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 beautiful Osceola County. This vibrant community offers a perfect blend of luxury, comfort, and convenience, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle close to the excitement of Orlando.

Windsor at Westside is renowned for its exquisite homes, designed with modern living in mind. Each residence features spacious layouts, contemporary finishes, and private outdoor spaces, perfect for enjoying Florida's year-round sunshine. Whether you’re looking for a cozy family retreat or an investment property, you’ll find a variety of options to suit your needs.

One of the standout features of Windsor at Westside is its exceptional amenities, particularly the extensive network of trails that wind throughout the community. These scenic pathways invite residents to explore the natural beauty of the area, perfect for morning jogs, leisurely strolls, or biking with family and friends. The trails seamlessly connect to lush green spaces and parks, encouraging an active and healthy lifestyle.

Additionally, residents of Windsor at Westside enjoy access to a fantastic clubhouse, resort-style pool, fitness center, and sports courts, creating a wonderful sense of community and opportunities for social engagement. With its prime location just minutes from world-class attractions, shopping, and dining, Windsor at Westside is not just a place to live; it’s a place to thrive. Discover your dream home in this enchanting subdivision and embrace the vibrant lifestyle that awaits you!

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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