David Shippey
863.521.4517

Kissimmee FL Gated Community Homes For Sale

Kissimmee FL Gated Community Real Estate listings are included below. These homes for sale in Kissimmee Florida are updated every day from our local MLS. If you would like to schedule a showing or have any questions about any of these Kissimmee FL gated community homes, please call David at 863-521-4517 or just click the "Schedule a Showing" or "Request More Info" button on any property detail pages.

Click Here to Create a Free Profile to Gain Access to Detailed MLS Information that only real estate agents have access to. Your Free Profile also enables you to save your favorite search's and homes.

Modify Search Criteria

Displaying results 1161-1170 of 1268
38 Photos 8833 Corcovado Drive Kissimmee, FL 34747

8833 Corcovado Drive
Kissimmee, FL 34747
Windsor At Westside Ph 2b
Residential

MLS# O6275641 / Active
9 Beds, 6.00 Total Baths, 6 Full Bath, 4391 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 2b

One or more photo(s) has been virtually staged. Investors, this home can be used for both Long Term and Short Term rentals! Big price reduction, be... 

More Details

$699,900
Provided courtesy of REDFIN CORPORATION
41 Photos 8844 Corcovado Drive Kissimmee, FL 34747

8844 Corcovado Drive
Kissimmee, FL 34747
Windsor At Westside Ph 2b
Residential

MLS# O6247686 / Active
8 Beds, 6.00 Total Baths, 6 Full Bath, 4041 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 2b

Sales Opportunity, HUGE REDUCTION!! Welcome prospective Buyers to appreciate this expansive 8-bedroom, 6-bathroom residence fully furnished and rea... 

More Details

$799,000
Provided courtesy of REALTY ONE GROUP EVOLUTION
88 Photos 1603 Lima Avenue Kissimmee, FL 34747

1603 Lima Avenue
Kissimmee, FL 34747
Windsor At Westside Ph 2b
Residential

MLS# G5089439 / Active
9 Beds, 6.00 Total Baths, 6 Full Bath, 4391 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 2b

Step into this fully furnished 9-bedroom, 6-bathroom gem designed to create unforgettable memories for families, business retreats, and vacationers... 

More Details

$799,999
Provided courtesy of EXP REALTY LLC
33 Photos 8887 Geneve Court Kissimmee, FL 34747

8887 Geneve Court
Kissimmee, FL 34747
Windsor At Westside Ph 2b
Residential

MLS# O6295445 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 2265 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 2b

Stunning, FULLY FURNISHED home located in the much sought after gated community of Windsor at Westside. This beautiful home is meticulously furnish... 

More Details

$435,000
Provided courtesy of ORLANDO REGIONAL PROPERTY MANAGEMENT
54 Photos 1614 Lima Avenue Kissimmee, FL 34747

1614 Lima Avenue
Kissimmee, FL 34747
Windsor At Westside Ph 2b
Residential

MLS# S5126817 / Active
8 Beds, 6.00 Total Baths, 6 Full Bath, 4041 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 2b

Spacious 8-bedroom, 6-bathroom single-family home located in the gated community Windsor at Westside Resort. This two-story home offers a functiona... 

More Details

$679,990
Provided courtesy of FLORIDA SPIRIT HOMES
56 Photos 8924 Bengal Court Kissimmee, FL 34747

8924 Bengal Court
Kissimmee, FL 34747
Windsor At Westside Ph 2b
Residential

MLS# O6304915 / Active
9 Beds, 6.00 Total Baths, 6 Full Bath, 4391 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 2b

Short Sale. TURNKEY 9 BEDROOM | 6 BATH | POOL HOME | CORNER LOT | SHORT-TERM RENTAL ZONED | FULLY FURNISHED - WINDSOR AT WESTSIDE- Investor-ready a... 

More Details

$710,900
Reduced -$9,000
Provided courtesy of KELLER WILLIAMS LEGACY REALTY
51 Photos 1586 Lima Avenue Kissimmee, FL 34747

1586 Lima Avenue
Kissimmee, FL 34747
Windsor At Westside Ph 2b
Residential

MLS# O6210246 / Active
8 Beds, 6.00 Total Baths, 6 Full Bath, 4041 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 2b

Experience luxury living in this beautiful 8-bedroom, 6-bathroom vacation home located in the resort-style community of Windsor at Westside. The sp... 

More Details

$630,000
Reduced -$30,000
Provided courtesy of BAY STREET GROUP FLORIDA LLC
48 Photos 2428 Dubai Street Kissimmee, FL 34747

2428 Dubai Street
Kissimmee, FL 34747
Windsor At Westside Ph 3
Residential

MLS# O6233761 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 2263 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 3

Nestled Townhouse in Windsor at Westside, one of Kissimmee's premier short-term rental communities, this FULLY FURNISHED townhouse is your oasis of... 

More Details

$498,000
Provided courtesy of FLORIDA CONNEXION PROPERTIES
34 Photos 8936 Sydney Avenue Kissimmee, FL 34747

8936 Sydney Avenue
Kissimmee, FL 34747
Windsor At Westside Ph 3
Residential

MLS# S5122126 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 2263 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 3

Beautiful house, with heated pool, barbecue, richly furnished and decorated, containing 5 suites and 4.5 bathrooms, offering accommodation for 11 p... 

More Details

$498,000
Provided courtesy of MACKEN REALTY INC
81 Photos 2432 Tangier Drive Kissimmee, FL 34747

2432 Tangier Drive
Kissimmee, FL 34747
Windsor At Westside Ph 3
Residential

MLS# O6299100 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 2263 Sqft
Area: 34747 - Kissimmee/celebration, Subdivision: Windsor At Westside Ph 3

**New Improved Price!** Live the RESORT LIFESTYLE every day or generate EXCEPTIONAL SHORT-TERM RENTAL income with this STUNNING 5-bedroom, 4.5-bath... 

More Details

$474,000
Provided courtesy of EXP REALTY LLC

Broker Reciprocity The information being provided by © 2025 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 07-22-2025 2:00 AM EST.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions

The gated community homes above are brought to you by David Shippey REALTOR®.

Not finding what you are looking for? View all Kissimmee Homes for Sale here.

Related Searches

Gated Community Kissimmee Florida Homes For Sale.
Kissimmee Florida Gated Community Homes.
Gated Community Kissimmee FL Houses For Sale.
Gated Community Kissimmee FL Houses.