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

6Bedroom(s)
4Bathroom(s)
57Picture(s)
3,142Sqft
Welcome to resort-style living at its finest in the highly sought-after Windsor at Westside Resort! This beautifully maintained 6-bedroom, 4.5-bath pool home is offered fully furnished and turnkey, making it the perfect opportunity for a vacation home, investment property, or even a full-time residence just minutes from Walt Disney World and Central Florida's most popular attractions.
$559,000
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Residential

KISSIMMEE, Florida 34747

6Bedroom(s)
4Bathroom(s)
43Picture(s)
3,142Sqft
Just reduced $25,000! PRICED BELOW MARKET VALUE. This fully furnished property with EV station is within walking distance of the clubhouse. Rental-ready 6-bedroom property is priced to move fast and generate income from day one.
$495,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
36Picture(s)
2,263Sqft
Welcome to your slice of paradise at Windsor at Westside! Fully furnished and Airbnb-ready, this spacious 5-bedroom, 4.5-bath townhome with a private pool is located in one of Greater Orlando’s most sought-after short-term rental communities. Designed to comfortably accommodate 14+ guests, this property is ideal as both a personal getaway and an income-producing investment.
$412,900
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
40Picture(s)
2,265Sqft
Priced to sell! This stunning home sits in the third and newest phase of the sought-after Windsor at Westside Resort, with also a Private Heated Pool. Featuring 5 bedrooms and 4 bathrooms, it offers the perfect blend of fun and relaxation.
$428,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
40Picture(s)
2,263Sqft
TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one.
$419,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
31Picture(s)
2,265Sqft
TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| END UNIT Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one.
$449,000
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Residential

KISSIMMEE, Florida 34747

8Bedroom(s)
6Bathroom(s)
83Picture(s)
4,041Sqft
Welcome to this exceptional 8-bedroom, 6-bathroom resort home in the highly desirable Windsor at Westside community, where stunning pond views, privacy, and resort-style amenities come together to create the ultimate Central Florida retreat. Offered fully furnished and professionally equipped for short-term rentals, this turnkey property is ready for immediate enjoyment or income generation.
$570,000
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Residential

KISSIMMEE, Florida 34747

6Bedroom(s)
4Bathroom(s)
49Picture(s)
3,142Sqft
Escape to this exceptional vacation retreat located within the popular Windsor at Westside Resort, one of Central Florida’s premier resort communities. Offering 3,142 square feet of thoughtfully designed living space, this spacious home combines comfort, privacy, and convenience just minutes from Orlando’s world-famous attractions.
$490,000
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Residential

KISSIMMEE, Florida 34747

7Bedroom(s)
5Bathroom(s)
34Picture(s)
3,314Sqft
Welcome to this exceptional 7-bedroom, 5-bathroom vacation home located in the highly desirable Windsor at Westside Resort. This fully furnished property is turn-key and revenue-ready, offering a spacious and well-designed floor plan ideal for large families and short-term rental guests.
$720,000
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Residential

KISSIMMEE, Florida 34747

8Bedroom(s)
6Bathroom(s)
54Picture(s)
4,041Sqft
Spacious 8-bedroom, 6-bathroom single-family home located in the gated community Windsor at Westside Resort. This two-story home offers a functional layout with an open-concept living and dining area, as well as a well-appointed kitchen featuring granite countertops, stainless steel appliances, and a large island for additional workspace.
$639,900
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Residential

KISSIMMEE, Florida 34747

4Bedroom(s)
3Bathroom(s)
33Picture(s)
2,263Sqft
INCOME-PRODUCING OPPORTUNITY in Windsor at Westside, one of Kissimmee’s most sought-after short-term rental communities near Orlando’s world-famous theme parks. Unlike many investment properties in the area, this FULLY FURNISHED and TURNKEY 4-bedroom, 3.
$416,999
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Residential

KISSIMMEE, Florida 34747

7Bedroom(s)
5Bathroom(s)
58Picture(s)
3,314Sqft
Experience the ultimate Orlando getaway in this beautifully appointed 7-bedroom, 5.5-bath vacation home located in the highly desirable Windsor at Westside Resort, just minutes from Walt Disney World and Central Florida’s top attractions.
$589,000
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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!