Homes with Pools for Sale in Osceola County, FL

5,263 homes

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NEW 1 HR AGO

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to this impressive waterfront vacation home located in the heart of Storey Lake Resort at 2956 Penelope Loop in Kissimmee. Offering 8 bedrooms and 5 full bathrooms, this spacious home is designed for both memorable stays and strong rental performance in one of Central Florida’s most sought after short term rental communities. The first floor welcomes you with a bright entry foyer and an open, functional layout ideal for entertaining large groups. The gourmet kitchen features ample cabinetry, a breakfast bar, and a large pantry, all flowing seamlessly into the dining area and expansive great room. Multiple bedrooms on the main level provide flexibility and convenience, includin

$949,000

8 beds5 baths4,289 sq ft

2956 Penelope Loop, Kissimmee, FL 34746

Gourmet kitchen • Dedicated game room • Covered patio

NEW 1 HR AGO

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to an exceptional waterfront home in the heart of Storey Lake Resort, located at 4213 Paragraph Dr, Kissimmee, FL 34746. This expansive 8 bedroom, 5 bathroom property was designed to deliver both unforgettable vacations and strong rental performance, making it a standout opportunity for buyers seeking a proven short term rental home. The first floor welcomes you with an inviting foyer and a thoughtfully designed layout that flows seamlessly for large groups. Highlights include a spacious primary suite with a private en suite bathroom, an additional guest bedroom and full bathroom, and a large game room perfect for entertaining. The open concept living space features a gourmet kitche

$949,000

8 beds5 baths4,289 sq ft

4213 Paragprah Dr, Kissimmee, FL 34746

Waterfront home • Gourmet kitchen • Covered patio

NEW 1 HR AGO3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
NEW & IMPROVED!! * New Roof in 2018, New AC 2021, New Water Heater 2022! Also, Brand New Luxury Vinyl Plank flooring and carpet installed throughout the entire property AND Newly installed closets in guest bedrooms for added convenience! Welcome to this stunning 4 bedroom, 2 1/2 bathroom home in Crepe Myrtle Cove At Crescent Lakes with a fully fenced in Spacious backyard, blending both convenience and charm. Upon entering, you'll be greeted by a spacious open floor plan with high vaulted ceilings and plenty of natural lighting. The main floor flows seamlessly from the bonus living room into the formal dining area and kitchen where you'll notice the large family room next to the slidi

$415,000

4 beds2.5 baths2,847 sq ft

5456 Crepe Myrtle Cir, Kissimmee, FL 34758

Open floor plan • Spacious backyard • New water heater

NEW 5 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to this beautiful POOL HOME retreat in the heart of one of Kissimmee’s well-established communities. With NO HOA and NO CDD, this property offers rare flexibility and freedom, whether you're looking for a primary residence, a vacation getaway, or a high-earning SHORT-TERM RENTAL, AIRBNB, or long-term rental. The interior has been thoughtfully redesigned with modern finishes, an open layout, and an emphasis on light, flow, and comfort. Updated fixtures, contemporary design touches, and fresh surfaces throughout provide a move-in-ready experience. This FIVE BEDROOM residence features an inviting living space that seamlessly connects to the kitchen and dining areas, creating an i

$439,900

5 beds3 baths1,864 sq ft

1653 Oak Hill Trl, Kissimmee, FL 34747

No cdd • Pool home • Short-term rental

NEW 1 HR AGO3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Turnkey 3-Bedroom Home Near Disney – Fully Furnished! Located in the desirable, guard-gated Windsor Palms Resort community, this well-kept 3-bedroom, 2-bath pool home residence is just minutes from Walt Disney World and major attractions. Offered fully furnished and ready for immediate occupancy, the home is ideal as a full-time residence, vacation retreat, or income-producing property with both short-term and long-term rental options. Residents and guests enjoy access to outstanding resort amenities, including a clubhouse, community pool, fitness center, and more. A fantastic opportunity for personal use or investment in one of the area’s most popular resort communities. Additi

$399,999

3 beds2 baths1,664 sq ft

8204 Fan Palm Way, Kissimmee, FL 34747

Fitness center • Community pool • 6,055 sq ft lot

Property at Undisclosed address, Reunion, FL 34747, 3 beds, 2.5 baths

$340,000

3 beds2.5 baths1,704 sq ft

Undisclosed address, Reunion, FL 34747

Property at 4221 Paragraph Dr, Kissimmee, FL 34746, 8 beds, 5 baths

$949,000

8 beds5 baths4,289 sq ft

4221 Paragraph Dr, Kissimmee, FL 34746

Property at 56 E 56 Peterlee Ct. Ct, Kissimmee, FL 34758, 3 beds, 2 baths

$294,999

3 beds2 baths1,304 sq ft

56 E 56 Peterlee Ct. Ct, Kissimmee, FL 34758

Property at 2798 Club Cortile Cir Unit A, Kissimmee, FL 34746, 3 beds, 2 baths

$244,900

3 beds2 baths1,202 sq ft

2798 Club Cortile Cir Unit A, Kissimmee, FL 34746

Property at 1105 Banks Rose Ct, Kissimmee, FL 34747, 3 beds, 2.5 baths

$910,000

3 beds2.5 baths2,453 sq ft

1105 Banks Rose Ct, Kissimmee, FL 34747

Property at 4686 Tribute Trl #4686, Kissimmee, FL 34746, 3 beds, 2.5 baths

$385,000

3 beds2.5 baths1,797 sq ft

4686 Tribute Trl #4686, Kissimmee, FL 34746

Property at 6114 Waterfield Way, Saint Cloud, FL 34771, 4 beds, 2.5 baths

$485,000

4 beds2.5 baths2,419 sq ft

6114 Waterfield Way, Saint Cloud, FL 34771

Property at 412 Tarpon St, Kissimmee, FL 34744, 3 beds, 2 baths

$345,000

3 beds2 baths1,341 sq ft

412 Tarpon St, Kissimmee, FL 34744

Property at 1490 Woodmont Blvd, Kissimmee, FL 34746, 5 beds, 2.5 baths

$469,900

5 beds2.5 baths2,060 sq ft

1490 Woodmont Blvd, Kissimmee, FL 34746

Property at 6805 Sundrop St, Harmony, FL 34773, 3 beds, 2 baths

$349,900

3 beds2 baths1,617 sq ft

6805 Sundrop St, Harmony, FL 34773

Property at 4899 Sparrow Dr, Saint Cloud, FL 34772, 4 beds, 2.5 baths

$630,000

4 beds2.5 baths2,498 sq ft

4899 Sparrow Dr, Saint Cloud, FL 34772

Property at 8869 Rhodes St, Kissimmee, FL 34747, 6 beds, 4.5 baths

$610,000

6 beds4.5 baths3,142 sq ft

8869 Rhodes St, Kissimmee, FL 34747

Property at 337 Bogey Dr, Davenport, FL 33896, 4 beds, 3.5 baths

$389,900

4 beds3.5 baths1,954 sq ft

337 Bogey Dr, Davenport, FL 33896

Property at 5271 Brydon Woods Cir, Saint Cloud, FL 34771, 5 beds, 3 baths

$530,000

5 beds3 baths2,677 sq ft

5271 Brydon Woods Cir, Saint Cloud, FL 34771

Property at 9092 Sommerset Hills Dr, Davenport, FL 33896, 7 beds, 6 baths

$695,000

7 beds6 baths3,843 sq ft

9092 Sommerset Hills Dr, Davenport, FL 33896

Property at 529 Greenbrier Ave, Kissimmee, FL 34747, 5 beds, 5 baths

$2,100,000

5 beds5 baths4,347 sq ft

529 Greenbrier Ave, Kissimmee, FL 34747

Property at 304 Cocoa Ct, Kissimmee, FL 34758, 4 beds, 2.5 baths

$360,000

4 beds2.5 baths2,844 sq ft

304 Cocoa Ct, Kissimmee, FL 34758

Property at 2045 Rankin St, Kindred, FL 34744, 4 beds, 3 baths

$524,900

4 beds3 baths2,142 sq ft

2045 Rankin St, Kindred, FL 34744

Property at 5322 Royal Pt, Kissimmee, FL 34746, 5 beds, 2.5 baths

$528,000

5 beds2.5 baths2,615 sq ft

5322 Royal Pt, Kissimmee, FL 34746

Property at 5024 Shady Pines Dr, Saint Cloud, FL 34772, 4 beds, 2 baths

$585,000

4 beds2 baths2,644 sq ft

5024 Shady Pines Dr, Saint Cloud, FL 34772

Property at 1797 Red Canyon Dr, Kindred, FL 34744, 3 beds, 2.5 baths

$329,900

3 beds2.5 baths1,870 sq ft

1797 Red Canyon Dr, Kindred, FL 34744

Property at 3680 Circle Hook St, Kissimmee, FL 34746, 3 beds, 2.5 baths

$259,900

3 beds2.5 baths1,365 sq ft

3680 Circle Hook St, Kissimmee, FL 34746

Property at 8007 Acadia Estates Ct, Kissimmee, FL 34747, 6 beds, 6.5 baths

$599,900

6 beds6.5 baths3,366 sq ft

8007 Acadia Estates Ct, Kissimmee, FL 34747

Property at 4760 Kings Castle Cir, Kissimmee, FL 34746, 5 beds, 5 baths

$625,900

5 beds5 baths3,081 sq ft

4760 Kings Castle Cir, Kissimmee, FL 34746

Property at 4321 Rummell Rd, Saint Cloud, FL 34769, 3 beds, 2 baths

$670,700

3 beds2 baths2,252 sq ft

4321 Rummell Rd, Saint Cloud, FL 34769

Property at 318 Plumwood Cir, Kissimmee, FL 34743, 3 beds, 2 baths

$324,900

3 beds2 baths1,326 sq ft

318 Plumwood Cir, Kissimmee, FL 34743

Property at 2761 Eagle Glen Cir, Kissimmee, FL 34746, 4 beds, 2 baths

$365,000

4 beds2 baths1,952 sq ft

2761 Eagle Glen Cir, Kissimmee, FL 34746

Property at 547 Brighton Ct, Kissimmee, FL 34758, 4 beds, 2.5 baths

$350,000

4 beds2.5 baths2,691 sq ft

547 Brighton Ct, Kissimmee, FL 34758

Property at 1386 Olympic Club Blvd, Champions Gate, FL 33896, 4 beds, 3 baths

$599,000

4 beds3 baths2,287 sq ft

1386 Olympic Club Blvd, Champions Gate, FL 33896

Property at 5114 Sage Way, Kissimmee, FL 34758, 4 beds, 2 baths

$340,000

4 beds2 baths1,731 sq ft

5114 Sage Way, Kissimmee, FL 34758

Property at 1396 Palmetto Dunes St, Davenport, FL 33896, 4 beds, 3 baths

$499,000

4 beds3 baths2,381 sq ft

1396 Palmetto Dunes St, Davenport, FL 33896

Property at 107 Grinnell Pl, Kissimmee, FL 34747, 4 beds, 2.5 baths

$699,900

4 beds2.5 baths2,035 sq ft

107 Grinnell Pl, Kissimmee, FL 34747

Property at 4902 Monarch Ln, Kissimmee, FL 34746, 4 beds, 2.5 baths

$404,900

4 beds2.5 baths1,874 sq ft

4902 Monarch Ln, Kissimmee, FL 34746

Property at 8023 Acadia Estates Ct, Kissimmee, FL 34747, 7 beds, 6.5 baths

$595,000

7 beds6.5 baths2,884 sq ft

8023 Acadia Estates Ct, Kissimmee, FL 34747

Property at 1801 Eastern Ave, Saint Cloud, FL 34769, 3 beds, 2 baths

$475,000

3 beds2 baths2,027 sq ft

1801 Eastern Ave, Saint Cloud, FL 34769

Property at 4165 Key Colony Pl, Kissimmee, FL 34746, 4 beds, 2.5 baths

$385,000

4 beds2.5 baths2,156 sq ft

4165 Key Colony Pl, Kissimmee, FL 34746

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Based on information submitted to the MLS GRID as of Fri Jan 02 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 5263 homes with pools for sale in Osceola County at a median listing price of $420K. 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 107 days and receive 2 offers. This map is refreshed with the newest listings in Osceola County every 15 minutes.

In the past month, 509 homes have been sold in Osceola County. In addition to houses in Osceola County, there were also 717 condos, 1269 townhouses, and 15 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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