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)
43Picture(s)
2,263Sqft
Priced to Sell! Where else can you live in Florida feeling like you are on Vacation everyday?! Resort style pools, Lazy River, Water Playground, Fitness Center, Restaurant & Club House, Pond and Pier and so much more! Those are just the amenities; lets talk about this 5 Bedroom & 5 Bath with a private garage in paradise.
$390,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
53Picture(s)
2,492Sqft
Located within the highly sought-after Windsor at Westside gated resort community, this fully furnished home offers flexibility as a primary residence, vacation getaway, or income-producing short-term rental. The property is already set up for Airbnb use and is being sold turnkey, allowing for immediate occupancy or continued rental operations.
$525,000
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Residential

KISSIMMEE, Florida 34747

8Bedroom(s)
6Bathroom(s)
90Picture(s)
4,041Sqft
Discover an exceptional opportunity to own this beautifully furnished 8-bedroom, 6-bathroom pool home in the highly sought-after GATED resort community of Windsor at Westside.
$680,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
60Picture(s)
2,492Sqft
Welcome to this stunning 5-bedroom, 4-bathroom home located in the highly desirable gated community of Windsor at Westside in Kissimmee. This spacious residence offers approximately 2,492 square feet of beautifully designed living space with an open-concept floor plan, perfect for entertaining family and guests.
$549,990
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
61Picture(s)
2,492Sqft
Located in one of Central Florida's premier resort communities, this beautifully maintained and fully furnished 5-bedroom, 4-bath pool home offers the perfect blend of comfort, style, and convenience.
$515,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
40Picture(s)
2,265Sqft
Welcome to one of the best-located homes in Windsor at Westside Resort! Situated on a premium corner lot and just steps from the clubhouse, this fully furnished 5-bedroom, 4.5-bathroom townhome offers one of the closest walkable locations to the resort’s incredible amenities, making it especially desirable for vacation guests and short-term rental success.
$424,900
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Residential

KISSIMMEE, Florida 34747

4Bedroom(s)
3Bathroom(s)
30Picture(s)
2,102Sqft
Welcome to Windsor at Westside—one of Central Florida's premier resort communities and one of the most sought-after destinations for vacation homeowners and short-term rental investors. This beautifully furnished 4-bedroom, 3.5-bathroom townhome combines exceptional guest appeal with thoughtful upgrades, a private pond view, and a proven rental history.
$394,900
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Residential

KISSIMMEE, Florida 34747

6Bedroom(s)
4Bathroom(s)
15Picture(s)
3,142Sqft
Welcome to the ultimate Florida lifestyle in the highly desirable guard-gated community of winsor at westsite! This stunning, professionally decorated 6 bedroom, 5 bath pool single family house is fully furnished and move-in ready.
$499,900
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Residential

KISSIMMEE, Florida 34747

8Bedroom(s)
6Bathroom(s)
48Picture(s)
4,041Sqft
Take a look at this unique amazing property at 1941 Nice Ct located in Windsor Westside, one of Disney’s most popular short term rental vacation home communities. This incredible pool home features 8 bedrooms,6 bathrooms, and is going to quickly become your favorite getaway destination. Enjoy and relax in the living room that overlooks the pool.
$670,000
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Residential

KISSIMMEE, Florida 34747

8Bedroom(s)
6Bathroom(s)
30Picture(s)
4,041Sqft
Welcome to 8824 Bengal Court, a FULLY FURNISHED 8-BEDROOM, 6-BATHROOM home in the prestigious GUARD-GATED WINDSOR AT WESTSIDE RESORT. Built in 2019, this exceptional property is ideal as a PRIMARY RESIDENCE, VACATION HOME, or INCOME-PRODUCING SHORT-TERM RENTAL, offering luxury, versatility, and resort-style living.
$570,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
44Picture(s)
2,492Sqft
Welcome to a fantastic investment opportunity in the Windsor at Westside resort community! This fully furnished 5-bedroom, 4-bathroom pool home offers a luxurious living space with great rental potential, perfect for investors.
$489,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
74Picture(s)
2,263Sqft
Fully Furnished 5-Bedroom Townhome with Heated Private Pool in Prime Kissimmee Location Welcome to this exceptional two-story townhome in the heart of Kissimmee, offering the perfect combination of comfort, style, and investment potential.
$465,000
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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!