Windsor Hills Real Estate - Search all Windsor Hills homes and townhouses for sale.

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 6 SubDv. ⋅ 34747 Zip Code

Busy rental: Next available to view is July 26! Minutes to Animal Kingdom! Guest friendly, fun, and full of upgrades! This vacation home has been thoughtfully improved with themed spaces throughout, including a fully themed garage/game area guests will love. Located right next to one of the playgrounds, it offers extra convenience for families and a standout experience in the highly desirable Windsor Hills community.

2623 Pawnall Street, Kissimmee

$699,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

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

$695,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 5 SubDv. ⋅ 34747 Zip Code

Beautifully professionally decorated and totally renovated, this exceptional vacation home is truly turnkey and designed to impress both owners and guests alike. The spacious interior has luxury vinyl plank flooring throughout the first floor, upstairs hallway, and primary bath, creating a stylish and durable modern look. The home is packed with entertainment and fun, including an exciting game room with basketball, air hockey, and arcade game that guests of all ages will love. The themed bedrooms bring the magic to life with incredible Mickey Mouse and Harry Potter-inspired designs, making this property highly desirable as a short-term rental or family retreat. Located in the highly sought-after Windsor Hills Resort, one of the closest resort communities to Walt Disney World, owners and guests enjoy world-class amenities including a huge lagoon-style pool, water park with slides and splash pad, clubhouse with fitness center and movie theater, sundry deli, tennis courts, and playgrounds. Whether you are looking for a vacation getaway, investment property, or income-producing short-term rental, this stunning home checks every box.

7805 Beechfield Street, Kissimmee

$649,000

5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

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

$630,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

Welcome to this beautifully maintained 6-bedroom, 4-bathroom fully furnished home located in the highly sought-after Windsor Hills Resort in Kissimmee. Designed for comfort and convenience, this spacious property is ideal as a primary residence, vacation retreat, or income-producing short-term rental. Step inside to an open and inviting floor plan featuring generous living spaces perfect for gatherings. The home comes turn-key furnished, allowing for a seamless move-in or immediate rental potential. Guests of all ages will enjoy the dedicated game room, offering endless entertainment. Outdoors, unwind in your private screened pool, an ideal spot to relax after a day at the parks or soak up Florida sunshine in complete privacy. With six well-appointed bedrooms and four full bathrooms, there’s ample space for family and guests alike. Situated just minutes from world-class attractions, shopping, dining, and entertainment, Windsor Hills also offers resort-style amenities including a clubhouse, water park, fitness center, and more—all within a secure, gated community. This exceptional home truly offers the best of Florida resort living. Schedule your private showing today.

7759 Tosteth Street, Kissimmee

$625,000

5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

Welcome to this beautifully updated beach-themed oasis, a fully renovated and furnished STR home located in the heart of Kissimmee. This property underwent a complete renovation in 2022, featuring a modernized kitchen with updated cabinetry, countertops, and appliances, along with new flooring and fresh interior paint throughout. Major capital improvements include a new roof (2022) and a recently resurfaced private pool (2025), offering peace of mind and long-term value. Designed for both comfort and functionality, each bedroom features its own dedicated full bathroom, providing privacy and convenience for guests—an setup for STR and multi-family use. The home also includes a converted garage game room equipped with ping pong, foosball, and arcade games, creating a fun and engaging entertainment space that enhances guest experience and rental appeal. The open-concept layout flows seamlessly to a screened-in lanai and private pool area, delivering the indoor-outdoor living experience for entertaining or relaxing after a day at nearby attractions. Located just minutes from Walt Disney World, shopping, dining, and major highways, this home is perfectly positioned for both strong STR income potential and long-term appreciation. The HOA provides exceptional value, including lawn service, irrigation maintenance, daily valet trash pickup, internet, basic cable, and a 24/7 manned guard gate for added security and convenience. Residents and guests enjoy access to a resort-style amenity package, including a large clubhouse, tropical community pool with water park slide and zero-entry access, open-air lounge, convenience store, fitness center, movie theater, billiards/game room, table tennis, lighted basketball and tennis courts, sand volleyball court, putting green, RV/boat parking area, and multiple playgrounds.

2648 Dinville Street, Kissimmee

$615,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills SubDv. ⋅ 34747 Zip Code

Welcome to your dream Florida oasis at 2648 DAULBY ST, nestled in the highly sought-after, guard-gated Windsor Hills Resort. This fully furnished 6-bedroom, 3.5-bathroom home offers the ultimate turnkey opportunity, making it a perfect fit as a high-yield investment property, an unforgettable vacation home, or a spacious primary residence. Move-in ready and meticulously updated, the property features a new roof, new flooring, a new water heater, and stunning new countertops throughout. Step out back to your private, screened-in oasis with a pristine pool and spa, or head inside to the converted garage-turned-game room for endless indoor entertainment. Beyond the front door, owners and guests have access to Windsor Hills’ world-class, five-star amenities, including a massive double-waterslide water park, a zero-entry lagoon pool, a 10,000 sq. ft. clubhouse with an HD movie theater, a state-of-the-art fitness center, a marketplace/grill, and lighted tennis, basketball, and sand volleyball courts. Location is everything, and this property delivers, sitting just minutes from Walt Disney World and Central Florida’s premier dining, shopping, and major entertainment attractions. Whether you are looking to maximize short-term rental revenue or enjoy the resort lifestyle every day, this exceptional property is an opportunity you don’t want to miss.

2648 Daulby Street, Kissimmee

$615,000

4 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 1 SubDv. ⋅ 34747 Zip Code

Welcome to this exceptional turnkey vacation rental opportunity in the highly sought-after Windsor Hills Resort! This fully furnished 4 bedroom, 4 bath home is designed to entertain guests of all ages with custom themed bedrooms, a game room, private screened pool and spa, and an inviting open-concept floor plan perfect for any gatherings. The spacious kitchen and a large breakfast bar overlook the main living area. Guests will love the professionally themed Disney-inspired bedrooms, while the converted garage game room provides endless entertainment. Located just 5 minutes from Disney and minutes from Universal Studios, SeaWorld, Legoland, Shopping, Dining, and more, this property offers both an incredible vacation experience and strong income-producing potential. Windsor Hills Resort features many amenities including a clubhouse, fitness center, movie theater, arcade, resort-style pool with waterslides, sports courts, playgrounds, and gated security. Whether you're looking for a personal retreat, investment property, or both, this home is ready to impress. Schedule your private showing today!

7743 Comrow Street, Kissimmee

$610,000

5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

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

$599,900

4 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 6 SubDv. ⋅ 34747 Zip Code

Welcome to 7755 Grassendale Street! This TURNKEY, well-maintained 4-bedroom, 4-bath home is move-in ready and ideal as a primary residence or short-term vacation rental. The open-concept layout features a large foyer, spacious dining area, family room, and a well-appointed kitchen with stainless steel appliances, granite countertops, breakfast bar, and nook. All bedrooms feature luxury vinyl plank flooring and are tastefully themed, while the main living areas are tile. The converted 2-car garage (2021) is air-conditioned and serves as an entertainment space with a home theater, gaming consoles, and a sit-down arcade game. Step outside to the covered lanai and enjoy the refurbished (2022) pool and spa—perfect for relaxing in the Florida sun. The community offers a 24-hour guard-gated entrance and resort-style amenities, including a 10,000 sq. ft. clubhouse, lagoon-style pool with water slides, fitness center, movie theater, sports courts, playground, and walking trail. Conveniently located minutes from Disney, with dining, shopping, and everyday essentials nearby. This truly is a MUST SEE home!

7755 Grassendale Street, Kissimmee

Windsor Hills Homes for Sale

Windsor Hills Homes For Sale