C21okeechobee.com Search Results

$699,000

Welcome to an exceptional opportunity in Windsor Hills Resort, one of Central Florida's premier vacation home communities just minutes from Walt Disney World. This beautifully renovated and fully furnished 6-bedroom, 4-bath single-family pool home offers 2,812 square feet of thoughtfully designed living space, combining resort-style living with outstanding vacation-rental appeal. Step inside to a bright, spacious floor plan featuring two primary suites, stylish finishes, stone countertops, and inviting living and dining spaces designed for entertaining and relaxing. The home's professionally themed spaces elevate the guest experience, including an impressive Avengers-inspired game room and Mickey, Toy Story, and Star Wars-themed bedrooms that create a memorable Central Florida getaway. Outdoors, enjoy your own private screened pool and spa with a generous pool deck, the perfect setting to relax in the Florida sunshine after a day at the theme parks. Located within the 24-hour guard-gated Windsor Hills community, owners and guests enjoy an exceptional collection of resort amenities including a spectacular water park, resort-style swimming pool and hot tub, clubhouse, fitness center, movie theater, game room, playground, tennis and basketball courts, volleyball, putting green, dog park, and on-site Marketplace & Grill. Windsor Hills is an established vacation rental community offering an outstanding location near Walt Disney World and convenient access to Central Florida's world-famous attractions, dining, shopping, and entertainment. Whether you are searching for a luxurious Florida vacation residence, a second home, or a property positioned for the short-term rental market, this turnkey Windsor Hills home delivers the location, space, amenities, and guest appeal today's buyers are looking for. Schedule your private showing and experience everything this exceptional property has to provide.

6 Beds ⋅ 4 Baths ⋅ O6435446 MLS

Welcome to an exceptional opportunity in Windsor Hills Resort, one of Central Florida's premier vacation home communities just minutes from Walt Disney World. This beautifully renovated and fully furnished 6-bedroom, 4-bath single-family pool home offers 2,812 square feet of thoughtfully designed living space, combining resort-style living with outstanding vacation-rental appeal. Step inside to a bright, spacious floor plan featuring two primary suites, stylish finishes, stone countertops, and inviting living and dining spaces designed for entertaining and relaxing. The home's professionally themed spaces elevate the guest experience, including an impressive Avengers-inspired game room and Mickey, Toy Story, and Star Wars-themed bedrooms that create a memorable Central Florida getaway. Outdoors, enjoy your own private screened pool and spa with a generous pool deck, the perfect setting to relax in the Florida sunshine after a day at the theme parks. Located within the 24-hour guard-gated Windsor Hills community, owners and guests enjoy an exceptional collection of resort amenities including a spectacular water park, resort-style swimming pool and hot tub, clubhouse, fitness center, movie theater, game room, playground, tennis and basketball courts, volleyball, putting green, dog park, and on-site Marketplace & Grill. Windsor Hills is an established vacation rental community offering an outstanding location near Walt Disney World and convenient access to Central Florida's world-famous attractions, dining, shopping, and entertainment. Whether you are searching for a luxurious Florida vacation residence, a second home, or a property positioned for the short-term rental market, this turnkey Windsor Hills home delivers the location, space, amenities, and guest appeal today's buyers are looking for. Schedule your private showing and experience everything this exceptional property has to provide.

7772 Basnett Circle, Kissimmee

Listing courtesy of WRA BUSINESS & REAL ESTATE. 407-512-1008

$629,900

Whether you're looking for an income-producing vacation rental or a personal retreat, this 5-bedroom, 5-bath home in the highly desirable gated community of Windsor Hills is an excellent opportunity. The kitchen is positioned at the front of the home and overlooks the formal dining area, creating a welcoming space for family meals and entertaining. The living room is located at the rear of the home and opens to the screened-in pool deck, offering a relaxing space to enjoy the Florida sunshine. Three bedrooms including the primary are conveniently located on the first floor, with two sharing a jack and jill bathroom set up, while the remaining bedrooms and bathrooms are upstairs, providing comfort and privacy for guests. The garage has been converted into a fun games room with pool and foosball tables, adding extra appeal for renters. Windsor Hills is one of the closest resorts to Disney and features outstanding amenities, including a resort-style pool with water slides, clubhouse, fitness center, and sports courts. Ideal for short-term rental investment, second home, or full-time residence.

5 Beds ⋅ 5 Baths ⋅ O6434446 MLS

Whether you're looking for an income-producing vacation rental or a personal retreat, this 5-bedroom, 5-bath home in the highly desirable gated community of Windsor Hills is an excellent opportunity. The kitchen is positioned at the front of the home and overlooks the formal dining area, creating a welcoming space for family meals and entertaining. The living room is located at the rear of the home and opens to the screened-in pool deck, offering a relaxing space to enjoy the Florida sunshine. Three bedrooms including the primary are conveniently located on the first floor, with two sharing a jack and jill bathroom set up, while the remaining bedrooms and bathrooms are upstairs, providing comfort and privacy for guests. The garage has been converted into a fun games room with pool and foosball tables, adding extra appeal for renters. Windsor Hills is one of the closest resorts to Disney and features outstanding amenities, including a resort-style pool with water slides, clubhouse, fitness center, and sports courts. Ideal for short-term rental investment, second home, or full-time residence.

7795 Basnett Circle, Kissimmee

Listing courtesy of THE AGENCY FL. 407-335-4119

$659,000

Welcome to 7765 Tosteth Street, a beautifully appointed vacation home in the heart of Windsor Hills Resort — Orlando's premier gated short-term rental community, just minutes from Walt Disney World. This spacious 6-bedroom, 4-bathroom pool home offers 2,812 sq ft of thoughtfully designed living space, perfect for large groups looking for comfort, privacy, and resort-style amenities. The open-concept main floor features a generous living and dining area, a fully equipped kitchen, a first-floor bedroom with full bath — ideal for guests who prefer single-level living — a dedicated laundry room, and a game room for added entertainment. Step outside to your private screened pool with heated spa, surrounded by a covered patio and deck — the perfect setting for relaxing afternoons under the Florida sun. Windsor Hills Resort amenities include a clubhouse, resort-style community pool, waterpark, fitness center, game room, tennis courts, and 24-hour gated security — everything your guests need without ever leaving the community. Whether you're looking for a turn-key investment property with strong short-term rental potential or a private family retreat steps from the magic of Orlando, 7765 Tosteth Street is ready to deliver. Offered fully furnished and ready to generate income from day one.

6 Beds ⋅ 4 Baths ⋅ O6423586 MLS

Welcome to 7765 Tosteth Street, a beautifully appointed vacation home in the heart of Windsor Hills Resort — Orlando's premier gated short-term rental community, just minutes from Walt Disney World. This spacious 6-bedroom, 4-bathroom pool home offers 2,812 sq ft of thoughtfully designed living space, perfect for large groups looking for comfort, privacy, and resort-style amenities. The open-concept main floor features a generous living and dining area, a fully equipped kitchen, a first-floor bedroom with full bath — ideal for guests who prefer single-level living — a dedicated laundry room, and a game room for added entertainment. Step outside to your private screened pool with heated spa, surrounded by a covered patio and deck — the perfect setting for relaxing afternoons under the Florida sun. Windsor Hills Resort amenities include a clubhouse, resort-style community pool, waterpark, fitness center, game room, tennis courts, and 24-hour gated security — everything your guests need without ever leaving the community. Whether you're looking for a turn-key investment property with strong short-term rental potential or a private family retreat steps from the magic of Orlando, 7765 Tosteth Street is ready to deliver. Offered fully furnished and ready to generate income from day one.

7765 Tosteth Street, Kissimmee

Listing courtesy of FLORIDA 360 REALTY LLC. 954-245-9346

$609,000

This beautifully maintained 5-bedroom, 5-bath home in the 5-Star Windsor Hills Resort is an income-producing short-term vacation rental located just minutes from Walt Disney World. Highly sought after for its open floorplan, this property features the resort’s most desirable 5-bedroom layout, offering exceptional flow and comfort for large families and vacationing groups. The home immediately stands out thanks to extensive mechanical and interior upgrades, including a 2022 roof with 30-year architectural shingles, a 2023 saltwater pool system that is both low-cost and low-maintenance, a 2023 WiFi-controlled pool heater, a brand-new 2026 water heater with WiFi capability, new toilets added in 2026, and dual HVAC systems with major components replaced in 2016 and newer coils added within the last two years. Nest thermostats enhance efficiency, while upgraded bath vanities with solid-surface counters and wood-laminate hickory flooring in all bedrooms elevate the home’s interior appeal, durability, and rental desirability. For investors, the seller is willing to transfer any future bookings, allowing for immediate income continuity. Inside, the open main level features a spacious main dining area, a separate breakfast room, kitchen bar seating, granite countertops, stainless steel appliances, and a large living area ideal for gathering. Two first-floor ensuite bedrooms and an additional queen bedroom with adjacent bath provide convenient main-level living, while the second floor offers two Disney-themed junior suites, each with its own bathroom—an instant favorite among vacationing families. The converted garage game room with air hockey and pool tables adds to the home’s strong guest appeal. Outside, the screened lanai features a private heated saltwater pool and spa surrounded by privacy screening and a mature hedge, creating a secluded retreat perfect for relaxing after a day at the parks. Windsor Hills Resort remains one of Central Florida’s most desirable vacation rental communities, offering a clubhouse with lagoon-style pool, tennis courts, racquetball court, basketball court, marketplace, theater, game room, and fitness center, along with playgrounds, putting greens, and 24-hour guarded security. It is a prime vacation location due to its proximity to Disney, making this home an exceptional opportunity for buyers seeking a reliable, well-maintained, income-generating vacation property.

5 Beds ⋅ 5 Baths ⋅ O6413930 MLS

This beautifully maintained 5-bedroom, 5-bath home in the 5-Star Windsor Hills Resort is an income-producing short-term vacation rental located just minutes from Walt Disney World. Highly sought after for its open floorplan, this property features the resort’s most desirable 5-bedroom layout, offering exceptional flow and comfort for large families and vacationing groups. The home immediately stands out thanks to extensive mechanical and interior upgrades, including a 2022 roof with 30-year architectural shingles, a 2023 saltwater pool system that is both low-cost and low-maintenance, a 2023 WiFi-controlled pool heater, a brand-new 2026 water heater with WiFi capability, new toilets added in 2026, and dual HVAC systems with major components replaced in 2016 and newer coils added within the last two years. Nest thermostats enhance efficiency, while upgraded bath vanities with solid-surface counters and wood-laminate hickory flooring in all bedrooms elevate the home’s interior appeal, durability, and rental desirability. For investors, the seller is willing to transfer any future bookings, allowing for immediate income continuity. Inside, the open main level features a spacious main dining area, a separate breakfast room, kitchen bar seating, granite countertops, stainless steel appliances, and a large living area ideal for gathering. Two first-floor ensuite bedrooms and an additional queen bedroom with adjacent bath provide convenient main-level living, while the second floor offers two Disney-themed junior suites, each with its own bathroom—an instant favorite among vacationing families. The converted garage game room with air hockey and pool tables adds to the home’s strong guest appeal. Outside, the screened lanai features a private heated saltwater pool and spa surrounded by privacy screening and a mature hedge, creating a secluded retreat perfect for relaxing after a day at the parks. Windsor Hills Resort remains one of Central Florida’s most desirable vacation rental communities, offering a clubhouse with lagoon-style pool, tennis courts, racquetball court, basketball court, marketplace, theater, game room, and fitness center, along with playgrounds, putting greens, and 24-hour guarded security. It is a prime vacation location due to its proximity to Disney, making this home an exceptional opportunity for buyers seeking a reliable, well-maintained, income-generating vacation property.

Kissimmee

Listing courtesy of IN TOUCH REAL ESTATE LLC. 800-515-0321

$649,000

Strong booking activity through the end of 2026!! Welcome to your ultimate vacation getaway-fully renovated in 2025 and featuring a brand-new roof (2025), all on a prime corner lot just 5 miles from Walt Disney World. This beautifully upgraded 5-bedroom pool and spa home is designed for comfort, fun, and strong short-term rental appeal, complete with an impressive converted garage game room for unforgettable guest experiences. Recent upgrades include two new water heaters (2025), exterior painting (2025) updated kitchen and all five bathroom vanities (2025), granite countertops in every bathroom, and new commercial-grade carpet installed in 2025, new furniture, and many more-making this home truly move-in ready. ACs were replaced in 2024 and 2022. Themed living takes center stage with 7 immersive themes throughout the home. The two primary suites feature How to Train Your Dragon and Avengers themes. The main-level bedroom is Star Wars, while the upstairs bedrooms are Toy Story and Mickey Mouse. Sleeping arrangements include 3 king beds and 4 twin beds. The garage is transformed into a Harry Potter-themed game room with foosball, air hockey, and a pool table, while the dining room brings the fun with a Super Nintendo World theme. Located in the highly sought-after, guard-gated Windsor Hills community, owners and guests enjoy top-tier resort amenities including a lagoon-style pool, water park with slides, fitness center, movie theater, arcade, bar, convenience store, playgrounds, and sports courts-all just minutes from Central Florida's world-class attractions. Selller is a licensed real estate agent.

5 Beds ⋅ 5 Baths ⋅ 11629998 MLS

Strong booking activity through the end of 2026!! Welcome to your ultimate vacation getaway-fully renovated in 2025 and featuring a brand-new roof (2025), all on a prime corner lot just 5 miles from Walt Disney World. This beautifully upgraded 5-bedroom pool and spa home is designed for comfort, fun, and strong short-term rental appeal, complete with an impressive converted garage game room for unforgettable guest experiences. Recent upgrades include two new water heaters (2025), exterior painting (2025) updated kitchen and all five bathroom vanities (2025), granite countertops in every bathroom, and new commercial-grade carpet installed in 2025, new furniture, and many more-making this home truly move-in ready. ACs were replaced in 2024 and 2022. Themed living takes center stage with 7 immersive themes throughout the home. The two primary suites feature How to Train Your Dragon and Avengers themes. The main-level bedroom is Star Wars, while the upstairs bedrooms are Toy Story and Mickey Mouse. Sleeping arrangements include 3 king beds and 4 twin beds. The garage is transformed into a Harry Potter-themed game room with foosball, air hockey, and a pool table, while the dining room brings the fun with a Super Nintendo World theme. Located in the highly sought-after, guard-gated Windsor Hills community, owners and guests enjoy top-tier resort amenities including a lagoon-style pool, water park with slides, fitness center, movie theater, arcade, bar, convenience store, playgrounds, and sports courts-all just minutes from Central Florida's world-class attractions. Selller is a licensed real estate agent.

7788 Basnett Circle, Kissimmee

Listing courtesy of Mike Chen, P.A with La Rosa Realty Llc

$649,000

Strong booking activity through the end of 2026!! Welcome to your ultimate vacation getaway—fully renovated in 2025 and featuring a brand-new roof (2025), all on a prime corner lot just 5 miles from Walt Disney World. This beautifully upgraded 5-bedroom pool and spa home is designed for comfort, fun, and strong short-term rental appeal, complete with an impressive converted garage game room for unforgettable guest experiences. Recent upgrades include two new water heaters (2025), exterior painting (2025) updated kitchen and all five bathroom vanities (2025), granite countertops in every bathroom, and new commercial-grade carpet installed in 2025, new furniture, and many more—making this home truly move-in ready. ACs were replaced in 2024 and 2022. Themed living takes center stage with 7 immersive themes throughout the home. The two primary suites feature How to Train Your Dragon and Avengers themes. The main-level bedroom is Star Wars, while the upstairs bedrooms are Toy Story and Mickey Mouse. Sleeping arrangements include 3 king beds and 4 twin beds. The garage is transformed into a Harry Potter–themed game room with foosball, air hockey, and a pool table, while the dining room brings the fun with a Super Nintendo World theme. Located in the highly sought-after, guard-gated Windsor Hills community, owners and guests enjoy top-tier resort amenities including a lagoon-style pool, water park with slides, fitness center, movie theater, arcade, bar, convenience store, playgrounds, and sports courts—all just minutes from Central Florida’s world-class attractions. Selller is a licensed real estate agent.

5 Beds ⋅ 5 Baths ⋅ O6371195 MLS

Strong booking activity through the end of 2026!! Welcome to your ultimate vacation getaway—fully renovated in 2025 and featuring a brand-new roof (2025), all on a prime corner lot just 5 miles from Walt Disney World. This beautifully upgraded 5-bedroom pool and spa home is designed for comfort, fun, and strong short-term rental appeal, complete with an impressive converted garage game room for unforgettable guest experiences. Recent upgrades include two new water heaters (2025), exterior painting (2025) updated kitchen and all five bathroom vanities (2025), granite countertops in every bathroom, and new commercial-grade carpet installed in 2025, new furniture, and many more—making this home truly move-in ready. ACs were replaced in 2024 and 2022. Themed living takes center stage with 7 immersive themes throughout the home. The two primary suites feature How to Train Your Dragon and Avengers themes. The main-level bedroom is Star Wars, while the upstairs bedrooms are Toy Story and Mickey Mouse. Sleeping arrangements include 3 king beds and 4 twin beds. The garage is transformed into a Harry Potter–themed game room with foosball, air hockey, and a pool table, while the dining room brings the fun with a Super Nintendo World theme. Located in the highly sought-after, guard-gated Windsor Hills community, owners and guests enjoy top-tier resort amenities including a lagoon-style pool, water park with slides, fitness center, movie theater, arcade, bar, convenience store, playgrounds, and sports courts—all just minutes from Central Florida’s world-class attractions. Selller is a licensed real estate agent.

7788 Basnett Circle, Kissimmee

Listing courtesy of LA ROSA REALTY LLC. 321-939-3748