248 Cheshire CourtKissimmee, FL, 34758

4beds

2baths

1,695sqft

Single Family Residence

Built in 2022

$90 Annually HOA Fee

$289,900

For sale

$329,950−$40,050 (12%)

Price per sqft: $171
Days on market: 535
Listed: May 5, 2025
Last reduction: −$9,600; Sep 3, 2026

MLS #S5126291Updated Oct 19, 2026

About this property

Virtually Staged. Spacious 4-Bedroom Retreat on a Quiet Cul-de-Sac – Your Kissimmee Dream Home Awaits!

Welcome to 248 Cheshire Court, a beautifully maintained home nestled on a peaceful cul-de-sac in the heart of Kissimmee. This charming 4-bedroom, 2-bathroom property offers a spacious open layout with plenty of natural light, perfect for comfortable family living and entertaining. Enjoy a modern kitchen with ample cabinetry, a generous master suite with a private bath, and a large backyard — ideal for outdoor relaxation or weekend BBQs. Conveniently located near schools, shopping, dining, and major roadways for an easy commute to Orlando and nearby attractions.

Don’t miss your chance to own this move-in-ready gem — schedule your private tour today!

Photos are of a model home that is very similar. Not actual home.

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Property details

Property type: Single Family Residence
Street address: 248 Cheshire Court
City: Kissimmee
State: FL
ZIP code: 34758
Year built: 2022
New construction: No
Faces: Northwest
Rooms: 6
Living area: 1,695 sqft
Total building area: 2,111 sqft
Architectural style: Traditional, Contemporary
Levels: One

The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 20, 2026 at 8:01 AM EDT

Price & sale history

Asking price reduced by $40,050 (12.1%) since first listed.

Date	Event	Price	Change from previous recorded asking price
Sep 3, 2026	Price reducedSep 3, 2026MLS #S5126291	$289,900Change: −12.1%−$40,050	−12.1%−$40,050
May 5, 2025	Listed for saleMay 5, 2025MLS #S5126291	$329,950	Not applicable