Windsor At Westside Homes with Trail(s) Amenities

Welcome to Windsor at Westside, a captivating subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This stunning community is designed for those seeking a perfect blend of comfort, luxury, and convenience, making it an ideal place to call home.

Windsor at Westside features an impressive collection of single-family homes, each thoughtfully crafted to suit a variety of lifestyles. With spacious floor plans, modern finishes, and an array of customizable options, you’ll find the perfect sanctuary for you and your family. The homes are surrounded by lush landscapes and serene views, creating a tranquil atmosphere that invites relaxation and enjoyment.

One of the standout features of Windsor at Westside is its exceptional amenities. Residents can take advantage of the community's beautiful trails, perfect for morning jogs, evening strolls, or leisurely bike rides. The well-maintained paths wind through the scenic surroundings, providing a peaceful escape from the hustle and bustle of everyday life.

In addition to the trails, Windsor at Westside boasts a magnificent clubhouse, a resort-style pool, and a state-of-the-art fitness center, ensuring there's always something to do and enjoy. The community is also conveniently located near shopping, dining, and entertainment options, making it easy to access everything you need.

Whether you’re looking for a primary residence, a vacation home, or a rental investment, Windsor at Westside offers a lifestyle of comfort and convenience in one of Florida's most desirable locations. Come experience the charm of this vibrant community and discover your dream home today!

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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