Windsor At Westside Real Estate

Welcome to Windsor At Westside, a premier subdivision located in the heart of Kissimmee, FL. This upscale community offers a perfect blend of luxury living and convenience, making it an ideal choice for those seeking a vibrant and modern lifestyle.

Situated in Osceola County, Windsor At Westside is known for its beautiful homes, resort-style amenities, and close proximity to top-rated schools, shopping centers, and entertainment options. Residents here enjoy easy access to major highways, making it a breeze to explore all that Central Florida has to offer.

Whether you're looking for a spacious single-family home or a stylish townhouse, Windsor At Westside has a range of housing options to suit every need and budget. The community features lush landscaping, walking trails, a clubhouse, fitness center, and a stunning pool area, providing plenty of opportunities for relaxation and recreation right at your doorstep.

With its convenient location, upscale amenities, and family-friendly atmosphere, Windsor At Westside is more than just a place to live – it's a place to call home. Come discover the perfect blend of comfort and style in this sought-after subdivision in Kissimmee, FL.

Newest Listings in Windsor At Westside

2105 Malta Terrace, Kissimmee $699,000

Welcome to this stunning 8-bedroom, 6-bathroom vacation home in the highly sought-after Windsor at Westside gated resort community just 2.5 miles from Walt Disney World. ...

8 Beds
6 Baths
Windsor At Westside SubDv.
34747 Zip Code

2440 Tangier Drive, Kissimmee $525,000

Located within the highly sought-after Windsor at Westside gated resort community, this fully furnished home offers flexibility as a primary residence, vacation getaway, ...

5 Beds
4 Baths
Windsor At Westside SubDv.
34747 Zip Code

8812 Macapa Drive, Kissimmee $680,000

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 West...

8 Beds
6 Baths
Windsor At Westside SubDv.
34747 Zip Code

8904 Prague Way, Kissimmee $515,000

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 co...

5 Beds
4 Baths
Windsor At Westside SubDv.
34747 Zip Code

8899 Geneve Ct, Kissimmee — 8899 $394,900 ▼

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 re...

4 Beds
4 Baths
Windsor At Westside SubDv.
34747 Zip Code

1857 Nice Court, Kissimmee $489,000 ▼

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 ...

5 Beds
4 Baths
Windsor At Westside SubDv.
34747 Zip Code

1885 Nice Court, Kissimmee $559,000

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 f...

6 Beds
5 Baths
Windsor At Westside SubDv.
34747 Zip Code

1909 Majorca Drive, Kissimmee — 1909 $424,999 ▼

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 res...

5 Beds
5 Baths
Windsor At Westside SubDv.
34747 Zip Code

2015 Majorca Drive, Kissimmee — Windsor At Westside $412,900

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 o...

5 Beds
5 Baths
Windsor At Westside SubDv.
34747 Zip Code

1861 Nice Ct, Kissimmee $550,000 ▼

INVESTOR ALERT — NOW $550,000! TURNKEY 7-BEDROOM SHORT-TERM RENTAL | WINDSOR AT WESTSIDE | PRIVATE POOL | MINUTES TO DISNEY 7 BEDROOMS. 5+ BATHROOMS. 3,281 SQ. FT. FUL...

7 Beds
6 Baths
Windsor At Westside SubDv.
34747 Zip Code

2183 Tripoli Ct, Kissimmee $659,000 ▼

This spacious fully furnished 9-bedroom, 6-bathroom pool home is located in the sought-after Windsor at Westside Resort. One of the largest floor plans in the community,...

9 Beds
6 Baths
Windsor At Westside SubDv.
34747 Zip Code

8944 Sydney Avenue, Kissimmee — Pulte Homes $399,900 ▼

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 mi...