Windsor At Westside Homes with Trail(s) Amenities

Welcome to Windsor at Westside, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This enchanting community is designed for those who appreciate the perfect blend of luxury and leisure, making it an ideal choice for families, retirees, and everyone in between.

Windsor at Westside features an impressive array of homes, each thoughtfully crafted to provide comfort and style. With a variety of floor plans ranging from cozy townhomes to spacious single-family residences, there’s a perfect fit for everyone. The homes boast modern finishes, open-concept layouts, and private outdoor spaces that invite you to relax and enjoy the Florida sunshine.

One of the standout features of Windsor at Westside is its abundant amenities. Residents can take advantage of beautifully landscaped trails that wind through the community, perfect for morning jogs, evening strolls, or leisurely bike rides. The trails connect to various recreational areas, encouraging an active lifestyle while fostering a sense of community among neighbors.

In addition to the scenic trails, the subdivision offers a resort-style clubhouse, a sparkling pool, and a state-of-the-art fitness center, ensuring that there’s always something to do. Families will appreciate the nearby parks, playgrounds, and top-rated schools that make Windsor at Westside not just a place to live, but a place to thrive.

Experience the charm and convenience of Windsor at Westside, where every day feels like a vacation and the best of Kissimmee is at your doorstep. Come and discover your dream home in this delightful community today!

Newest Windsor At Westside Homes with Trail(s) Amenities

$412,900

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code

Welcome to your slice of paradise at Windsor at Westside! Fully furnished and Airbnb-ready, this spacious 5-bedroom, 4.5-bath townhome with a private pool is located in one of Greater Orlando’s most sought-after short-term rental communities. Designed to comfortably accommodate 14+ guests, this property is ideal as both a personal getaway and an income-producing investment. The open-concept floorplan creates a bright, inviting atmosphere, enhanced by modern finishes and ample space for gathering and entertaining. Step outside to your private screened-in pool—perfect for unwinding after a day at the parks or enjoying Florida’s year-round sunshine in total privacy. The HOA delivers exceptional value, covering cable, internet, trash removal, lawn care, and 24/7 guard-gated security, offering a truly low-maintenance ownership experience. Residents and guests enjoy access to world-class resort amenities, including a 10,000 sq. ft. clubhouse, resort-style pool with lazy river and splash zone, hot tub, fitness center, arcade, sports courts, sand volleyball, playground, on-site market and deli, concierge services, and the popular Tu Casa Tiki Bar. Ideally located just minutes from Walt Disney World, with easy access to shopping, dining, and major attractions, this property offers the perfect blend of lifestyle and investment potential. Whether you’re expanding your short-term rental portfolio or searching for a vacation home that pays for itself, this opportunity checks all the boxes. Schedule your private showing today.

2015 Majorca Drive, Kissimmee

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