Windsor Hills Homes for Sale

Windsor Hills Homes for Sale

Welcome to Windsor Hills, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This vibrant community is known for its family-friendly atmosphere, luxurious amenities, and proximity to some of Florida's most popular attractions, making it an ideal place to call home or invest in a vacation property.

Windsor Hills boasts a wide array of stunning homes for sale, ranging from spacious townhomes to elegant single-family residences. Each property is thoughtfully designed, featuring modern kitchens, open floor plans, and private outdoor spaces perfect for enjoying the warm Florida sunshine. Whether you’re seeking a cozy retreat or a larger family home, Windsor Hills offers something for everyone.

One of the standout features of this subdivision is its resort-style amenities. Residents can take advantage of the sparkling community pool, well-equipped fitness center, and a fun-filled playground, ensuring there’s never a dull moment. The community also offers tennis courts and a clubhouse, perfect for social gatherings or simply unwinding after a long day.

Location is key, and Windsor Hills does not disappoint. Situated just minutes from the world-renowned Walt Disney World Resort and other major attractions, this community provides easy access to endless entertainment options. With nearby shopping, dining, and recreational activities, Windsor Hills is not just a place to live; it’s a lifestyle.

Explore the homes for sale in Windsor Hills today and discover the perfect blend of comfort, convenience, and charm in this thriving Kissimmee community!

Newest Windsor Hills Homes for Sale

2624 Bowring Street, Kissimmee
$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
7742 Comrow St, 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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