Homes with Pools for Sale in Osceola County, FL

3,531 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Near Disney and Margaritaville, this well-appointed 3-bedroom, 2-bath condo offers an exceptional opportunity for a vacation home, primary residence, or short-term rental investment. Featuring a larger floor plan than many units within the community, the spacious layout includes an oversized living area, generously sized bedrooms, and a private balcony perfect for relaxing or entertaining guests while enjoying the Florida breeze. Ideally positioned just steps from the Wyndham Palms Resort clubhouse, residents and guests enjoy access to an impressive range of resort-style amenities, including a community pool, restaurant, café, mini-market, movie theater, fitness center, video arcade,

$205,000

3 beds2 baths1,402 sq ft

8103 Coconut Palm Way #205, Kissimmee, FL 34747

Fitness center • Community pool • Private balcony

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to this beautifully maintained 5-bedroom, 5-bath pool home located just 5 miles from Walt Disney World® in the highly desirable Windsor Hills Resort. Situated on a premium corner lot with a west-facing front and unobstructed conservation views, this property offers privacy, strong rental appeal, and an ideal layout for both personal use and short-term rental investment. The open floor plan features a spacious central living area with multiple dining options including a formal 8-seat dining table, breakfast nook, and kitchen bar seating. The fully equipped kitchen overlooks the main living space, creating an ideal setup for entertaining. The converted garage has been transformed

$639,000

5 beds5 baths2,297 sq ft

2621 Archfeld Blvd, Kissimmee, FL 34747

Premium corner lot • Screened-in lanai • Converted garage

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Luxury 10-Bedroom Golf Front Estate in Reunion Resort. This property comes with the Gold Membership and access to Golf, Water Parks and the Tennis Facilities. – Fully Turnkey Investment Opportunity Welcome to an exceptional 10-bedroom, 9.5-bath luxury estate perfectly positioned on a premium oversized lot backing directly onto the golf course—offering rare privacy and stunning views just off the tee box in Reunion Resort. This fully furnished, turnkey vacation home is designed to impress, combining high-end living with unbeatable income potential. Property Highlights 10 Bedrooms | 9.5 Bathrooms 3 Bedrooms on the ground floor, ideal for multi-generational living 7 Bedr

$1,999,999

10 beds9.5 baths5,563 sq ft

7442 Gathering Ct, Kissimmee, FL 34747

Custom karaoke stage • Private theater room • Themed bedrooms

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Experience luxury living in this stunning Toll Brothers Bunnell Farmhouse Transitional home, featuring 5 bedrooms and 4.1 bathrooms in the highly sought-after Weslyn Park at Sunbridge community. Backing to a beautiful conservation area, this exceptional property offers privacy and peaceful views to enjoy from your own private pool. From the moment you step into the grand foyer, you are welcomed by an abundance of natural light and an elegant, open-concept design. The gourmet kitchen is truly the heart of the home, overlooking the spacious great room and casual dining area, making it perfect for entertaining. Featuring extensive counter space, premium finishes, and a large center island, thi

$899,000

5 beds4.5 baths3,232 sq ft

6422 Trailblaze Bnd, Saint Cloud, FL 34771

Private pool • Gourmet kitchen • Expansive loft

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
GORGEOUS 2-Story Cottage in Margaritaville Resort Orlando! FULLY FURNISHED with MRO Approved City Furniture "CARIBBEAN OASIS". This BEAUTIFUL 1539-C Model Features 3 Bedrooms and 3 Bathrooms and the 'SON OF A SAILOR' INTERIOR UPGRADES. Home Features Primary En Suite Bedroom Located on First Floor, QUARTZ Countertops, Ceiling Fans, Upgraded Appliances, High Ceilings, 'WOOD' Tile Flooring Throughout. Upstairs You Will Find Two More Bedrooms (One En Suite), a BONUS Room With Twin Bed and High Capacity Washer and Dryer. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES ALL Furniture and Housewares, Also I

$472,000

4 beds3 baths1,564 sq ft

8067 Knee Deep Rd, Kissimmee, FL 34747

Quartz countertops • Ceiling fans • Bonus room

Property at 8045 Lost Shaker Ln, Kissimmee, FL 34747, 4 beds, 4.5 baths

$575,000

4 beds4.5 baths1,948 sq ft

8045 Lost Shaker Ln, Kissimmee, FL 34747

Property at 1008 Coyote Creek Way, Reunion, FL 34747, 8 beds, 9.5 baths

$2,195,900

8 beds9.5 baths5,963 sq ft

1008 Coyote Creek Way, Reunion, FL 34747

Property at 5533 Vigo Loop, Saint Cloud, FL 34771, 4 beds, 3.5 baths

$385,000

4 beds3.5 baths2,222 sq ft

5533 Vigo Loop, Saint Cloud, FL 34771

Property at 2916 ON The Rocks Pt, Kissimmee, FL 34747, 3 beds, 3 baths

$359,999

3 beds3 baths1,545 sq ft

2916 ON The Rocks Pt, Kissimmee, FL 34747

Property at 1200 Grand Traverse Pkwy, Reunion, FL 34747, 10 beds, 10.5 baths

$3,250,000

10 beds10.5 baths8,020 sq ft

1200 Grand Traverse Pkwy, Reunion, FL 34747

Property at 3231 Agostino Ter, Kissimmee, FL 34746, 4 beds, 3 baths

$550,000

4 beds3 baths2,840 sq ft

3231 Agostino Ter, Kissimmee, FL 34746

Property at 5105 Star Line Dr, Saint Cloud, FL 34771, 3 beds, 2 baths

$664,900

3 beds2 baths2,261 sq ft

5105 Star Line Dr, Saint Cloud, FL 34771

Property at 615 Mckinley Ct, Kissimmee, FL 34758, 3 beds, 2 baths

$285,000

3 beds2 baths1,449 sq ft

615 Mckinley Ct, Kissimmee, FL 34758

Property at 1020 Siena Park Blvd W #103, Celebration, FL 34747, 1 bed, 1 bath

$220,000

1 bed1 bath792 sq ft

1020 Siena Park Blvd W #103, Celebration, FL 34747

Property at 1001 Park Ridge Cir, Kissimmee, FL 34746, 4 beds, 3.5 baths

$255,000

4 beds3.5 baths1,645 sq ft

1001 Park Ridge Cir, Kissimmee, FL 34746

Property at 1341 Shinnecock Hills Dr, Davenport, FL 33896, 4 beds, 4 baths

$309,990

4 beds4 baths2,596 sq ft

1341 Shinnecock Hills Dr, Davenport, FL 33896

Property at 437 Hunter Cir, Kissimmee, FL 34758, 2 beds, 2 baths

$150,000

2 beds2 baths1,038 sq ft

437 Hunter Cir, Kissimmee, FL 34758

Property at 2234 W Maple Ter, Saint Cloud, FL 34771, 3 beds, 2 baths

$429,900

3 beds2 baths1,504 sq ft

2234 W Maple Ter, Saint Cloud, FL 34771

Property at 4460 Nirvana Pkwy, Kissimmee, FL 34746, 5 beds, 4.5 baths

$489,000

5 beds4.5 baths2,509 sq ft

4460 Nirvana Pkwy, Kissimmee, FL 34746

Property at 1947 Bentley Blvd, Kissimmee, FL 34741, 3 beds, 2 baths

$224,901

3 beds2 baths1,056 sq ft

1947 Bentley Blvd, Kissimmee, FL 34741

Property at 513 Berry James Ct, Kissimmee, FL 34744, 4 beds, 2.5 baths

$377,500

4 beds2.5 baths2,191 sq ft

513 Berry James Ct, Kissimmee, FL 34744

Property at 9254 Sommerset Hills Dr, Davenport, FL 33896, 9 beds, 5 baths

$695,000

9 beds5 baths4,356 sq ft

9254 Sommerset Hills Dr, Davenport, FL 33896

Property at 4619 Cabalerro Trl, Kissimmee, FL 34758, 3 beds, 2 baths

$344,990

3 beds2 baths1,770 sq ft

4619 Cabalerro Trl, Kissimmee, FL 34758

Property at 569 Hunter Cir, Kissimmee, FL 34758, 2 beds, 2 baths

$168,999

2 beds2 baths1,038 sq ft

569 Hunter Cir, Kissimmee, FL 34758

Property at 7602 Sandy Ridge Dr #103, Reunion, FL 34747, 3 beds, 3 baths

$320,000

3 beds3 baths1,630 sq ft

7602 Sandy Ridge Dr #103, Reunion, FL 34747

Property at 5248 Landmark Dr, Saint Cloud, FL 34771, 5 beds, 3.5 baths

$615,000

5 beds3.5 baths3,300 sq ft

5248 Landmark Dr, Saint Cloud, FL 34771

Property at 7407 Oconee St, Reunion, FL 34747, 4 beds, 4 baths

$629,000

4 beds4 baths1,906 sq ft

7407 Oconee St, Reunion, FL 34747

Property at 2731 N Poinciana Blvd #107, Kissimmee, FL 34746, 3 beds, 2 baths

$195,000

3 beds2 baths1,287 sq ft

2731 N Poinciana Blvd #107, Kissimmee, FL 34746

Property at 8019 Knee Deep Rd, Kissimmee, FL 34747, 5 beds, 5.5 baths

$724,500

5 beds5.5 baths1,908 sq ft

8019 Knee Deep Rd, Kissimmee, FL 34747

Property at 4940 Blanche Ct, Saint Cloud, FL 34772, 3 beds, 2 baths

$560,000

3 beds2 baths2,130 sq ft

4940 Blanche Ct, Saint Cloud, FL 34772

Property at 4017 Venetian Bay Dr #103, Kissimmee, FL 34741, 3 beds, 2 baths

$199,000

3 beds2 baths1,296 sq ft

4017 Venetian Bay Dr #103, Kissimmee, FL 34741

Property at 7770 Sandy Ridge Dr Unit 218 BLDG 28 - Elevator, Reunion, FL 34747, 5 beds, 4.5 baths

$393,000

5 beds4.5 baths2,630 sq ft

7770 Sandy Ridge Dr Unit 218 BLDG 28 - Elevator, Reunion, FL 34747

Property at 8363 Bella Tierra Ct, Davenport, FL 33896, 2 beds, 2 baths

$239,999

2 beds2 baths1,504 sq ft

8363 Bella Tierra Ct, Davenport, FL 33896

Property at 1709 Michigan Ave Unit C, Kissimmee, FL 34744, 2 beds, 2 baths

$119,900

2 beds2 baths1,118 sq ft

1709 Michigan Ave Unit C, Kissimmee, FL 34744

Property at 3000 Ella Way, Saint Cloud, FL 34771, 4 beds, 3 baths

$640,000

4 beds3 baths2,644 sq ft

3000 Ella Way, Saint Cloud, FL 34771

Property at 6098 Windy Leaf Aly, Saint Cloud, FL 34771, 4 beds, 3 baths

$399,000

4 beds3 baths2,490 sq ft

6098 Windy Leaf Aly, Saint Cloud, FL 34771

Property at 3759 Eagle Isle Cir, Kissimmee, FL 34746, 6 beds, 5 baths

$550,000

6 beds5 baths3,651 sq ft

3759 Eagle Isle Cir, Kissimmee, FL 34746

Property at 4731 Clock Tower Dr #206, Kissimmee, FL 34746, 2 beds, 2 baths

$279,800

2 beds2 baths1,196 sq ft

4731 Clock Tower Dr #206, Kissimmee, FL 34746

Property at 2537 Longpine Ln, Saint Cloud, FL 34772, 2 beds, 2 baths

$164,900

2 beds2 baths1,558 sq ft

2537 Longpine Ln, Saint Cloud, FL 34772

Property at 7755 Grassendale St, Kissimmee, FL 34747, 4 beds, 4 baths

$585,000

4 beds4 baths1,824 sq ft

7755 Grassendale St, Kissimmee, FL 34747

Property at 1851 Coastal Ct, Celebration, FL 34747, 3 beds, 2.5 baths

$670,000

3 beds2.5 baths1,845 sq ft

1851 Coastal Ct, Celebration, FL 34747

Viewing page 56 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 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.

More real estate resources for Osceola County, FL

Nearby Counties

Cities

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.