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)
89Picture(s)
2,263Sqft
Discover the pinnacle of Florida living in this stunning, fully furnished 5-bedroom, 4.5-bathroom townhome, nestled within the highly sought-after Windsor at Westside resort community.
$424,999
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KISSIMMEE, Florida 34747

7Bedroom(s)
5Bathroom(s)
48Picture(s)
3,314Sqft
Location, location!!!!This fully furnished, turn-key 7-bedroom, 5.5-bathroom home offers 3,314 sq ft at Windsor at Westside a Gated Community.
$575,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
44Picture(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.
$445,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
5Bathroom(s)
77Picture(s)
2,622Sqft
Spacious 5-bedroom, 5.5-bathroom pool home located just 8 miles from Walt Disney World. This open-concept property features a modern kitchen equipped with stainless steel appliances, granite countertops, and a large island overlooking the dining and living areas. The floor plan includes a convenient primary suite on the main level.
$565,000
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Residential

KISSIMMEE, Florida 34747

9Bedroom(s)
6Bathroom(s)
47Picture(s)
4,391Sqft
The largest home on one of the best lots in entire Windsor at Westside resort. Equipped with brand new HVAC system for upstairs, this fully furnished/equipped home with private pool deck, is just stone throw away from fabulous clubhouse and resort amenities. Brand new Duralux water proof flooring throughout second floor and ground floor bedrooms. UPGRADED CABINETRY throughout.
$658,000
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
24Picture(s)
2,263Sqft
MAJOR PRICE IMPROVEMENT — TURNKEY, FULLY FURNISHED 5-BEDROOM POOL HOME IN WINDSOR AT WESTSIDE! Welcome to 2410 Tangier Drive, a beautifully maintained and fully furnished 5-bedroom, 4.5-bath townhome offering 2,263 sq. ft. in the highly desirable resort-style community of Windsor at Westside.
$399,900
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
35Picture(s)
2,492Sqft
FULLY FURNISHED | TURNKEY INVESTMENT | RESORT-STYLE COMMUNITY Welcome to this beautiful two-story home located in the highly desirable resort-style community of Windsor at Westside. Featuring 5 spacious bedrooms and 4 full bathrooms, this fully furnished property is move-in ready and perfectly suited as a primary residence, vacation home, or income-producing short-term rental.
$489,000
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KISSIMMEE, Florida 34747

4Bedroom(s)
3Bathroom(s)
52Picture(s)
2,102Sqft
Welcome to your ideal vacation home and income-producing property in the highly sought-after Windsor at Westside Resort! This beautifully appointed 4-bedroom, 3.5-bathroom townhome is fully furnished and turnkey, making it perfect for short-term rentals or a personal getaway. Step inside to find stylish décor throughout and an open-concept floor plan designed for comfort and entertaining.
$404,000
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Residential

KISSIMMEE, Florida 34747

7Bedroom(s)
5Bathroom(s)
42Picture(s)
3,314Sqft
7-Bedroom 5.5-Bathroom fully furnished home at Windsor at Westside a Gated Community. Located around 15 minutes from Disney World, Master Bedroom in the First Floor. Resort-Style Community. HOA covers, trash pick-up, lawn care, and grounds maintenance. New Laminate flooring in the Primary Bedroom Downstairs and all the Second Floor in 2026.
$699,900
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Residential

KISSIMMEE, Florida 34747

4Bedroom(s)
3Bathroom(s)
81Picture(s)
2,102Sqft
Welcome to 2022 Majorca Drive, a highly desirable 4-bedroom, 3.5-bathroom townhome located in the Windsor at Westside Resort.
$399,990
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Residential

KISSIMMEE, Florida 34747

5Bedroom(s)
4Bathroom(s)
26Picture(s)
2,492Sqft
A fantastic choice to be your Vacation Rental Property in the Windsor at Westside, located in Kissimmee Florida! 5 Bedrooms - 4 Bathrooms and your own Private Pool. Welcoming you inside is an amazing open floor concept that combines your living, dining and kitchen areas into one space. Also downstairs you will have an ensuite for your convenience.
$483,000
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Residential

KISSIMMEE, Florida 34747

6Bedroom(s)
4Bathroom(s)
25Picture(s)
3,142Sqft
Priced to sell! This fully furnished 6 bedroom, 4.
$655,000
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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!