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 OLDSMAR
  • Built in 1987
  • MLS® #: TB8513297
  • 3 Bedrooms
  • 2 Full baths
  • 1,688 SqFt
Active
  • Located in WINTER HAVEN
  • Built in 1967
  • MLS® #: P4934907
  • 3 Bedrooms
  • 3 Full baths
  • 3,885 SqFt
Active
  • Located in NORTH VENICE
  • Built in 2004
  • MLS® #: N6144050
  • 3 Bedrooms
  • 2 Full baths
  • 2,262 SqFt
Active
  • Located in GAINESVILLE
  • Built in 2017
  • MLS® #: GC538735
  • 3 Bedrooms
  • 3 Full baths
  • 2,079 SqFt
Active
  • Located in BRADENTON
  • Built in 1959
  • MLS® #: A4686059
  • 2 Bedrooms
  • 2 Full baths
  • 460 SqFt
Active
  • Located in UNIVERSITY PARK
  • Built in 1994
  • MLS® #: A4696012
  • 2 Bedrooms
  • 2 Full baths
  • 1,735 SqFt
Active
  • Located in ORLANDO
  • Built in 2014
  • MLS® #: O6412846
  • 3 Bedrooms
  • 2 Full baths
  • 2,984 SqFt
Active
  • Located in WINTER HAVEN
  • Built in 1982
  • MLS® #: P4938946
  • 4 Bedrooms
  • 3 Full baths
  • 2,056 SqFt
Active
  • Located in PARRISH
  • Built in 2025
  • MLS® #: A4695899
  • 4 Bedrooms
  • 3 Full baths
  • 2,500 SqFt
Active
  • Located in ODESSA
  • Built in 2021
  • MLS® #: TB8510897
  • 3 Bedrooms
  • 2 Full baths
  • 1,612 SqFt
Active
  • Located in OSPREY
  • Built in 1981
  • MLS® #: A4694878
  • 3 Bedrooms
  • 2 Full baths
  • 1,859 SqFt
Active
  • Located in SANFORD
  • Built in 1985
  • MLS® #: O6408418
  • 2 Bedrooms
  • 2 Full baths
  • 975 SqFt
Active
  • Located in CLEARWATER
  • Built in 1978
  • MLS® #: TB8511541
  • 2 Bedrooms
  • 2 Full baths
  • 980 SqFt
Active
  • Located in CLEARWATER
  • Built in 1972
  • MLS® #: TB8506548
  • 4 Bedrooms
  • 2 Full baths
  • 1,380 SqFt
Active
  • Located in PLACIDA
  • Built in 2025
  • MLS® #: C7525099
  • 3 Bedrooms
  • 2 Full baths
  • 2,118 SqFt
Active
  • Located in PORT ORANGE
  • Built in 2004
  • MLS® #: V4948529
  • 4 Bedrooms
  • 2 Full baths
  • 1,988 SqFt
Active
  • Located in PORT CHARLOTTE
  • Built in 2020
  • MLS® #: C7524293
  • 3 Bedrooms
  • 2 Full baths
  • 1,563 SqFt
Active
  • Located in PORT CHARLOTTE
  • Built in 1983
  • MLS® #: C7524217
  • 2 Bedrooms
  • 1 Full bath
  • 908 SqFt
Active
  • Located in NORTH PORT
  • Built in 2020
  • MLS® #: C7524109
  • 3 Bedrooms
  • 2 Full baths
  • 1,574 SqFt
Active
  • Located in AUBURNDALE
  • Built in 2025
  • MLS® #: O6391621
  • 3 Bedrooms
  • 2 Full baths
  • 1,435 SqFt

Last Updated: 2026-06-06T11:43:27.21863Z