Windsor At Westside Homes with Trail(s) Amenities

Welcome to Windsor at Westside, a stunning subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This vibrant community offers an idyllic blend of modern living and natural beauty, making it a perfect haven for families, retirees, and everyone in between.

Windsor at Westside boasts an impressive selection of homes designed with elegance and comfort in mind. From spacious single-family residences to charming townhomes, each property features contemporary finishes and thoughtful layouts that cater to a variety of lifestyles. With multiple floor plans available, you’re sure to find the perfect space to call home.

One of the standout features of Windsor at Westside is its commitment to outdoor living. The community is enveloped by lush landscapes and serene walking trails, providing residents with ample opportunities to enjoy Florida's beautiful weather. Whether you prefer a leisurely stroll or an invigorating jog, the winding trails throughout the subdivision are perfect for staying active while soaking in the natural surroundings.

In addition to the scenic trails, Windsor at Westside offers a wealth of amenities designed to enhance your lifestyle. Residents can take advantage of the sparkling resort-style pool, a state-of-the-art fitness center, and a clubhouse perfect for social gatherings. Children can enjoy the playground, while families can host barbecues in the designated picnic areas.

With its prime location, exceptional amenities, and charming homes, Windsor at Westside is not just a neighborhood; it’s a community where memories are made and cherished. Come discover the lifestyle that awaits you in this wonderful Kissimmee enclave!

Newest Windsor At Westside Homes with Trail(s) Amenities

$405,000

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

Welcome to 8900 Sydney Ave in Windsor at Westside, a beautifully positioned end unit 5 bedroom, 4.5 bath townhome offering 2,263 square feet in one of the most sought after vacation home communities near Disney. Originally purchased as the builder’s model, this home stands out from the typical inventory with a brighter, more elevated feel, a desirable end unit location, and interior finishes and furnishings that show far better than many competing townhomes in the community. The cream kitchen, stylish window treatments, upgraded bedroom theming, and strong overall presentation give this property the kind of visual appeal buyers and guests notice right away. Whether you are looking for a personal getaway, a second home, or an income producing vacation property, this townhome offers the combination of location, layout, and resort appeal that today’s buyers want. Windsor at Westside is a gated resort community with a large clubhouse, resort style pool, lazy river, waterslide, fitness center, tiki bar, arcade, and convenient access to the Disney parks, dining, and shopping. With its private pool, popular 5 bedroom layout, and premium end unit positioning, 8900 Sydney Ave is a standout opportunity in a community known for strong guest appeal and resort style living.

8900 Sydney Avenue, Kissimmee

$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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