Windsor at Westside Homes for Sale
Real Estate Listing in the Disney Area “Super Community”
Browse Homes for Sale in Windsor at Westside
View our hand picked listings available in the Windsor at Westside resort, just minutes from Walt Disney World!
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
74Picture(s)
4,041Sqft
Buyer shall assume the existing solar contract at closing! Beautifully and tastefully decorated, this exceptional 8-bedroom, 6-bath single-family pool home is located within the highly sought-after Windsor at Westside Resort, one of the premier resort communities in the Orlando/Kissimmee area. Enjoy convenient access to world-class theme parks, dining, shopping, and entertainment.
$570,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
69Picture(s)
4,041Sqft
Buyer shall assume the existing solar contract at closing. Beautifully and tastefully decorated, this exceptional 8-bedroom, 6-bath single-family pool home is located within the highly sought-after Windsor at Westside Resort, one of the premier resort communities in the Orlando/Kissimmee area. Enjoy convenient access to world-class theme parks, dining, shopping, and entertainment.
$570,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
76Picture(s)
2,263Sqft
Experience elevated Florida living in this beautiful 5-bedroom, 5-bathroom townhome in the sought-after Windsor at Westside community. Featuring a spacious, contemporary layout designed for comfort and effortless entertaining, this exceptional residence offers the perfect blend of style, privacy and resort-inspired living.
$416,000
Residential
KISSIMMEE, Florida 34747
7Bedroom(s)
5Bathroom(s)
93Picture(s)
3,314Sqft
Short Sale. Welcome to Windsor at Westside — Guard-Gated Resort Living at its Finest! This fully furnished, turn-key 7-bedroom, 5.5-bathroom home offers 3,314 sq ft of beautifully appointed living space, perfect for short-term rental income or a luxury vacation retreat.
$500,000
Residential
KISSIMMEE, Florida 34747
6Bedroom(s)
4Bathroom(s)
38Picture(s)
3,142Sqft
Welcome to 1732 Lima Ave, an exceptional opportunity to own in one of Kissimmee’s most desirable resort communities. Located in Windsor at Westside, this beautifully designed home offers the perfect blend of luxury, comfort, and unbeatable proximity — just a few minutes from Orlando’s world-famous theme parks. Spacious layout ideal for families and vacation renters.
$525,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
100Picture(s)
4,041Sqft
Private Wooded Lot | 8 Bedrooms | 6 Bathrooms | Heated Pool & Spa | 12-Seat Movie Theater | Game Room | Fully Furnished
Discover the perfect blend of privacy, luxury, and resort-style entertainment in this beautifully furnished 8-bedroom, 6-bathroom vacation home in the sought-after Windsor at Westside community.
$699,000
Residential
KISSIMMEE, Florida 34747
9Bedroom(s)
6Bathroom(s)
53Picture(s)
4,391Sqft
2025 Gross: $133,345! First available to view Monday Sept 28! Contact your agent today!!! This is the vacation home guests remember! Updates focusing on guests enjoyment, including Star Wars, Harry Potter and Frozen themed spaces, plus a private pool, all ready for unforgettable Disney vacations.
$650,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
52Picture(s)
2,492Sqft
Welcome to this beautifully furnished 5-bedroom, 4-bathroom pool home in the sought-after Windsor at Westside Resort! SHORT-TERM RENTAL ALLOWED........ Situated on a desirable corner lot, this spacious two-story property offers an open-concept layout designed for comfortable living, entertaining, and relaxing.
$499,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
46Picture(s)
2,263Sqft
Exceptional Investment Opportunity in Windsor at Westside!
Welcome to 8859 Geneve Court, a spacious 5-bedroom, 4.5-bathroom townhome with a private pool, located in the highly desirable Windsor at Westside resort community in Kissimmee.
$388,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
27Picture(s)
2,265Sqft
Welcome to this beautiful home located at the unique Windsor At Westside. This 5 bedrooms, 4 full bathrooms and 1 half bathroom features an open plan family room, kitchen and dining area with sliding patio doors in the first floor and also one bedroom.
$479,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
89Picture(s)
4,034Sqft
Welcome to this stunning 8-bedroom, 6-bathroom vacation home in the highly sought-after Windsor at Westside gated resort community just 2.5 miles from Walt Disney World. This home is perfectly positioned for short-term rental income or a spacious primary residence in the heart of Central Florida's tourist corridor.
$699,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
65Picture(s)
4,041Sqft
Enjoy breathtaking pond views and exceptional backyard privacy in this stunning 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside community. This fully furnished residence offers the perfect blend of luxury, comfort, and investment potential, ideal as a vacation retreat or a high-performing short-term rental.
$689,000
The Best Windsor at Westside Homes for Sale
Find your perfect resort style vacation home or zoned short term rental at Windsor at Westside. Explore a collection of grand home designs ranging from 4-9 bedrooms, and 3.5-6 bathrooms with lofts. Enjoy proximity to world-class attractions, the famous Florida sunshine, and abundant shopping and dining.
This is it – the vacation rental home resort you have been waiting for, all just a few minutes from Disney. We work hard to source and then secure the very best pricing possible – the best deals are limited in supply, so be sure to call or email today to receive information on these exceptionally priced homes.
How far is Windsor at Westside to Disney World?
Windsor at Westside Resort is located just 7 miles by road from the Disney World Resort. Take Highway 192 east to 429 north to enter the park.
How far is Windsor at Westside to Universal Studios Orlando?
Go from Windsor at Westside Resort to Universal Studios in just 30 minutes. The distance between the two is 21 miles. Take 192 East to Interstate 4 northbound.
Does Windsor at Westside have a shuttle service?
Windsor at Westside does not have a shuttle service per se, however it’s conveniently located to all parts of Greater Orlando and has ample rental car options, especially from MCO airport.
How far is Windsor at Westside from Orlando International Airport (MCO)?
Windsor at Westside is a 27 mile trek from Orlando International Airport (MCO).