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 offers an ideal blend of luxury and comfort, making it the perfect destination for families, retirees, and everyone in between.

Windsor At Westside is known for its beautiful homes that boast modern designs and spacious layouts, catering to various lifestyles. Whether you’re seeking a cozy retreat or a grand family residence, you’ll find a diverse selection of properties that meet your needs. Each home is thoughtfully designed with contemporary finishes and features that enhance both aesthetics and functionality.

One of the standout features of Windsor At Westside is its impressive array of amenities, particularly the scenic trails that wind through the community. These trails invite you to immerse yourself in the natural beauty of the area, offering a perfect setting for morning jogs, leisurely strolls, or biking adventures with family and friends. The lush landscapes and serene surroundings create an atmosphere of tranquility that residents cherish.

In addition to the trails, Windsor At Westside boasts a wealth of community amenities, including a resort-style pool, a state-of-the-art fitness center, and recreational areas perfect for gatherings and events. The community is designed to foster connections among neighbors, making it easy to build lasting friendships.

Located just minutes from the excitement of Orlando’s attractions, shopping, and dining, Windsor At Westside offers the perfect balance of relaxation and entertainment. Experience the charm of this exceptional community, where your dream home awaits!

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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