Windsor At Westside; Windsor/Westside Real Estate

Windsor At Westside; Windsor/Westside Real Estate

Welcome to Windsor at Westside, a stunning subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This enchanting community embodies the perfect blend of luxury, comfort, and convenience, making it an ideal choice for families, vacationers, and investors alike.

Windsor at Westside is renowned for its beautifully designed homes, ranging from spacious townhouses to elegant single-family residences. Each property showcases modern architecture and high-quality finishes, ensuring that every homeowner enjoys a touch of sophistication. With floor plans that cater to diverse lifestyles, you’ll find the perfect space whether you’re seeking a cozy retreat or a grand family abode.

One of the standout features of Windsor at Westside is its resort-style amenities. Residents can indulge in a lavish clubhouse, a sparkling swimming pool, and a well-equipped fitness center. The community also boasts a lazy river, sports courts, and playgrounds, providing endless opportunities for recreation and relaxation. Surrounded by lush landscaping and serene water views, Windsor at Westside is a true oasis.

Location is key, and Windsor at Westside is conveniently situated just minutes away from the world-famous attractions of Orlando, including Walt Disney World, Universal Studios, and SeaWorld. With easy access to major highways, shopping centers, and dining options, you'll find everything you need right at your doorstep.

Whether you’re looking for a vacation home, a permanent residence, or an investment opportunity, Windsor at Westside offers a lifestyle that’s hard to resist. Come and experience the charm of Kissimmee and discover your dream home in this exquisite community today!

Newest Listings in Windsor At Westside; Windsor/Westside

$445,000
5 Beds ⋅ 5 Baths ⋅ O6413060 MLS ⋅ 2428 BLDG.
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 ⋅ O6412966 MLS ⋅ 2428 BLDG.
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 ⋅ O6404821 MLS ⋅ 2428 BLDG.
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
Start Your Search