Windsor At Westside Homes with Trail(s) Amenities

Welcome to Windsor at Westside, a captivating community nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This beautifully designed subdivision offers a perfect blend of modern living and natural beauty, making it an ideal choice for families, retirees, and anyone looking for a serene lifestyle.

Windsor at Westside is renowned for its stunning homes, which are thoughtfully crafted with a range of floor plans to suit various lifestyles and preferences. Each residence boasts spacious interiors, contemporary finishes, and ample outdoor space, perfect for entertaining or simply enjoying the Florida sunshine.

One of the standout features of this community is its extensive trail system. Residents have access to well-maintained walking and biking trails that wind through lush landscapes, providing opportunities for outdoor recreation and relaxation. Whether you're taking a leisurely stroll with family or enjoying a brisk morning jog, the trails offer a scenic backdrop that enhances your daily routine.

In addition to the trails, Windsor at Westside also offers a host of amenities designed to enrich the living experience. From resort-style pools and fitness centers to playgrounds and gathering spaces, there’s something for everyone to enjoy. The community's vibrant atmosphere fosters connections among neighbors, making it easy to form lasting friendships.

Located just minutes from the excitement of Orlando’s theme parks, shopping, and dining, Windsor at Westside is the perfect place to call home. Experience the charm of this exceptional community and discover why so many choose to make it their own. Embrace the lifestyle you’ve always dreamed of in Windsor at Westside!

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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