Windsor Hills Real Estate

Welcome to Windsor Hills, a captivating subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This enchanting community is not just a place to live; it’s a lifestyle designed for those who appreciate comfort, convenience, and a touch of magic.

Windsor Hills is renowned for its stunning vacation homes and luxurious amenities, making it a perfect choice for families and investors alike. Just minutes away from the world-famous Walt Disney World Resort, residents enjoy the unique advantage of being close to the magic while also relishing the tranquility of a suburban retreat. The subdivision boasts a variety of beautifully designed homes that cater to diverse tastes and lifestyles, ensuring that everyone can find their dream residence.

The community is rich in amenities, featuring a sparkling resort-style pool, a well-equipped fitness center, and a delightful clubhouse, perfect for social gatherings and family fun. The expansive playgrounds and sports courts provide ample opportunities for outdoor activities, promoting a healthy and active lifestyle for residents of all ages.

Windsor Hills is not just about beautiful homes; it’s about building a vibrant community. With its friendly atmosphere and engaging social events, neighbors quickly become friends, creating a warm and welcoming environment. The nearby shopping centers, restaurants, and recreational areas add to the convenience, making daily life a breeze.

Experience the charm of Windsor Hills, where comfort meets convenience, and every day feels like a vacation. Come and discover your new home in this delightful Kissimmee community!

Newest Listings in Windsor Hills

$719,000

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

Welcome to this exceptional 6-bedroom, 4-bathroom vacation home located in the highly sought-after Windsor Hills Resort, one of the closest vacation rental communities to Walt Disney World! Being sold FULLY FURNISHED AND TURNKEY, this beautifully themed property offers an outstanding opportunity for buyers seeking a personal vacation retreat, second home, or short-term rental investment in the heart of Central Florida. This spacious home features six thoughtfully decorated bedrooms, including two king suites with private bathrooms and spectacular themed bedrooms. Each room has been carefully designed to create a memorable vacation experience. Entertainment is a major highlight, with an incredible Star Wars-inspired game room featuring arcade games, billiards, air hockey, foosball, and basketball. The spacious main living area offers comfortable seating, a large-screen television, and a dedicated karaoke area, making this home ideal for entertaining family and guests. Step outside to your private tropical retreat featuring a 24-by-14-foot swimming pool, relaxing spa, expansive pool deck, outdoor dining area, and lounge seating. This inviting outdoor space provides the perfect setting to relax after a day enjoying Central Florida's world-famous attractions. EXTENSIVE RECENT UPDATES AND IMPROVEMENTS! The property features a new water heater (2026), new washer (2026), new microwave (2026), sliding glass door replacement (2025), upstairs air-conditioning system replacement (2024), downstairs air-conditioning system replacement (2019), and updated upstairs flooring installed approximately 2021–2022. These improvements add to the home's comfort, functionality, and overall appeal. The fully equipped kitchen, generous living spaces, and thoughtfully designed bedroom layout provide everything needed for comfortable extended stays and larger groups. Schedule your private showing today!

2624 Bowring Street, Kissimmee

$699,900

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

Professionally redesigned and offered fully furnished, this exceptional 5-bedroom, 5-bath pool home in the sought-after Windsor Hills Resort delivers the ultimate Central Florida vacation home experience just minutes from Walt Disney World. Thoughtfully designed for both comfort and entertainment, the home features two spacious primary suites on the first floor, three additional ensuite bedrooms, and accommodations ideal for large families and vacation groups. Guests of all ages will love the dedicated home theater, immersive Harry Potter and Minions-themed bedrooms, and private screened pool and spa, creating a memorable stay long after the parks close. The open-concept living area provides the perfect gathering space, while the well-appointed kitchen and generous dining areas make hosting effortless. Located within the guard-gated Windsor Hills Resort, owners and guests enjoy access to one of Orlando's premier vacation communities featuring a resort-style lagoon pool with water slides, splash park, clubhouse, fitness center, arcade, sports courts, playgrounds, and more. With its unbeatable location, impressive entertainment spaces, and proven appeal to vacationing families, this turnkey home is equally suited as a personal retreat, second home, or short-term rental investment. For investors, this property offers an established short-term rental history with approximately $68,000 in annual bookings for both 2025 and 2026, plus a substantial number of reservations already secured for 2027. A detailed rental history and future reservation report is available for review.

7742 Comrow St, Kissimmee

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