Windsor Hills Homes with Pool Community Features

Welcome to Windsor Hills, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida, within the scenic Osceola County. This charming community is not just a place to live; it’s a lifestyle waiting to be embraced. With its prime location, Windsor Hills offers easy access to the magical attractions of Central Florida, including the world-renowned Walt Disney World, Universal Studios, and a plethora of shopping and dining options.

Windsor Hills is renowned for its stunning homes, many of which come with private pools, creating the perfect oasis for relaxation and entertainment. Imagine stepping out of your beautifully appointed home into your own backyard paradise, where you can soak up the sun or host family barbecues by the poolside. The community features an array of amenities designed to enhance your living experience, including a resort-style clubhouse, a sparkling community pool, tennis courts, and a fitness center.

Families will appreciate the well-maintained parks and playgrounds, providing a safe and fun environment for children to play and explore. Whether you are seeking a vacation home or a permanent residence, Windsor Hills offers a warm, welcoming atmosphere that fosters a strong sense of community.

With its combination of luxurious homes, fantastic amenities, and proximity to Florida’s most popular attractions, Windsor Hills is the perfect place to call home. Discover the magic of living in this exceptional community, where every day feels like a vacation. Come and experience the charm of Windsor Hills today!

Newest Windsor Hills Homes with Pool Community Features

$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

$729,000

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

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