Luxury homes for sale & real estate in Osceola County, FL

367 homes

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NEW 16 MINS AGO

ABOUT THIS HOME
Luxury Home 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

5,663 sq ft lot • Pool • Built 2022

NEW 14 MINS AGO

ABOUT THIS HOME
Luxury Home 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

5,663 sq ft lot • Pool • Built 2022

NEW 14 MINS AGO

ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
Welcome to this exceptional waterfront vacation home located in the heart of Storey Lake Resort at 4221 Paragraph Drive. Offering 8 bedrooms and 5 full bathrooms, this spacious and thoughtfully designed home is perfectly suited for large families, multi generational stays, or investors seeking a strong short term rental opportunity in one of Central Florida’s most in demand resort communities. The first floor welcomes you with an inviting foyer and an open concept layout designed for both comfort and entertaining. The gourmet kitchen features a large breakfast bar, ample cabinetry, and a generous pantry, all opening seamlessly to the dining area and great room. Sliding glass doors lea

$949,000

8 beds5 baths4,289 sq ft

4221 Paragraph Dr, Kissimmee, FL 34746

5,663 sq ft lot • Pool • Built 2021

OPEN SAT, 11AM TO 3PM

ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
Exquisite David Weekley Craftsman “The Grady” residence tucked away on a serene, tree-lined cul-de-sac and backing to a private conservation setting. This elegant 3-bedroom home, complemented by a spacious flex room/office and 2.5 baths, offers a rare blend of architectural charm and upscale modern living. The fully renovated kitchen and baths showcase premium finishes, including soft-close cabinetry, striking 42" upper cabinets, and designer accent lighting above the cabinets. An inviting eat-in kitchen flows effortlessly into a sun-drenched sunroom, creating an ideal space for refined entertaining or relaxed everyday living. Plantation shutters throughout and engineered w

$910,000

3 beds2.5 baths2,453 sq ft

1105 Banks Rose Ct, Kissimmee, FL 34747

Eat in kitchen • Premium finishes • Sun drenched sunroom

NEW 8 HRS AGO

ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
Absolutely stunning, fully renovated single-story home located on a premium corner lot in one of Celebration’s most desirable locations, offering park views and just a few blocks from Celebration Town Center. This exceptional property blends luxury, flexibility, and comfort, featuring a main residence, a private cabana, and a spacious garage apartment, along with three garages. One oversized garage is air-conditioned, making it ideal for a home office, creative studio, or content creation space. The main house features 3 bedrooms and 3 bathrooms and showcases a refined coastal-inspired design with engineered hardwood flooring and tile throughout. The impressive chef-inspired kitchen i

$2,100,000

5 beds5 baths4,347 sq ft

529 Greenbrier Ave, Kissimmee, FL 34747

Premium corner lot • Park views • Private cabana

Property at 350 Muirfield Loop, Reunion, FL 34747, 12 beds, 13 baths

$5,749,900

12 beds13 baths12,962 sq ft

350 Muirfield Loop, Reunion, FL 34747

Property at 2395 Rama Dr, Kissimmee, FL 34746, 15 beds, 16 baths

$1,650,000

15 beds16 baths6,249 sq ft

2395 Rama Dr, Kissimmee, FL 34746

Property at 2458 Dream Home Ct, Saint Cloud, FL 34772, 3 beds, 2.5 baths

$887,000

3 beds2.5 baths2,966 sq ft

2458 Dream Home Ct, Saint Cloud, FL 34772

Property at 4705 Kissimmee Park Rd, Saint Cloud, FL 34772, 3 beds, 2 baths

$975,000

3 beds2 baths1,559 sq ft

4705 Kissimmee Park Rd, Saint Cloud, FL 34772

Property at 7429 Gathering Ct, Reunion, FL 34747, 4 beds, 4 baths

$960,000

4 beds4 baths3,374 sq ft

7429 Gathering Ct, Reunion, FL 34747

Property at 7840 Palmilla Ct, Reunion, FL 34747, 8 beds, 9.5 baths

$4,490,000

8 beds9.5 baths7,928 sq ft

7840 Palmilla Ct, Reunion, FL 34747

Property at 908 Yew Ct, Kissimmee, FL 34747, 3 beds, 3 baths

$879,000

3 beds3 baths2,149 sq ft

908 Yew Ct, Kissimmee, FL 34747

Property at 1136 Celebration Ave, Kissimmee, FL 34747, 4 beds, 3.5 baths

$899,000

4 beds3.5 baths2,804 sq ft

1136 Celebration Ave, Kissimmee, FL 34747

Property at 310 Acadia Ln, Kissimmee, FL 34747, 7 beds, 8.5 baths

$4,900,000

7 beds8.5 baths8,216 sq ft

310 Acadia Ln, Kissimmee, FL 34747

Property at 1101 Banks Rose Ct, Kissimmee, FL 34747, 6 beds, 3.5 baths

$1,216,000

6 beds3.5 baths2,915 sq ft

1101 Banks Rose Ct, Kissimmee, FL 34747

Property at 839 Lake Evalyn Dr, Kissimmee, FL 34747, 5 beds, 3 baths

$979,000

5 beds3 baths2,196 sq ft

839 Lake Evalyn Dr, Kissimmee, FL 34747

Property at 103 Acadia Ter, Kissimmee, FL 34747, 6 beds, 5 baths

$2,299,000

6 beds5 baths4,679 sq ft

103 Acadia Ter, Kissimmee, FL 34747

Property at 1105 Watson Ct, Reunion, FL 34747, 9 beds, 9 baths

$1,770,000

9 beds9 baths5,591 sq ft

1105 Watson Ct, Reunion, FL 34747

Property at 1427 Fairview Cir, Reunion, FL 34747, 5 beds, 4.5 baths

$925,900

5 beds4.5 baths3,556 sq ft

1427 Fairview Cir, Reunion, FL 34747

Property at 2924 Penelope Loop, Kissimmee, FL 34746, 8 beds, 5 baths

$1,050,000

8 beds5 baths4,289 sq ft

2924 Penelope Loop, Kissimmee, FL 34746

Property at 751 Lasso Dr, Kissimmee, FL 34747, 10 beds, 10 baths

$949,000

10 beds10 baths4,733 sq ft

751 Lasso Dr, Kissimmee, FL 34747

Property at 834 Golden Bear Dr, Reunion, FL 34747, 5 beds, 5 baths

$1,249,000

5 beds5 baths3,530 sq ft

834 Golden Bear Dr, Reunion, FL 34747

Property at 7423 Sparkling Ct, Reunion, FL 34747, 7 beds, 8 baths

$1,200,000

7 beds8 baths3,938 sq ft

7423 Sparkling Ct, Reunion, FL 34747

Property at 2245 Bronco Dr, Saint Cloud, FL 34771, 5 beds, 5.5 baths

$1,160,000

5 beds5.5 baths3,439 sq ft

2245 Bronco Dr, Saint Cloud, FL 34771

Property at 416 Arbor Cir, Kissimmee, FL 34747, 6 beds, 5 baths

$2,399,000

6 beds5 baths5,266 sq ft

416 Arbor Cir, Kissimmee, FL 34747

Property at 1233 Grand Traverse Pkwy, Reunion, FL 34747, 9 beds, 9.5 baths

$1,975,000

9 beds9.5 baths5,853 sq ft

1233 Grand Traverse Pkwy, Reunion, FL 34747

Property at 2086 Blackfoot Trl, Saint Cloud, FL 34771, 5 beds, 5.5 baths

$875,000

5 beds5.5 baths4,546 sq ft

2086 Blackfoot Trl, Saint Cloud, FL 34771

Property at 460 Muirfield Loop, Reunion, FL 34747, 7 beds, 8.5 baths

$2,249,000

7 beds8.5 baths6,465 sq ft

460 Muirfield Loop, Reunion, FL 34747

Property at 294 Marcello Blvd, Kissimmee, FL 34746, 12 beds, 11.5 baths

$970,000

12 beds11.5 baths4,762 sq ft

294 Marcello Blvd, Kissimmee, FL 34746

Property at 4855 Lillian Black Rd, Saint Cloud, FL 34771, 5 beds, 3 baths

$850,000

5 beds3 baths2,982 sq ft

4855 Lillian Black Rd, Saint Cloud, FL 34771

Property at 2812 Sleeping Dragon Ln, Kissimmee, FL 34747, 8 beds, 8 baths

$1,995,000

8 beds8 baths6,140 sq ft

2812 Sleeping Dragon Ln, Kissimmee, FL 34747

Property at 4410 Mildred Bass Rd, Saint Cloud, FL 34772, 6 beds, 5.5 baths

$1,100,000

6 beds5.5 baths3,569 sq ft

4410 Mildred Bass Rd, Saint Cloud, FL 34772

Property at 1045 Jack Nicklaus Ct, Kissimmee, FL 34747, 8 beds, 9 baths

$2,495,000

8 beds9 baths5,625 sq ft

1045 Jack Nicklaus Ct, Kissimmee, FL 34747

Property at 7639 Wilmington Loop, Kissimmee, FL 34747, 11 beds, 10 baths

$986,000

11 beds10 baths4,707 sq ft

7639 Wilmington Loop, Kissimmee, FL 34747

Property at 502 Golfpark Dr, Kissimmee, FL 34747, 6 beds, 5.5 baths

$2,500,000

6 beds5.5 baths5,865 sq ft

502 Golfpark Dr, Kissimmee, FL 34747

Property at 4185 Cardinal Ln, Kissimmee, FL 34744, 2 beds, 2 baths

$1,200,000

2 beds2 baths1,188 sq ft

4185 Cardinal Ln, Kissimmee, FL 34744

Property at 1520 Canopy Oaks Ct, Saint Cloud, FL 34771, 5 beds, 3 baths

$1,495,000

5 beds3 baths3,591 sq ft

1520 Canopy Oaks Ct, Saint Cloud, FL 34771

Property at 4421 Reaves Rd, Kissimmee, FL 34746, 5 beds, 5.5 baths

$2,299,999

5 beds5.5 baths5,044 sq ft

4421 Reaves Rd, Kissimmee, FL 34746

Property at 7489 Estuary Lake Loop, Kissimmee, FL 34747, 7 beds, 5.5 baths

$1,895,000

7 beds5.5 baths5,236 sq ft

7489 Estuary Lake Loop, Kissimmee, FL 34747

Property at 7814 Loxahatchee Ct, Reunion, FL 34747, 6 beds, 5.5 baths

$1,375,000

6 beds5.5 baths4,260 sq ft

7814 Loxahatchee Ct, Reunion, FL 34747

Property at 801 Golden Bear Dr, Reunion, FL 34747, 6 beds, 5.5 baths

$1,509,700

6 beds5.5 baths3,428 sq ft

801 Golden Bear Dr, Reunion, FL 34747

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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.

Luxury Homes for Sale in Osceola County

There are currently 367 luxury homes 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, 511 homes have been sold in Osceola County. In addition to houses in Osceola County, there were also 716 condos, 1270 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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