Windsor Hills Homes with Sidewalk Exterior Features

Windsor Hills Homes with Sidewalk Exterior Features

Welcome to Windsor Hills, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community is renowned for its family-friendly atmosphere, making it an ideal destination for both homeowners and investors alike.

Windsor Hills boasts an array of beautifully designed homes, each featuring inviting sidewalk exterior designs that encourage strolls through the neighborhood. Imagine leisurely walks along tree-lined streets, where neighbors greet each other with warm smiles and children play freely in the safe, open spaces. The sidewalks not only enhance the aesthetic appeal of the community but also promote an active lifestyle, encouraging residents to enjoy the Florida sunshine and fresh air.

The homes in Windsor Hills are a perfect blend of modern comfort and classic charm, offering spacious layouts and contemporary finishes that cater to a variety of tastes. Whether you’re searching for a cozy retreat or a larger family residence, you’ll find options that suit your needs. Many homes also feature private backyards, perfect for hosting barbecues or enjoying peaceful evenings under the stars.

Windsor Hills is ideally located just minutes away from the excitement of Orlando's theme parks, shopping centers, and dining options, making it a prime location for those who appreciate both tranquility and adventure. With its welcoming community spirit and exceptional amenities, Windsor Hills is not just a place to live; it’s a place to thrive. Come and discover your dream home in this enchanting neighborhood today!

Newest Windsor Hills Homes with Sidewalk Exterior 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

Start Your Search

How much is your home worth?

Get instant property value now!