Windsor Hills Homes with Pool Community Features

Windsor Hills Homes with Pool Community Features

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

Windsor Hills is particularly celebrated for its stunning homes, many of which come with private pools, offering the perfect oasis for relaxation and recreation. Imagine stepping out of your spacious, beautifully designed home and diving into your own sparkling pool, surrounded by lush landscaping and the warm Florida sunshine. Whether you’re hosting a family barbecue, enjoying a quiet evening under the stars, or simply soaking up the sun, a poolside lifestyle awaits you here.

Beyond the individual homes, Windsor Hills boasts a wealth of community features that enhance the living experience. Residents have access to a state-of-the-art clubhouse, complete with a resort-style pool, fitness center, and game room. The community also offers sports courts for tennis and basketball, as well as a playground for the little ones, ensuring that there’s something for everyone to enjoy.

With its prime location, Windsor Hills provides easy access to the world-renowned attractions of Orlando, including theme parks, shopping, and dining options, while still offering a serene retreat from the hustle and bustle.

Discover the charm and convenience of Windsor Hills, where your dream home with a pool awaits, ready to create lasting memories for you and your family. Come and experience the lifestyle that this exceptional community has to offer!

Newest Windsor Hills Homes with Pool Community Features

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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