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!

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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
33Picture(s)
2,265Sqft
Stunning, FULLY FURNISHED home located in the much sought after gated community of Windsor at Westside. This beautiful home is meticulously furnished and beautifully decorated. It also boasts 5 bedrooms, and 4.5 bathrooms, an open floor concept, a large fully equipped kitchen with granite countertops, stainless-steel appliances, and an island kitchen linked to the family room and dining room.
$395,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
52Picture(s)
2,263Sqft
Incredible opportunity in the highly sought-after Windsor at Westside Resort! This fully furnished five bedroom, four and a half bathroom retreat comfortably accommodates up to 16 guests and is ideally located just minutes from Orlando’s world famous theme parks and attractions.
$387,500
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
35Picture(s)
2,492Sqft
Your Dream Vacation Home—Just Minutes from Disney! Imagine owning a fully furnished 5-bedroom home in one of Kissimmee’s most sought-after resort communities—Windsor at Westside—just minutes from the magic of Disney and the excitement of US-192. Surrounded by restaurants, shops, theme parks, and unforgettable experiences, this could all be yours.
$482,900
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
54Picture(s)
2,263Sqft
Step into this stunning and beautifully furnished 5-bedroom, 4-bathroom townhome nestled within an exclusive resort-style community. Designed with comfort and style in mind, this spacious home offers a modern layout perfect for families. Enjoy your own private pool, ideal for relaxing afternoons or entertaining in the Florida sun.
$399,900
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
78Picture(s)
2,265Sqft
Dive headfirst into paradise at 2427 Dubai Street, Windsor At Westside! Forget ordinary – this is your resort, a dazzling, delivering a 6.9% Cap rate to the current owner is this fully furnished 5-bedroom, 4.5-bathroom end unit townhome where luxury meets pure, unadulterated fun. Imagine: sun-kissed mornings by your private, screened-in pool, the cool water shimmering like a sapphire.
$408,000
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Residential

KISSIMMEE, Florida 34747

8Bedroom(s)
6Bathroom(s)
30Picture(s)
4,041Sqft
Welcome to the best of Florida resort life! This 8 bedroom 6 bathroom house has all you can ask for and more! Fully furnished, this home is ready for an immediate occupancy, whether you're seeking an ideal AirBNB/Short-Term Rental or a personal vacation/ winter time residence.
$699,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
62Picture(s)
2,263Sqft
Nestled Townhouse in Windsor at Westside, one of Kissimmee's premier short-term rental communities, this FULLY FURNISHED townhouse is your oasis of luxury and relaxation. With five spacious bedrooms and four and a half bathrooms, this stunning retreat offers the perfect blend of comfort and sophistication.
$419,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
28Picture(s)
2,263Sqft
GREAT, GREAT PRICE IMPROVEMENT!! This beautiful home is locate on the third and newest phase of the sought after Windsor at Westside Resort.
$499,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
100Picture(s)
2,263Sqft
*** INCOME POTENTIAL *** VACATION HOME FULLY FURNISHED. In Excellent condition and beautifully decorated this 5 Bedroom Townhome with a splash pool has all you need for spending great moments in the Orlando Area or renting it out when not using it. It offers great income potential.
$490,000
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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).

Speak to one of our Central Florida Real Estate Specialists Today!