Windsor At Westside; Windsor/Westside Homes with Trail(s) Amenities

Windsor At Westside; Windsor/Westside Homes with Trail(s) Amenities

Welcome to Windsor at Westside, a stunning community nestled in the heart of Kissimmee, Florida. Located in Osceola County, this vibrant subdivision offers an enchanting blend of luxury living and family-friendly amenities, making it the perfect place to call home.

Windsor at Westside is renowned for its charming atmosphere and beautifully designed homes, each crafted with modern aesthetics and functionality in mind. Whether you're looking for a spacious single-family home or a cozy retreat, this community has something to suit every lifestyle. With a variety of floor plans and styles, you'll find the perfect space that meets your needs.

One of the standout features of Windsor at Westside is its exceptional amenities. Residents have access to a stunning clubhouse, resort-style pool, and a state-of-the-art fitness center, ensuring that leisure and wellness are just steps away from your front door. The community also boasts picturesque walking trails, perfect for morning jogs or evening strolls with family and friends. These trails weave through the lush landscaping, offering a serene escape amidst the hustle and bustle of everyday life.

In addition to its beautiful homes and amenities, Windsor at Westside is conveniently located near major attractions, shopping, and dining options, making it an ideal location for both families and professionals. With easy access to the excitement of Orlando and the tranquility of Kissimmee, you’ll enjoy the best of both worlds.

Discover the charm and convenience of Windsor at Westside, where your dream home awaits!

Newest Windsor At Westside; Windsor/Westside Homes with Trail(s) Amenities

$445,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside; Windsor/Westside SubDv. ⋅ 34747 Zip Code
TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Upgraded laminate floor; new dryer/washer (2025); two new king bed and bunkbed Star War theme in loft; Harry Potter theme and Disney Cruise theme in tow rooms Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river plash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between Champions Gate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

8904 Sydney Avenue, Kissimmee
$449,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside; Windsor/Westside SubDv. ⋅ 34747 Zip Code
TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| END UNIT Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: End Unit Star War loft; Frozen and Nemo theme rooms Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river splash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between ChampionsGate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

8932 Sydney Avenue, Kissimmee
$445,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside; Windsor/Westside SubDv. ⋅ 34747 Zip Code
TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Newly upgraded laminate floor Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river Kids’ splash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between ChampionsGate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

8942 Sydney Avenue, Kissimmee
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