Windsor Hills Homes with Sidewalk Exterior Features

Welcome to Windsor Hills, a charming and vibrant subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. Known for its family-friendly atmosphere and stunning landscapes, Windsor Hills is the perfect place for those seeking a blend of comfort, convenience, and community spirit.

Windsor Hills boasts a delightful array of homes, each designed with modern living in mind. One of the standout features of this community is the inviting sidewalks that line the streets, encouraging residents to take leisurely strolls, enjoy evening walks, or engage in friendly conversations with neighbors. These sidewalks not only enhance the aesthetic appeal of the neighborhood but also promote an active lifestyle for families and individuals alike.

The homes in Windsor Hills are known for their spacious layouts and beautiful exteriors, often featuring well-maintained gardens and charming architectural details. Whether you’re looking for a cozy retreat or a larger family home, Windsor Hills offers a variety of options to suit every taste and budget.

Residents enjoy easy access to a wealth of nearby amenities, including shopping centers, dining options, and recreational facilities, ensuring that everything you need is just a stone's throw away. Plus, with the magic of Walt Disney World and other attractions only a short drive away, Windsor Hills is not just a place to live; it's a lifestyle filled with adventure and excitement.

Experience the warmth and charm of Windsor Hills—where community meets comfort in the heart of Kissimmee!

Newest Windsor Hills Homes with Sidewalk Exterior Features

$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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