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)
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
Residential
KISSIMMEE, Florida 34747
6Bedroom(s)
4Bathroom(s)
70Picture(s)
3,142Sqft
Located in the exclusive gated community of Windsor at Westside, this beautiful two-story residence, sold fully furnished, is the perfect combination of comfort, sophistication, and excellent investment potential.
With 6 bedrooms, 4 full bathrooms, and 1 powder room, the house features a modern open-concept layout, providing spacious, integrated, and well-lit environments.
$550,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
87Picture(s)
2,263Sqft
Step into this beautifully furnished 5-bedroom, 4.5-bathroom townhome at Windsor at Westside, one of Kissimmee's popular vacation communities. With 2,263 square feet of living space over two floors, the property offers a spacious layout designed with vacation guests and comfortable family living in mind.
$390,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
56Picture(s)
4,041Sqft
PRICE ADJUSTMENT!!
Beautifully decorated and Spacious 8-bedroom, 6-bathroom vacation home just minutes from Disney and major attractions. Ideal for short-term rental, investment, or personal use. This well-maintained, fully furnished corner lot property features an open floor plan, fully equipped kitchen, large living and dining areas, and generously sized bedrooms with excellent decoration.
$649,900
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
20Picture(s)
4,041Sqft
Turnkey 8-bedroom, 6-bath fully furnished pool home located in the highly desirable Windsor at Westside Resort. This well-maintained property offers over 4,000 sq ft of living space with a functional and spacious layout ideal for short-term rental use. The home features an open-concept main floor with a large kitchen, breakfast bar, formal dining area, and expansive living room.
$644,900
Residential
KISSIMMEE, Florida 34747
9Bedroom(s)
6Bathroom(s)
51Picture(s)
4,391Sqft
Welcome to this spacious 9-bedroom, 6-bath pool home located in the sought-after Windsor at Westside Resort community of Kissimmee! Offering approximately 4,391 square feet of living space, this impressive two-story home has been recently refreshed with new carpeting and fresh interior and exterior paint, making it ready for its next owner.
$639,900
Residential
KISSIMMEE, Florida 34747
9Bedroom(s)
6Bathroom(s)
37Picture(s)
4,391Sqft
Experience the ultimate blend of luxury, comfort, and investment potential in this stunning fully furnished 9-bedroom, 6-bathroom lakefront home. Turnkey and short-term rental approved, this exceptional property is the perfect opportunity for investors seeking a high-performing vacation rental or homebuyers looking for an unforgettable Florida retreat.
$678,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
48Picture(s)
2,263Sqft
Turnkey 5-Bedroom Townhome – Short-Term Rental Approved!
Welcome to this beautifully furnished 5-bedroom, 4.5-bathroom townhome, thoughtfully designed with fun Mickey Mouse and Harry Potter-themed bedroom, perfect for vacationers and investors alike.
This move-in-ready property comfortably accommodates up to 12 guests and offers the ideal combination of space, comfort, and entertainment.
$430,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
79Picture(s)
4,041Sqft
Imagine pulling into a community where every day feels like you're on vacation. Located in the 24/7 guard-gated community of Windsor at Westside, this sprawling 8-bedroom, 6-bathroom home spans over 4,000 square feet of space designed for bringing loved ones together. Best of all, it comes fully furnished and turnkey, making it completely move-in or rental-ready from day one.
$655,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
50Picture(s)
4,041Sqft
Discover this stunning 8-bedroom, 6-bathroom luxury home located in the highly sought-after Windsor at Westside Resort, just 15 minutes from Walt Disney World! This property sits on one of the most desirable lots in the community —just a one-minute walk to the magnificent clubhouse in Phase I. This turn-key, fully furnished vacation home is ready for short-term rental or personal use.
$695,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
58Picture(s)
2,263Sqft
Welcome to this beautifully maintained 5-bedroom, 4.5-bathroom home located in the highly sought-after Windsor at Westside Resort in Kissimmee. Whether you're searching for a primary residence, vacation home, or investment property, this home offers the perfect blend of comfort, style, and convenience.
$495,000
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).