also backing directly to a conservation area, providing peaceful natural views and added privacy. The first floor features an open-concept layout with a spacious living room, dining area, and kitchen, along with a half bath and separate laundry room. Upstairs, all three bedrooms and two full bathrooms are located together, including the primary suite with its own private balcony overlooking the surroundings. Situated within the gated and 24-hour guard-gated Emer

$265,000

3 beds2.5 baths1,291 sq ft

2743 Sun Key Pl, Kissimmee, FL 34747

Gated community • Private balcony • $672 HOA

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Turn-Key Pool Townhome in Guard-Gated Paradise Palms Resort! Discover the ultimate combination of vacation luxury and premium investment potential in this beautifully maintained, fully furnished 4-bedroom, 3-bathroom townhome. Boasting a highly desirable, serene waterfront lot, this property is fully zoned for short-term vacation rentals and comes 100% turn-key and ready to generate income or welcome you home from day one! Interior & Multi-Generational Layout: First-Floor Flexibility: The main level features a bright, open-concept living and dining area seamlessly connected to a modern kitchen with granite countertops and stainless steel appliances. A convenient downstairs bedroom and

$319,999

4 beds3 baths1,902 sq ft

8847 Candy Palm Rd, Kissimmee, FL 34747

Arcade game room • Resort amenities • Guard-gated access

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to 7721 Fairfax Dr, Kissimmee, a stunning fully furnished 8-bedroom, 6.5-bath luxury home located in the gated Encore Resort at Reunion, just minutes from Disney and Orlando’s top attractions. Designed for both relaxation and entertainment, this turnkey residence features an open floor plan with a gourmet kitchen, spacious living areas, a themed game and movie room, and beautifully decorated bedrooms throughout. Step outside to enjoy your private heated pool and spa, extended lanai, and a custom-built outdoor mini golf putting area, perfect for family fun and guest entertainment. As part of Encore Resort, owners and guests enjoy access to world-class amenities including a wate

$959,000

8 beds6.5 baths3,612 sq ft

7721 Fairfax Dr, Kissimmee, FL 34747

Private heated pool • Gated encore resort • Water park

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to 2260 Rapollo Drive, a beautifully upgraded Mattamy Homes residence located in the highly sought-after gated community of Tapestry in Kissimmee. Situated on a premium corner lot, this stunning two-story home offers the perfect combination of modern design, comfort, privacy, and convenience. Built in 2019 and meticulously maintained, the property showcases over 2,100 square feet of thoughtfully designed living space featuring 4 spacious bedrooms, 2.5 bathrooms, a flex room, an attached 2-car garage, and exceptional indoor-outdoor living areas. From the moment you arrive, the enhanced curb appeal stands out with its upgraded paver driveway, professional landscaping, perimeter pavers

$513,990

4 beds2.5 baths2,138 sq ft

2260 Rapollo Dr, Kissimmee, FL 34741

Gated community • Premium corner lot • Gourmet kitchen

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to this stunning, move-in-ready home located in the highly desirable North Pointe community of Kissimmee. This residence offers an exceptional balance of comfort, quality upgrades, and resort-style outdoor living. Step inside to discover tile flooring throughout the entire home, creating a seamless, low-maintenance living space. Beautiful plantation shutters add timeless charm and refined character in every room. The home also includes a RainSoft salt-water purification system, providing clean, soft water throughout. The kitchen comes fully equipped with all major appliances, including washer, dryer, refrigerator, stove, microwave, and dishwasher — making this home truly move-

$524,000

3 beds2 baths1,941 sq ft

4461 Indigo Sky Ln, Kissimmee, FL 34744

Plantation shutters • Tile flooring • Roof replaced

Property at 2784 Almaton Loop #301, Kissimmee, FL 34747, 3 beds, 2 baths

$304,000

3 beds2 baths1,246 sq ft

2784 Almaton Loop #301, Kissimmee, FL 34747

Property at 2743 River Creek Ln, Saint Cloud, FL 34771, 3 beds, 2.5 baths

$648,500

3 beds2.5 baths2,321 sq ft

2743 River Creek Ln, Saint Cloud, FL 34771

Property at 2427 Zaballina Pl, Davenport, FL 33897, 4 beds, 3 baths

$529,000

4 beds3 baths2,272 sq ft

2427 Zaballina Pl, Davenport, FL 33897

Property at 340 Chiquita Ct, Kissimmee, FL 34758, 3 beds, 2 baths

$265,000

3 beds2 baths1,053 sq ft

340 Chiquita Ct, Kissimmee, FL 34758

Property at 1241 Challenge Dr, Davenport, FL 33896, 7 beds, 5 baths

$639,000

7 beds5 baths4,019 sq ft

1241 Challenge Dr, Davenport, FL 33896

Property at 2810 Swoop Cir, Kissimmee, FL 34741, 4 beds, 3 baths

$710,000

4 beds3 baths3,410 sq ft

2810 Swoop Cir, Kissimmee, FL 34741

Property at 1113 Park Ridge Cir, Kissimmee, FL 34746, 3 beds, 2.5 baths

$249,900

3 beds2.5 baths1,277 sq ft

1113 Park Ridge Cir, Kissimmee, FL 34746

Property at 4609 Formby Ct, Kissimmee, FL 34746, 4 beds, 3 baths

$470,000

4 beds3 baths1,844 sq ft

4609 Formby Ct, Kissimmee, FL 34746

Property at 2705 Impala Ln, Kissimmee, FL 34746, 3 beds, 2.5 baths

$330,000

3 beds2.5 baths1,435 sq ft

2705 Impala Ln, Kissimmee, FL 34746

Property at 7962 Rumney Ln, Reunion, FL 34747, 3 beds, 2 baths

$400,000

3 beds2 baths1,553 sq ft

7962 Rumney Ln, Reunion, FL 34747

Property at Undisclosed address, Kissimmee, FL 34747, 5 beds, 5 baths

$609,000

5 beds5 baths2,297 sq ft

Undisclosed address, Kissimmee, FL 34747

Property at 3121 Paradox Cir #301, Kissimmee, FL 34746, 3 beds, 2 baths

$375,000

3 beds2 baths1,329 sq ft

3121 Paradox Cir #301, Kissimmee, FL 34746

Property at 2253 Celebration Blvd, Celebration, FL 34747, 3 beds, 2.5 baths

$549,000

3 beds2.5 baths1,638 sq ft

2253 Celebration Blvd, Celebration, FL 34747

Property at 202 Woodson Ct, Kissimmee, FL 34744, 5 beds, 3.5 baths

$595,000

5 beds3.5 baths3,744 sq ft

202 Woodson Ct, Kissimmee, FL 34744

Property at 1301 Seven Eagles Ct #1301, Reunion, FL 34747, 3 beds, 3 baths

$390,000

3 beds3 baths2,124 sq ft

1301 Seven Eagles Ct #1301, Reunion, FL 34747

Property at 2701 Timbergrove St, Saint Cloud, FL 34771, 3 beds, 3 baths

$715,000

3 beds3 baths2,500 sq ft

2701 Timbergrove St, Saint Cloud, FL 34771

Property at 3491 Allegra Cir, St Cloud, FL 34772, 3 beds, 2.5 baths

$263,000

3 beds2.5 baths1,596 sq ft

3491 Allegra Cir, St Cloud, FL 34772

Property at 3180 Canter Ln, Kissimmee, FL 34746, 3 beds, 2 baths

$833,000

3 beds2 baths2,360 sq ft

3180 Canter Ln, Kissimmee, FL 34746

Property at 8816 Dunes Ct #302, Kissimmee, FL 34747, 2 beds, 2 baths

$215,000

2 beds2 baths1,110 sq ft

8816 Dunes Ct #302, Kissimmee, FL 34747

Property at 2314 Nuthatch St, Saint Cloud, FL 34771, 6 beds, 3.5 baths

$620,000

6 beds3.5 baths4,201 sq ft

2314 Nuthatch St, Saint Cloud, FL 34771

Property at 1796 Tohoqua Blvd, Kissimmee, FL 34744, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths1,755 sq ft

1796 Tohoqua Blvd, Kissimmee, FL 34744

Property at 2202 Key West Ct #626, Kissimmee, FL 34741, 2 beds, 2 baths

$169,997

2 beds2 baths1,026 sq ft

2202 Key West Ct #626, Kissimmee, FL 34741

Property at 2863 Boating Blvd, Kissimmee, FL 34746, 4 beds, 2.5 baths

$418,999

4 beds2.5 baths— sq ft

2863 Boating Blvd, Kissimmee, FL 34746

(305) 809-8085

Property at 3150 Wet N Wild Ct, Kissimmee, FL 34746, 2 beds, 2 baths

$250,000

2 beds2 baths1,052 sq ft

3150 Wet N Wild Ct, Kissimmee, FL 34746

Property at 2015 Majorca Dr, Kissimmee, FL 34747, 5 beds, 4.5 baths

$412,900

5 beds4.5 baths2,263 sq ft

2015 Majorca Dr, Kissimmee, FL 34747

Property at 5311 Amersham Ln, Saint Cloud, FL 34771, 5 beds, 3 baths

$445,000

5 beds3 baths2,566 sq ft

5311 Amersham Ln, Saint Cloud, FL 34771

Property at 253 Southfield St, Kissimmee, FL 34747, 5 beds, 5.5 baths

$709,900

5 beds5.5 baths2,945 sq ft

253 Southfield St, Kissimmee, FL 34747

Property at 4836 Tribute Trl, Kissimmee, FL 34746, 3 beds, 2.5 baths

$345,000

3 beds2.5 baths1,797 sq ft

4836 Tribute Trl, Kissimmee, FL 34746

Property at 2900 Edenshire Way #107, Kissimmee, FL 34746, 3 beds, 2 baths

$280,000

3 beds2 baths1,300 sq ft

2900 Edenshire Way #107, Kissimmee, FL 34746

Property at 7667 Otterspool St, Kissimmee, FL 34747, 3 beds, 3 baths

$449,000

3 beds3 baths1,440 sq ft

7667 Otterspool St, Kissimmee, FL 34747

Property at 2473 Independence Ln, Saint Cloud, FL 34772, 2 beds, 2 baths

$235,000

2 beds2 baths1,556 sq ft

2473 Independence Ln, Saint Cloud, FL 34772

Property at 7833 Marlow Pl, Kissimmee, FL 34747, 6 beds, 4.5 baths

$570,900

6 beds4.5 baths2,714 sq ft

7833 Marlow Pl, Kissimmee, FL 34747

Property at 4006 Venetian Bay Dr #108, Kissimmee, FL 34741, 4 beds, 3 baths

$257,000

4 beds3 baths1,470 sq ft

4006 Venetian Bay Dr #108, Kissimmee, FL 34741

Property at 3176 Feltrim Pl #302, Kissimmee, FL 34747, 2 beds, 2 baths

$249,900

2 beds2 baths1,062 sq ft

3176 Feltrim Pl #302, Kissimmee, FL 34747

Property at 2135 Water Mania Ct, Kissimmee, FL 34746, 2 beds, 2 baths

$250,000

2 beds2 baths1,052 sq ft

2135 Water Mania Ct, Kissimmee, FL 34746

Property at 1829 Gobi Dr, Kissimmee, FL 34747, 8 beds, 6 baths

$629,000

8 beds6 baths4,041 sq ft

1829 Gobi Dr, Kissimmee, FL 34747

Viewing page 49 of 87

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 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.

More real estate resources for Osceola County, FL

Cities

Nearby Counties

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Osceola County, FL

How to buy a house in Osceola County, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

8 Redfin agents serving Osceola County

169

Deals*

4.9

Satisfaction

1102

Homes closed*

* Data from the last year

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.