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

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ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
Welcome to 4261 Twilight Trail, a stunning custom-built estate nestled on 5 private acres in the heart of Kissimmee. This property was thoughtfully designed with comfort, quality, and style in mind, featuring numerous upgrades throughout the home. Enjoy the perfect balance of space and privacy while still being close to shopping, dining, schools, and major highways. With its open layout, modern finishes, and expansive outdoor space, this home is ideal for families, entertaining, or those who simply want to enjoy the beauty of Florida living.

$1,100,000

3 beds2.5 baths3,129 sq ft

4261 Twilight Trl, Kissimmee, FL 34746

5.05 acre lot • 2 garage spots • Built 2007

ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
MOVE-IN READY 6-ACRE PRIVATE 3BD/2BA ESTATE WITH LOW DENSITY RESIDENTIAL (LDR) FLU is a rare gem offering the perfect blend of scenic tranquility, modern comforts, and unbeatable location—nestled just outside the booming LAKE NONA area, one of Central Florida’s most sought-after communities. Whether you're dreaming of a peaceful country lifestyle, an equestrian haven, or simply room to breathe, grow, and create—this property has it all. Featuring TWO SEPARATE GATED ENTRANCES—a private remote-controlled gate off Rambling Road and an additional gate through the Glenwood Subdivision—this estate offers security, privacy, and flexibility for multiple uses. The land

$869,999

3 beds2 baths1,973 sq ft

5365 Rambling Rd, Saint Cloud, FL 34771

Chicken coop • 6.08 acre lot • 2 parking spots

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
Step into the magical realm of this beautifully themed Disney-inspired income-generating property, located in the Champions Gate neighborhood of Davenport, Florida. The epic home features an impressive 9 bedrooms and 5 bathrooms, making it the perfect retreat for fun-seeking groups in search of an unforgettable vacation experience. With a 5-Star rating on Airbnb and Vrbo, this property brought in over $200K in short-term rental revenue 2024. And, investors will appreciate the financial potential of this property, showcasing an impressive 12.5% capitalization rate. With a strong history of rental income and high occupancy rates, this turn-key investment promises a consistent revenue stream.

$985,000

9 beds5 baths3,909 sq ft

1424 Wexford Way, Davenport, FL 33896

Professional arcade • Turn key investment • 6,098 sq ft lot

ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
Welcome to the gated community of Encore Resort at Reunion, this stunning 8-bedroom, 8.5-bathroom home is located close to major highways and theme parks. This amazing home offers open-format living, with plenty of natural lighting, dining, and kitchen space making it excellent for large family gatherings and holiday parties. The kitchen features granite countertops, stainless steel appliances, as well as a large island with plenty of space for dining. The downstairs master suite features a spacious bedroom and bathroom with a walk-in shower, tub, and dual sinks. The large second-floor area offers a large bonus room perfect for family activities. Each second-floor bedroom features an ensuit

$900,000

8 beds8.5 baths4,630 sq ft

7708 Fairfax Dr, Kissimmee, FL 34747

Gated community • Open-format living • Large island

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Osceola County, FL:
Quite Possibly the BEST LAKEFRONT LOT available in Osceola County, offering 11.3 Acres on Lake Tohopekaliga! The lake covers approximately 20,000 Acres and is about 42 miles in circumference, making ”Big” Lake Tohopekaliga the largest lake in Osceola County and one of the largest lakes in Florida! It boasts some of the best bass fishing in the country - in fact hosting the BassMasters’ tournament and consistently producing record breaking catches. This unique property has 480 linear feet of frontage on “Lake Toho, ” beautiful, mature oaks, cleared land, and is currently being used as agricultural - pastureland for cattle. Zoning is Mixed Use, making this partic

$3,785,500

4 beds1.5 baths2,437 sq ft

3650 Lake Tohopekaliga Rd, St Cloud, FL 34772

Lakefront lot • Mature oaks • Cleared land

Property at 3880 Sonoma Blvd, Kissimmee, FL 34741, 15 beds, 16 baths

$1,750,000

15 beds16 baths6,374 sq ft

3880 Sonoma Blvd, Kissimmee, FL 34741

Property at 2948 Scout St, Saint Cloud, FL 34771, 5 beds, 4.5 baths

$949,000

5 beds4.5 baths3,517 sq ft

2948 Scout St, Saint Cloud, FL 34771

Property at 7723 Graben St, Kissimmee, FL 34747, 9 beds, 8.5 baths

$860,000

9 beds8.5 baths4,630 sq ft

7723 Graben St, Kissimmee, FL 34747

Property at 7465 Gathering Loop, Reunion, FL 34747, 10 beds, 11 baths

$3,550,000

10 beds11 baths7,300 sq ft

7465 Gathering Loop, Reunion, FL 34747

Property at 4151 Boggy Creek Rd, Kissimmee, FL 34744, 5 beds, 3 baths

$2,800,000

5 beds3 baths3,652 sq ft

4151 Boggy Creek Rd, Kissimmee, FL 34744

Property at 2560 Shanti Dr, Kissimmee, FL 34746, 12 beds, 11.5 baths

$1,150,000

12 beds11.5 baths4,874 sq ft

2560 Shanti Dr, Kissimmee, FL 34746

Property at 2836 Simile St, Kissimmee, FL 34746, 9 beds, 5 baths

$1,100,000

9 beds5 baths4,289 sq ft

2836 Simile St, Kissimmee, FL 34746

Property at 4205 Paragraph Dr, Kissimmee, FL 34746, 7 beds, 5 baths

$1,150,000

7 beds5 baths3,994 sq ft

4205 Paragraph Dr, Kissimmee, FL 34746

Property at 942 Arbor Green Trl, Saint Cloud, FL 34771, 3 beds, 3 baths

$900,000

3 beds3 baths3,115 sq ft

942 Arbor Green Trl, Saint Cloud, FL 34771

Property at 7643 Wilmington Loop, Kissimmee, FL 34747, 11 beds, 10 baths

$974,000

11 beds10 baths4,707 sq ft

7643 Wilmington Loop, Kissimmee, FL 34747

Property at 824 Desert Mountain Ct, Reunion, FL 34747, 5 beds, 5.5 baths

$1,095,000

5 beds5.5 baths3,203 sq ft

824 Desert Mountain Ct, Reunion, FL 34747

Property at 2626 Calistoga Ave, Kissimmee, FL 34741, 10 beds, 8 baths

$850,000

10 beds8 baths4,275 sq ft

2626 Calistoga Ave, Kissimmee, FL 34741

Property at 4147 Boggy Creek Rd, Kissimmee, FL 34744, 4 beds, 3 baths

$1,850,000

4 beds3 baths2,932 sq ft

4147 Boggy Creek Rd, Kissimmee, FL 34744

Property at 3667 Malawi Trl, Saint Cloud, FL 34772, 5 beds, 3 baths

$893,231

5 beds3 baths2,929 sq ft

3667 Malawi Trl, Saint Cloud, FL 34772

Property at 7824 Loxahatchee Ct, Reunion, FL 34747, 5 beds, 5.5 baths

$899,000

5 beds5.5 baths3,328 sq ft

7824 Loxahatchee Ct, Reunion, FL 34747

Property at 7736 Graben St, Kissimmee, FL 34747, 9 beds, 8.5 baths

$1,009,000

9 beds8.5 baths4,630 sq ft

7736 Graben St, Kissimmee, FL 34747

Property at 5100 Helen Ct, Saint Cloud, FL 34772, 4 beds, 3.5 baths

$1,590,000

4 beds3.5 baths3,574 sq ft

5100 Helen Ct, Saint Cloud, FL 34772

Property at 1003 Jack Nicklaus Ct, Kissimmee, FL 34747, 6 beds, 6.5 baths

$1,820,000

6 beds6.5 baths4,588 sq ft

1003 Jack Nicklaus Ct, Kissimmee, FL 34747

Property at 418 Marcello Blvd, Kissimmee, FL 34746, 12 beds, 11.5 baths

$880,000

12 beds11.5 baths4,762 sq ft

418 Marcello Blvd, Kissimmee, FL 34746

Property at 733 Desert Mountain Ct, Reunion, FL 34747, 5 beds, 4 baths

$1,175,000

5 beds4 baths3,131 sq ft

733 Desert Mountain Ct, Reunion, FL 34747

Property at 7807 Loxahatchee Ct, Reunion, FL 34747, 4 beds, 6 baths

$2,200,000

4 beds6 baths4,498 sq ft

7807 Loxahatchee Ct, Reunion, FL 34747

Property at 1888 Druliner Rd, Saint Cloud, FL 34771, 2 beds, 1 bath

$1,350,000

2 beds1 bath728 sq ft

1888 Druliner Rd, Saint Cloud, FL 34771

Property at 2800 Simile St, Kissimmee, FL 34746, 9 beds, 5 baths

$920,000

9 beds5 baths4,289 sq ft

2800 Simile St, Kissimmee, FL 34746

Property at 1169 Castle Pines Ct, Reunion, FL 34747, 5 beds, 6 baths

$995,000

5 beds6 baths3,753 sq ft

1169 Castle Pines Ct, Reunion, FL 34747

Property at 7388 Gathering Ct, Reunion, FL 34747, 5 beds, 4.5 baths

$1,125,000

5 beds4.5 baths4,197 sq ft

7388 Gathering Ct, Reunion, FL 34747

Property at 2816 Simile St, Kissimmee, FL 34746, 10 beds, 5 baths

$1,040,000

10 beds5 baths4,289 sq ft

2816 Simile St, Kissimmee, FL 34746

Property at 7600 Mackinaw Ln, Kissimmee, FL 34747, 8 beds, 6.5 baths

$1,400,000

8 beds6.5 baths3,612 sq ft

7600 Mackinaw Ln, Kissimmee, FL 34747

Property at 1002 Jack Nicklaus Ct, Kissimmee, FL 34747, 8 beds, 10 baths

$2,495,000

8 beds10 baths5,590 sq ft

1002 Jack Nicklaus Ct, Kissimmee, FL 34747

Property at 6043 S Orange Blossom Trl, Davenport, FL 33896, 3 beds, 1.5 baths

$2,300,000

3 beds1.5 baths1,102 sq ft

6043 S Orange Blossom Trl, Davenport, FL 33896

Property at 9043 Sunshine Ridge Loop, Kissimmee, FL 34747, 9 beds, 6.5 baths

$865,000

9 beds6.5 baths4,363 sq ft

9043 Sunshine Ridge Loop, Kissimmee, FL 34747

Property at 7519 Marker Ave, Kissimmee, FL 34747, 10 beds, 10 baths

$953,900

10 beds10 baths4,683 sq ft

7519 Marker Ave, Kissimmee, 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 2537 Shanti Dr, Kissimmee, FL 34746, 9 beds, 7 baths

$875,000

9 beds7 baths4,267 sq ft

2537 Shanti Dr, Kissimmee, FL 34746

Property at 1466 Moon Valley Dr, Davenport, FL 33896, 9 beds, 5 baths

$999,900

9 beds5 baths3,909 sq ft

1466 Moon Valley Dr, Davenport, FL 33896

Property at 1314 Birdie Way, Davenport, FL 33896, 9 beds, 5 baths

$899,990

9 beds5 baths3,909 sq ft

1314 Birdie Way, Davenport, FL 33896

Property at 1004 Castle Pines Ct, Reunion, FL 34747, 6 beds, 5.5 baths

$1,140,000

6 beds5.5 baths3,203 sq ft

1004 Castle Pines Ct, Reunion, FL 34747

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Based on information submitted to the MLS GRID as of Mon Dec 01 2025. 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 394 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 104 days and receive 2 offers. This map is refreshed with the newest listings in Osceola County every 15 minutes.

In the past month, 709 homes have been sold in Osceola County. In addition to houses in Osceola County, there were also 722 condos, 1233 townhouses, and 16 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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