Windsor Hills, FL homes for sale & real estate

Windsor Hills, FL Homes for Sale

Own this spacious, 5 Bedroom, 5 Bath home located inside of the 5-STAR Windsor Hills Resort in Kissimmee, Florida. The Windsor Hills Resort is in demand as a premier destination — it is the closest vacation style resort and vacation rental community to Disneyworld! Move into this fully-furnished, luxury villa, or join the successful Airbnb community and generate vacation rental income from your turnkey investment. This completely furnished and professionally decorated home is move-in ready and features a screened lanai with heated, gentle saltwater pool with spa. At entry level, the home has an open-floor plan, offering two dining areas plus kitchen counter seating and a large adjoini

Windsor Hills, FL Homes for Sale

Peace of mind and lasting value with a brand-new shingle roof being installed October 2025! Discover this exceptional 7-bedroom, 4-bathroom fully furnished home in the highly sought-after Windsor Hills Resort, just 4 miles from Walt Disney World! This property offers a rare advantage—no rear neighbor and a spacious open view of lush green space and trees, creating a serene and private setting. Perfect as a vacation retreat or short-term rental investment, this spacious home boasts a versatile floor plan designed for entertaining and creating unforgettable memories. Unlike most homes in Windsor Hills, this floor plan is unique: originally a 6-bedroom layout, the front living room has b

Windsor Hills, FL Homes for Sale

Stunning 6-Bedroom Home Just 5 Minutes from Walt Disney World! Welcome to this beautiful and spacious residence located in the highly sought-after Windsor Hills Resort, a premier 24-hour guard-gated community just minutes from the magic of Walt Disney World. Whether you're seeking a dream vacation home, a high-performing short-term rental investment, or a full-time residence in Central Florida, this property offers outstanding value and an unbeatable location. This well-maintained six-bedroom, four-bathroom home also features a versatile bonus room that can be used as an office or extra bedroom. The home’s open-concept living and dining areas flow seamlessly into a fully equipped kitc

Windsor Hills, FL Homes for Sale

Price Reduction! Book your Appointment now! Welcome to this well maintained pool home, perfectly situated on one of the most private streets in the highly desirable Windsor Hills Community. With a strong history as a short-term rental and future bookings already in place, this property is both a charming retreat and a smart investment. Step inside and you’ll find a warm, inviting space with five spacious bedrooms and five full bathrooms. The open-concept design allows the home to flow seamlessly from room to room, making it perfect for gathering with family and friends. Two master suites are conveniently located on the main level, while the remaining bedrooms each feature their own pr