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)
20Picture(s)
2,263Sqft
Welcome to this spacious 5-bedroom, 4.5-bathroom townhome in the Windsor at Westside community. This approximately 2,263-square-foot home is FULLY FURNISHED and features an open floor plan, a well-appointed kitchen, comfortable living areas, and a PRIVATE POOL WITH A POOL HEATING SYSTEM. The home has NEWLY INSTALLED VINYL FLOORING.
$415,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
20Picture(s)
2,265Sqft
Short Sale. PREMIUM CORNER LOT | FULLY FURNISHED | PRIVATE POOL | BUILT IN 2020! **SHORT-SALE PRE APPROVED BY BANK** Welcome to this beautiful 5-bedroom, 4.
$389,900
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
20Picture(s)
2,263Sqft
YOUR FLORIDA VACATION HOME AND INVESTMENT OPPORTUNITY AWAITS! Discover the perfect combination of comfort, convenience, and resort-style living in the highly desirable, guard-gated community of Windsor at Westside! This fully furnished 5-bedroom, 4.
$380,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
20Picture(s)
2,263Sqft
This stunning retreat 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, offers the perfect blend of comfort and sophistication.
$449,990
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
20Picture(s)
2,263Sqft
Resort Living for Every Lifestyle, In Windsor, Near Disney: Short-Term Rental, Long-Term Rental, or Primary Home. Discover an exciting opportunity at 1965 Majorca Drive, a spacious five-bedroom, 4.5-bath townhome, with a 1-car garage in the sought-after Windsor at Westside resort community in Kissimmee.
$437,500
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Residential

KISSIMMEE, Florida 34747

9Bedroom(s)
6Bathroom(s)
20Picture(s)
4,391Sqft
WATER VIEWS, RESORT AMENITIES & YOUR OWN PRIVATE POOL! Welcome to this 9-bedroom, 6-bathroom fully furnished home in the highly desirable gated resort community of Windsor at Westside. With plenty of room to gather, entertain, and unwind, this home captures the Florida vacation lifestyle.
$680,000
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Residential

KISSIMMEE, Florida 34747

4Bedroom(s)
3Bathroom(s)
20Picture(s)
2,102Sqft
Your Florida vacation home—and investment opportunity—just minutes from Disney! Welcome to this beautifully furnished 4-bedroom, 3.5-bath pool townhome in the highly sought-after Windsor at Westside Resort, where resort-style living, flexible short-term rental potential, and an outstanding Central Florida location come together.
$415,000
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Residential

KISSIMMEE, Florida 34747

9Bedroom(s)
6Bathroom(s)
20Picture(s)
4,391Sqft
Discover an exceptional blend of luxury, comfort, and investment potential in this fully furnished 9-bedroom, 6-bathroom lakefront residence. Turnkey and approved for short-term rentals, this impressive property presents an exciting opportunity for investors seeking a vacation rental property or buyers dreaming of a spacious Florida retreat.
$678,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
20Picture(s)
2,265Sqft
Welcome to this beautifully appointed 5-bedroom, 4.5-bathroom townhome in the heart of Kissimmee, just minutes from Central Florida's world-famous attractions, shopping, dining, and entertainment.
$389,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
20Picture(s)
2,263Sqft
Turnkey, income-ready vacation home in Windsor at Westside, a gated resort community in Kissimmee and one of the area’s most popular destinations for short-term rentals. This fully furnished 5-bedroom, 4.5-bath residence combines resort-style living with proven guest appeal, making it an exceptional opportunity for investors and second-home buyers alike.
$409,990
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
20Picture(s)
2,265Sqft
Your Florida getaway starts here! This fully furnished 5-bedroom, 4.5-bathroom end-unit townhome in gated Windsor at Westside combines a private pool, peaceful conservation views, and access to resort amenities near Disney. With 2,265 square feet of living space, there’s room to gather, unwind, and enjoy time together.
$399,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
42Picture(s)
2,263Sqft
Welcome to this beautifully maintained 5-bedroom, 4.5-bathroom two-story townhouse located in the sought-after resort community of Windsor at Westside in Kissimmee. The main level welcomes you with a spacious bedroom and full bathroom on the left, followed by a bright and open layout connecting the kitchen, dining area, and living room—perfect for entertaining or relaxing.
$419,000
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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!