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
5Bedroom(s)
4Bathroom(s)
43Picture(s)
2,102Sqft
This beautifully maintained home is currently part of a successful short-term rental program, making it an excellent opportunity for both investors and end users. Thoughtfully designed and well cared for, the property offers comfort, functionality, and flexibility.
Showings are welcome with 24 hours’ prior notice, allowing for a smooth and respectful viewing experience.
$455,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
56Picture(s)
4,041Sqft
OVER $200K IN CUSTOM RENOVATIONS & THEMED UPGRADES! Welcome to the ultimate turn-key investment property at 1885 Gobi Drive in the premier, guard-gated community of Windsor at Westside. Spanning over 4,000 sq ft, this 8-Bed, 6-Bath luxury pool/spa home has been fully transformed into an elite short-term rental paying tribute to Universal’s new Epic Universe.
$629,999
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
22Picture(s)
2,492Sqft
Welcome to tastefully designed 5/bed 4/bath home with private pool facing conservation area in the prestige Community Windsor at Westside, zoned for short term vacation rental. The open floor plan seamlessly connects the living, dining, and kitchen areas, perfect for everyday living and entertaining.
$445,000
Residential
KISSIMMEE, Florida 34747
9Bedroom(s)
6Bathroom(s)
55Picture(s)
4,391Sqft
Beautiful 9-bedroom,6-bathroom water-front pool home in the highly sought-after Windsor at Westside resort community. Situated on a premium lot with stunning water view, this fully furnished property is perfect as a luxury vacation retreat or a high-performing short-term rental investment.
$720,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
57Picture(s)
2,263Sqft
Beautiful fully furnished vacation home located in the highly desirable Windsor at Westside Resort. This property offers an open floor plan, private screened pool and spa, and access to world-class community amenities including clubhouse, resort-style pool, fitness center, playground, and sports courts. Zoned for short-term rental, making it ideal for investors or as a second home.
$445,000
Residential
KISSIMMEE, Florida 34747
7Bedroom(s)
5Bathroom(s)
37Picture(s)
3,314Sqft
Welcome to this stunning 7-bedroom, 5-bathroom pool home situated on a spacious corner lot in the highly sought-after Windsor at Westside Resort. Ideal for large families, multi-generational living, or short-term rental investment, this beautifully maintained home combines comfort, style, and resort-style amenities in a gated community just minutes from Disney and major attractions.
$579,000
Residential
KISSIMMEE, Florida 34747
8Bedroom(s)
6Bathroom(s)
46Picture(s)
4,041Sqft
Welcome to this stunning 8-bedroom, 6-bathroom vacation home located in the highly desirable resort community of Windsor at Westside. Built in 2019, this turn-key property features the same spacious floor plan as the most sought-after models in the community and comes fully furnished and professionally decorated to maximize short-term rental income.
$679,000
Residential
KISSIMMEE, Florida 34747
7Bedroom(s)
5Bathroom(s)
67Picture(s)
3,281Sqft
INVESTOR ALERT — NOW $550,000! TURNKEY 7-BEDROOM SHORT-TERM RENTAL | WINDSOR AT WESTSIDE | PRIVATE POOL | MINUTES TO DISNEY
7 BEDROOMS. 5+ BATHROOMS. 3,281 SQ. FT. FULLY FURNISHED. NOW $550,000.
Investors looking for a large, turnkey vacation rental in the Disney-area market should take a serious look at 1861 Nice Court in Windsor at Westside Resort.
$550,000
Residential
KISSIMMEE, Florida 34747
6Bedroom(s)
4Bathroom(s)
53Picture(s)
3,142Sqft
Fully Furnished Pool and Spa Home. A fantastic choice to be your Vacation Home or Rental Property in the Windsor at Westside Resort! 6 Bedrooms - 4.5 Bathrooms and a Gorgeous Loft. Private Heated Pool and Spa with a great view from your pool deck area. As you step inside, you are greeted by a foyer and entrance high ceiling.
$510,000
Residential
KISSIMMEE, Florida 34747
6Bedroom(s)
4Bathroom(s)
23Picture(s)
3,142Sqft
Great, great price improvement!! It is really priced to sell quickly!! Beautiful 6 bedroom 4 1/2 bathroom, hideaway open floor plan on a corner lot in the desirable Windsor at Westside Community. Spacious great room over looking the screened 30 x 20 pool deck with heater pool and heated spa. First and second floor Master Suites.
$540,000
Residential
KISSIMMEE, Florida 34747
5Bedroom(s)
4Bathroom(s)
61Picture(s)
2,263Sqft
This is Windsor at Westside, your new home far from home! This beautiful townhouse features an amazing living room facing the desired pool you crave to see after a day of all the parks fun! INVESTMENT, this is the name of the game, this house has still books to come, which means money in your pocket. Upstairs, you will find 4 bedrooms with decorations ready to go.
$460,000
Residential
KISSIMMEE, Florida 34747
9Bedroom(s)
6Bathroom(s)
23Picture(s)
4,396Sqft
Luxury Villa – “Lord of the Manor” – Minutes from Disney
Experience elevated comfort and themed luxury at “Lord of the Manor,” a fully renovated 9-bedroom, 6-bathroom villa located just 8 miles from Disney.
$749,000
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).