Windsor Hills Homes with Community Pool type

Windsor Hills Homes with Community Pool type

Welcome to Windsor Hills, a stunning gated community nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This picturesque subdivision is renowned for its family-friendly atmosphere and exceptional amenities, making it a perfect choice for both vacationers and residents alike.

Windsor Hills boasts a diverse selection of beautifully designed homes, from spacious townhouses to luxurious single-family residences, ensuring there’s something for everyone. Each home is thoughtfully crafted to provide comfort and style, featuring modern finishes, open floor plans, and private outdoor spaces ideal for enjoying the sunny Florida weather.

One of the standout features of Windsor Hills is its fantastic community pool, where residents can unwind and socialize under the warm sun. The pool area is complemented by a splash pad for the little ones, making it a safe and fun environment for families. Whether you’re lounging poolside with a good book or hosting a barbecue with friends, the community pool serves as a central hub for relaxation and recreation.

Beyond the pool, Windsor Hills offers a wealth of amenities, including a clubhouse, fitness center, sports courts, and walking trails, ensuring that residents can maintain an active lifestyle while enjoying the beautiful surroundings. With its prime location just minutes from the world-renowned attractions of Walt Disney World, Universal Studios, and a variety of dining and shopping options, Windsor Hills is not just a place to live; it’s a lifestyle.

Come explore the charm of Windsor Hills and discover your dream home in this enchanting community today!

Newest Windsor Hills Homes with Community Pool type

2788 Almaton Loop Unit 102, Kissimmee
$270,000
2 Beds ⋅ 2 Baths ⋅ Windsor Hills SubDv. ⋅ 34747 Zip Code
YOUR DISNEY GETAWAY—FULLY FURNISHED, TURNKEY, AND READY FOR FUN! Just 2.5 miles from the Disney entrance, this 2-bedroom, 2-bath GROUND-FLOOR condo in Windsor Hills Resort is your opportunity to own a vacation escape with SHORT-TERM RENTAL potential. Make it your personal retreat, welcome vacation guests, or enjoy a little of both. Just bring your suitcase and let the memories begin! No stairs to climb with luggage, groceries, or tired little ones! Inside, the open living and dining areas provide a comfortable place to gather, share meals, and unwind after a day at the parks. The kitchen offers ample cabinetry and a breakfast bar for easy mornings before heading out. Two bedrooms and two full bathrooms provide room to recharge, while an in-unit laundry room adds everyday convenience. Step through the sliding glass doors onto your SCREENED LANAI overlooking a grassy area—a relaxing spot for morning coffee or a quiet evening planning tomorrow’s adventures. At Windsor Hills, staying “home” can be just as much fun as going out! This 24-hour guard-gated resort features a sprawling beach-entry-style pool, waterpark, waterslide, and splash pad. The clubhouse includes a fitness center, theatre, game rooms, welcome center, and Sundry Shop. Outdoor tennis courts, a basketball court, and a picnic/grill area are all adjacent to this condo building, putting even more recreation close at hand. Association fees include water, high-speed Internet, cable TV, trash service, and 24-hour resort security. With Disney just 2.5 miles away and dining, shopping, and entertainment nearby, you’re perfectly positioned for everything a Central Florida vacation should be. FULLY FURNISHED. TURNKEY. GROUND FLOOR. Why just book the vacation when you could own the getaway?

2788 Almaton Loop Unit 102, Kissimmee
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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