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:
Beautiful end-unit Townhome located in a gated Community just 2.5 miles from Walt Disney World, and minutes from major highways I4 and Hwy 192 offering easy access to shopping, dining, attractions, resorts, and Walmart. This is the largest 3 bedroom 2 bath townhome in Crestwynd Bay that was offered by KB Homes. Perfect for both primary homeowners or investors. This unit is zoned for A rated Celebration School and can be used for primary, long term, or short term rental, which makes this the ideal place to call home or your home away from home. The flooring consists of tile in the wet areas and laminate first floor while the second floor carpet throughout. The kitchen offers 42 inch cabinet

$290,000

3 beds2.5 baths1,595 sq ft

2682 Mayaguana St, Kissimmee, FL 34747

Gated community • End unit • Largest townhome

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
$75,000 IN FUTURE BOOKINGS!! Welcome to 1430 Moon Valley Drive, a stunning 8-bedroom, 5-bathroom luxury retreat located on a premium corner lot within the highly sought-after, guard-gated community of Champions Gate. Whether you’re searching for a high-performing short-term rental investment or a spacious vacation getaway, this fully furnished home delivers both style and opportunity. Thoughtfully updated, the property features brand-new flooring, fresh interior paint, new appliances, a 2025 HVAC system, 2025 pool heater, and a 2025 water heater. The garage offers flexible space ideal for a game room, entertainment area, or potential 9th bedroom, while the dedicated theater room provi

$664,900

8 beds5 baths3,909 sq ft

1430 Moon Valley Dr, Davenport, FL 33896

Premium corner lot • Brand new flooring • New appliances

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Step into a fully immersive, superhero-themed vacation home—complete with bookings already secured through 2027. This fully turnkey, income-producing property offers a rare opportunity for immediate cash flow with zero renovation or update needs, whether you’re expanding your portfolio or securing the ultimate family vacation retreat. Thoughtfully designed with exceptional attention to detail, the custom-themed décor and high-quality furnishings create an unforgettable guest experience that drives strong reviews and repeat bookings. Featuring six spacious bedrooms and six bathrooms, this home comfortably accommodates large groups. Durable laminate flooring flows throughou

$625,000

6 beds6 baths3,465 sq ft

9027 Shadow Mountain St, Davenport, FL 33896

Upstairs loft • Oversized pool • Custom themed decor

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
The Winona is an exceptional two-story home designed for family living with a large, open family room that seamlessly connects to the adjoining kitchen and dining room, creating the perfect space for entertaining. The chef-ready kitchen is equipped with top-of-the-line stainless steel Whirlpool® appliances, gorgeous quartz countertops, and beautiful white cabinets, making it the perfect place to cook and gather. The master retreat, located on the first floor, offers a spacious peaceful escape with and an en-suite bathroom for ultimate relaxation. Upstairs, you'll find three spacious bedrooms, making this home a perfect fit for a growing family. Modern conveniences like a Wi-Fi-enabled g

$484,900

4 beds3.5 baths2,158 sq ft

7665 Somersworth Dr, Kissimmee, FL 34747

Master retreat • Quartz countertops • Chef-ready kitchen

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to Storey Lake Resort! This beautifully 2-bedroom, 2-bathroom condo is ideally located just minutes from Disney and major highways—perfect as a primary residence, vacation home, or income-producing investment. Situated on the 3rd floor with convenient elevator access, the unit features an open-concept layout with tile flooring throughout the entire unit, and comfortable carpet in the bedrooms. The modern kitchen is equipped with granite countertops, offering both style and functionality. Enjoy a private balcony with lovely views, plus the convenience of a washer and dryer in-unit. Short-term rentals are allowed, giving you the flexibility to live in the property, use it as a v

$295,000

2 beds2 baths1,126 sq ft

3150 Paradox Cir #305, Kissimmee, FL 34746

Clubhouse • Private balcony • Washer and dryer

Property at 4507 Monado Dr, Kissimmee, FL 34746, 6 beds, 6 baths

$595,000

6 beds6 baths3,042 sq ft

4507 Monado Dr, Kissimmee, FL 34746

Property at 7593 Gathering Dr #608, Reunion, FL 34747, 1 bed, 1 bath

$329,900

1 bed1 bath1,128 sq ft

7593 Gathering Dr #608, Reunion, FL 34747

Property at 2639 Buena View Rd, Kissimmee, FL 34746, 3 beds, 2.5 baths

$344,000

3 beds2.5 baths1,699 sq ft

2639 Buena View Rd, Kissimmee, FL 34746

Property at 5052 Center Ct, Saint Cloud, FL 34772, 5 beds, 3 baths

$562,000

5 beds3 baths3,166 sq ft

5052 Center Ct, Saint Cloud, FL 34772

Property at 8550 Crystal Cove Loop, Kissimmee, FL 34747, 3 beds, 2.5 baths

$289,900

3 beds2.5 baths1,277 sq ft

8550 Crystal Cove Loop, Kissimmee, FL 34747

Property at 4511 Monado Dr, Kissimmee, FL 34746, 5 beds, 5 baths

$549,995

5 beds5 baths3,042 sq ft

4511 Monado Dr, Kissimmee, FL 34746

Property at 7568 Sunflower Cir, Kissimmee, FL 34747, 3 beds, 3 baths

$419,000

3 beds3 baths1,530 sq ft

7568 Sunflower Cir, Kissimmee, FL 34747

Property at 3006 Bonfire Beach Dr #204, Kissimmee, FL 34746, 2 beds, 2 baths

$249,000

2 beds2 baths1,192 sq ft

3006 Bonfire Beach Dr #204, Kissimmee, FL 34746

Property at 2139 Balboa Way, Kissimmee, FL 34741, 2 beds, 2.5 baths

$258,900

2 beds2.5 baths1,418 sq ft

2139 Balboa Way, Kissimmee, FL 34741

Property at 3000 Maingate Ln #319, Kissimmee, FL 34747, 1 bath

$48,500

Studio1 bath304 sq ft

3000 Maingate Ln #319, Kissimmee, FL 34747

Property at 2685 Great Heron Ave, Harmony, FL 34773, 5 beds, 3.5 baths

$622,310

5 beds3.5 baths3,120 sq ft

2685 Great Heron Ave, Harmony, FL 34773

Property at 3151 Sunset Walk Dr #402, Kissimmee, FL 34747, 1 bed, 1 bath

$329,900

1 bed1 bath745 sq ft

3151 Sunset Walk Dr #402, Kissimmee, FL 34747

Property at 1069 Leader St, Davenport, FL 33896, 6 beds, 5 baths

$590,000

6 beds5 baths3,291 sq ft

1069 Leader St, Davenport, FL 33896

Property at 9179 Breeze Mist Ter, Davenport, FL 33897, 9 beds, 6.5 baths

$1,450,000

9 beds6.5 baths4,363 sq ft

9179 Breeze Mist Ter, Davenport, FL 33897

Property at 2717 N Poinciana Blvd #176, Kissimmee, FL 34746, 2 beds, 2 baths

$230,000

2 beds2 baths1,087 sq ft

2717 N Poinciana Blvd #176, Kissimmee, FL 34746

Property at 522-524 Imperial Pl, Kissimmee, FL 34758, 6 beds, 4 baths

$455,000

6 beds4 baths2,310 sq ft

522-524 Imperial Pl, Kissimmee, FL 34758

Property at 9023 Shadow Mountain St, Davenport, FL 33896, 5 beds, 4.5 baths

$535,000

5 beds4.5 baths2,842 sq ft

9023 Shadow Mountain St, Davenport, FL 33896

Property at 9144 Driftwood Path, Kissimmee, FL 34747, 7 beds, 6.5 baths

$1,060,000

7 beds6.5 baths3,533 sq ft

9144 Driftwood Path, Kissimmee, FL 34747

Property at 1424 Clubman Dr, Davenport, FL 33896, 4 beds, 2 baths

$479,000

4 beds2 baths2,269 sq ft

1424 Clubman Dr, Davenport, FL 33896

Property at 2787 Punctuation Pl, Kissimmee, FL 34746, 5 beds, 5 baths

$750,000

5 beds5 baths2,996 sq ft

2787 Punctuation Pl, Kissimmee, FL 34746

Property at 936 Lake Berkley Dr, Kissimmee, FL 34746, 5 beds, 3 baths

$519,000

5 beds3 baths2,317 sq ft

936 Lake Berkley Dr, Kissimmee, FL 34746

Property at 581 Ocean Course Ave #581, Davenport, FL 33896, 2 beds, 2 baths

$264,900

2 beds2 baths1,388 sq ft

581 Ocean Course Ave #581, Davenport, FL 33896

Property at 451 Burma St, Kissimmee, FL 34747, 8 beds, 8 baths

$989,000

8 beds8 baths4,057 sq ft

451 Burma St, Kissimmee, FL 34747

Property at 917 Ocean Course Ave, Davenport, FL 33896, 8 beds, 5 baths

$740,000

8 beds5 baths3,915 sq ft

917 Ocean Course Ave, Davenport, FL 33896

Property at 4548 Orchard Grove Rd, Saint Cloud, FL 34772, 4 beds, 2 baths

$370,000

4 beds2 baths1,894 sq ft

4548 Orchard Grove Rd, Saint Cloud, FL 34772

Property at 3174 Feltrim Pl #201, Kissimmee, FL 34747, 3 beds, 2 baths

$223,000

3 beds2 baths1,269 sq ft

3174 Feltrim Pl #201, Kissimmee, FL 34747

Property at 7592 Bent Tree Loop, Harmony, FL 34773, 4 beds, 2 baths

$385,000

4 beds2 baths1,820 sq ft

7592 Bent Tree Loop, Harmony, FL 34773

Property at 2745 N Poinciana Blvd #63, Kissimmee, FL 34746, 3 beds, 2 baths

$225,000

3 beds2 baths1,287 sq ft

2745 N Poinciana Blvd #63, Kissimmee, FL 34746

$409,900

3 beds2 baths2,087 sq ft

5732 Iron Brand Rd, Saint Cloud, FL 34771

Property at 8876 Cabot Cliffs Dr, Davenport, FL 33896, 9 beds, 5 baths

$765,000

9 beds5 baths3,915 sq ft

8876 Cabot Cliffs Dr, Davenport, FL 33896

Property at 8876 Candy Palm Rd, Kissimmee, FL 34747, 6 beds, 5 baths

$509,000

6 beds5 baths3,291 sq ft

8876 Candy Palm Rd, Kissimmee, FL 34747

Property at 9075 Dogleg Dr, Davenport, FL 33896, 4 beds, 3 baths

$385,000

4 beds3 baths1,902 sq ft

9075 Dogleg Dr, Davenport, FL 33896

Property at 1314 Hyde St, Saint Cloud, FL 34771, 5 beds, 4.5 baths

$619,990

5 beds4.5 baths3,120 sq ft

1314 Hyde St, Saint Cloud, FL 34771

Property at 1580 Tempo Ln, Davenport, FL 33896, 6 beds, 5 baths

$535,500

6 beds5 baths3,291 sq ft

1580 Tempo Ln, Davenport, FL 33896

Property at 4327 Lighterknot Trce, Kissimmee, FL 34746, 4 beds, 3 baths

$434,000

4 beds3 baths2,581 sq ft

4327 Lighterknot Trce, Kissimmee, FL 34746

Property at 1315 Pine Island Dr N, Saint Cloud, FL 34771, 1 bed, 1.5 baths

$355,000

1 bed1.5 baths521 sq ft

1315 Pine Island Dr N, Saint Cloud, FL 34771

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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 3531 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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