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 vibrant Osceola County. This enchanting community is a perfect blend of luxury, comfort, and convenience, making it an ideal place for families, retirees, and everyone in between.

Windsor At Westside boasts a collection of beautifully designed homes that cater to a variety of lifestyles. From spacious single-family residences to modern townhomes, each property is crafted with meticulous attention to detail, featuring open floor plans, gourmet kitchens, and private outdoor spaces perfect for entertaining or unwinding after a long day.

One of the standout features of Windsor At Westside is its fantastic amenities, particularly the extensive trail system that winds through the community. These scenic trails invite residents to explore the natural beauty of the area, whether you enjoy a leisurely stroll, an invigorating jog, or a peaceful bike ride. The lush landscaping and serene surroundings create a tranquil atmosphere that enhances the overall living experience.

In addition to the trails, residents can take advantage of a wealth of community amenities, including a resort-style pool, fitness center, and clubhouse, fostering a sense of community and connection. Families will appreciate the nearby schools, shopping centers, and recreational opportunities that Kissimmee has to offer, ensuring that everything you need is just a stone's throw away.

Discover the charm of Windsor At Westside, where your dream home awaits amidst beautiful trails and a welcoming community. Embrace the lifestyle you've always wanted in this idyllic Florida haven!

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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