Windsor At Westside

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Windsor at Westside

About Windsor at Westside:

Windsor at Westside consists of elegant and luxurious townhomes and single-family homes ranging from four to nine bedrooms. Windsor at Westside is in a peaceful and tranquil location, still close to all of the famous Central Florida attractions. Windsor at Westside is a gated resort community with an array of amenities for you to enjoy. Many of the Windsor at Westside homes offer private pools with a screened-in area for you to soak up the Florida sunshine.

Location:

Windsor at Westside is located in Kissimmee, FL, off the main roads in a quiet residential area. The Westside community is close to Walt Disney World, Universal Studios, and Orlando’s other world-class theme parks. The US-192 has a selection of restaurants, gift shops, bars, and grocery stores, a short drive from the neighborhood. The US-192 gives easy access to the Walt Disney World attractions and the Interstate 4 for you to explore everything else Orlando has to offer.

Amenities:

Windsor at Westside homes are surrounded by an array of beautiful resort-style amenities, with something for everyone you will never be bored! The Windsor at Westside Resort boasts an 8,000 square feet clubhouse with a market and deli, a video arcade, a sundries shop, and a state-of-the-art fitness center. The clubhouse is conveniently located close to the main gate, so it is central to most homes. Windsor at Westside Resort features two beautiful pool areas. A resort-style pool in a quieter location for adults and a zero-entry pool with a water splash zone for kids. Surrounding both pools is a paved sunbathing deck with ample sun loungers and poolside cabanas. A jacuzzi and luxurious lazy river are also set amidst the trees and foliage. For those wanting to burn off some steam, basketball courts and volleyball courts are available to enjoy as well as a covered children’s play area. Windsor at Westside also features Tu Casa Bar & Grill for those who wish to dine on-site.

Why should I purchase a home within Windsor at Westside?

Windsor at Westside Resort is a newer community with a prime location, so it is exceptionally appealing to those wanting to vacation in Orlando. This makes it a desirable community to purchase a second home and earn additional income through short-term rentals. The community is located just minutes from the most popular Orlando attractions and has some of the best resort-style amenities in the area. If you are interested in purchasing a second home to use as a short-term rental, browse our listings displayed below and contact us for more detailed information.

Active
  • Located in SARASOTA
  • Built in 1959
  • MLS® #: O6400956
  • 2 Bedrooms
  • 1 Full bath
  • 1,136 SqFt
Active
  • Located in DUNEDIN
  • Built in 1977
  • MLS® #: TB8498756
  • 2 Bedrooms
  • 2 Full baths
  • 965 SqFt
Active
  • Located in ORLANDO
  • Built in 1982
  • MLS® #: O6256076
  • 2 Bedrooms
  • 2 Full baths
  • 1,450 SqFt
Active
  • Located in WINTER HAVEN
  • Built in 2017
  • MLS® #: TB8491651
  • 4 Bedrooms
  • 2 Full baths
  • 2,526 SqFt
Active
  • Located in HUDSON
  • Built in 2002
  • MLS® #: W7877136
  • 3 Bedrooms
  • 2 Full baths
  • 1,176 SqFt
Active
  • Located in LAKELAND
  • Built in 1962
  • MLS® #: O6393554
  • 3 Bedrooms
  • 2 Full baths
  • 1,444 SqFt
Active
  • Located in SANFORD
  • Built in 2003
  • MLS® #: O6401281
  • 6 Bedrooms
  • 4 Full baths
  • 3,479 SqFt
Active
  • Located in DORADO
  • Built in 2007
  • MLS® #: PR9120806
  • 3 Bedrooms
  • 3 Full baths
  • 2,336 SqFt
Active
  • Located in ORLANDO
  • Built in 2018
  • MLS® #: O6401280
  • 3 Bedrooms
  • 2 Full baths
  • 1,461 SqFt
Active
  • Located in SOUTH PASADENA
  • Built in 1976
  • MLS® #: TB8500506
  • 2 Bedrooms
  • 2 Full baths
  • 1,045 SqFt
Active
  • Located in RIO GRANDE
  • Built in 2023
  • MLS® #: PR9120805
  • 3 Bedrooms
  • 3 Full baths
  • 3,381 SqFt
Active
  • Located in NOKOMIS
  • Built in 1997
  • MLS® #: A4690918
  • 2 Bedrooms
  • 2 Full baths
  • 1,516 SqFt
Active
  • Located in GAINESVILLE
  • Built in 1980
  • MLS® #: GC539686
  • 3 Bedrooms
  • 2 Full baths
  • 1,170 SqFt
Active
  • Located in PALM BAY
  • Built in 2026
  • MLS® #: O6401275
  • 3 Bedrooms
  • 2 Full baths
  • 1,782 SqFt
Active
  • Located in ORLANDO
  • Built in 1999
  • MLS® #: O6401274
  • 2 Bedrooms
  • 2 Full baths
  • 1,120 SqFt
Active
  • Located in BRADENTON
  • Built in 2000
  • MLS® #: A4690915
  • 2 Bedrooms
  • 2 Full baths
  • 912 SqFt
Active
  • Located in ORLANDO
  • Built in 1987
  • MLS® #: O6401272
  • 3 Bedrooms
  • 2 Full baths
  • 1,106 SqFt
Active
  • Located in SUMMERFIELD
  • Built in 1996
  • MLS® #: O6401267
  • 3 Bedrooms
  • 2 Full baths
  • 1,188 SqFt
Active
  • Located in LARGO
  • Built in 1974
  • MLS® #: O6401266
  • 2 Bedrooms
  • 1 Full bath
  • 825 SqFt
Active
  • Located in THE VILLAGES
  • Built in 2004
  • MLS® #: G5111087
  • 2 Bedrooms
  • 2 Full baths
  • 1,132 SqFt

Last Updated: 2026-04-22T09:13:07.492467Z