Windsor at Westside Real Estate

Real Estate Listing in the Disney Area “Super Community”

The Best Windsor at Westside Real Estate Listings

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.

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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!

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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
18Picture(s)
2,263Sqft
Price adjustment! Awesome vacation home investment opportunity! This beautiful fully furnished home is located at the most sought-after Windsor at Westside Resort phase 3, completed just a couple years ago. The Resort is a gated community and includes great amenities such as clubhouse, gym, lazy river, tiki bar, restaurant, sand volleyball, and so on.
$545,900

Residential

8Bedroom(s)
6Bathroom(s)
40Picture(s)
4,041Sqft
This beautiful 8 bed, 6 bath vacation home in the popular Windsor at Westside Resort is being sold fully furnished and is tastefully decorated with many themed rooms, making it your perfect vacation home! Featuring an east facing pool deck that overlooks a pond you won't find a better view than this! With over 4000 square feet of living space there's plenty of room for entertaining and large famil
$919,000

Residential

5Bedroom(s)
5Bathroom(s)
39Picture(s)
2,622Sqft
Beautiful fully furnished 5 bed 5/2 bath in the desirable Windsor at Westside! Luxury vacation home with private pool.
$679,000

Residential

5Bedroom(s)
4Bathroom(s)
21Picture(s)
2,263Sqft
Come see this beautiful, almost new, vacation home. Offered fully furnished and decorated! This lovely 2-story townhome features 5 bedrooms, 4.5 baths and a loft upstairs. Best of all, this home features a private pool! Windsor amenities include a Clubhouse with fitness center and resort-style pool, on-site restaurant, arcade games room, playground, and concierge.
$579,000

Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
5Bathroom(s)
63Picture(s)
2,622Sqft
Very spacious 5 Bed , 5.5 Bath home located in Windsor at Westside Resort Community. The home is fully furnished and equipped with amazing decor.
$714,000

Residential

5Bedroom(s)
4Bathroom(s)
48Picture(s)
2,263Sqft
Amazing house in the desired Windsor at Westside near DISNEY! Future bookings can be conveyed to buyer! 24 hour guarded gate short term rental/VACATION community. Turn-key professional furnished. 5 bed 4.5 bath with one bedroom downstairs. Half bath next to pool in patio which is facing south. Upgraded cabinet and counter top.
$540,000

Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
43Picture(s)
2,263Sqft
This spacious 5 bedrooms 4.1 bath resort community home is located in desirable Windsor of Westside. Not only is the property centrally located to Disney World, and shopping and dining, it's also conveniently located across the street from the 5,000 sqft clubhouse which means all the luxuries of resort living are only a few steps away.
$545,000

Residential

KISSIMMEE, Florida 34747

9Bedroom(s)
6Bathroom(s)
16Picture(s)
4,391Sqft
This fully furnished vacation home internet, lawn maintenance and daily trash management including in the HOA. This immaculate, professionally-designed 2-story Home with a private pool invites comfort and exudes modern elegance. Windsor at Westside is one of Kissimmee’s most luxurious resort community.
$919,999

Residential

KISSIMMEE, Florida 34747

7Bedroom(s)
5Bathroom(s)
32Picture(s)
3,281Sqft
Don't miss out on this 7 BEDROOM 5 BATH Luxury VACATION HOME. This beautiful property built by Pulte homes comes fully furnished with professionally designed decor. This income producing property has upgraded granite counter tops, stainless steel appliances and tile throughout main living area. Beautiful screened pool area with paver deck, covered lanai and hot tub.
$719,000

Residential

KISSIMMEE, Florida 34747

9Bedroom(s)
6Bathroom(s)
42Picture(s)
4,391Sqft
The largest floor plan on one of the best lots in Fabulous Windsor at Westside resort. This fully furnished, professionally decorated home is situated on a rare greenbelt lot. South facing private pool deck backs to a nature preserve, this home is just stone throw's away from resort clubhouse and amenities.
$985,000
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