248 Cheshire Ct Kissimmee, FL 34758
248 Cheshire Ct Kissimmee, FL 34758 | MLS S5126291 Photo 1
248 Cheshire Ct Kissimmee, FL 34758 | MLS S5126291 Photo 2
248 Cheshire Ct Kissimmee, FL 34758 | MLS S5126291 Photo 3
248 Cheshire Ct Kissimmee, FL 34758 | MLS S5126291 Photo 4
248 Cheshire Ct Kissimmee, FL 34758 | MLS S5126291 Photo 5
For more information on this listing, contact us at: (352) 871-7333
Active
$289,900

248 Cheshire Ct Kissimmee, FL 34758

Single Family Home Property Type
4 Beds
2 Baths
1,695 Sq. Ft.
2022 Year Built
Osceola County
View All Property Details
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.
MLS # S5126291
Monthly HOA $68
On Site 4 Days
Last Updated 10/19/2026

Location

Contact Agent

Angela Stewart

Angela Stewart

(352) 871-7333

Property Details

Community Information

Address 248 Cheshire Ct, Kissimmee, FL 34758
County Osceola
City Kissimmee
Zip Code 34758
Builder Name JNS Development

Architecture

Bedrooms 4
Bathrooms 2
Year Built 2022
Stories 1
Style Contemporary, Traditional
Construction Materials Block
Construction Status Completed
Flooring Types Ceramic Tile
Roof Shingle
Foundation Slab
Builder Name JNS Development
Garage Spaces 2
Parking Features Garage Door Opener

Features / Amenities

Interior Features Ceiling Fans(s), Living Room/Dining Room Combo, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s)
Appliances Dishwasher, Disposal, Electric Water Heater, Microwave, Range
Flooring Ceramic Tile
Laundry Inside, Laundry Room
Furnished Unfurnished
Additional Rooms Inside Utility
Patio And Porch Covered, Rear Porch
Window Aluminum Frames
Garage Spaces 2
Parking Garage Door Opener
Cooling Central Air
Heating Central, Electric
Air Conditioning Central Air

Property Features

Lot Size 7,710 Sq. Ft. / 0.18 Acres
Lot Features Cleared, In County, Paved
Vegetation Trees/Landscaped
View Trees/Woods
Lot # 13
Flood Zone X
Utilities Cable Available, Electricity Available, Sewer Available, Water Available
Sewer Private Sewer
Water Public
Road Surface Asphalt, Paved
Zoning OPUD
Directions Directions from Orlando Airport (MCO) to 248 Cheshire Ct, Kissimmee, FL 34758:

Take FL-417 S, then exit onto US-17/US-92 S (John Young Pkwy).
Turn right on Pleasant Hill Rd, continue onto Cypress Pkwy.
Turn left on Marigold Ave, then right on Peabody Rd.
Turn left onto Cheshire Ct - home is on the left.
Pets Allowed Breed Restrictions, Number Limit, Yes
Pet Restrictions Must verify restrictions with HOA
Number of Pets 2
Pet Size Large (61-100 Lbs.)

Tax and Financial Info

Tax Year 2024
Tax Annual Amount $4,038
Ownership Fee Simple
Financing Available Cash, Conventional, FHA, VA Loan
Financing Available Cash, Conventional, FHA, VA Loan
Homestead No
Total Annual Fees $810
Average Monthly Fees $67.50
Realtor Info As-Is
Minimum Lease 1-2 Years
Association Fee $90 (paid Annually)
Association Fee Includes Cable TV, Internet, Management
Association Amenities Park, Playground, Vehicle Restrictions
HOA Payment Schedule Annually
HOA / Community Association Required
Monthly Maint. Fee (in addition to HOA fee) $60

Rooms

Size
Primary Bedroom13 X 13
Bedroom 211 X 11
Bedroom 310 X 10
Bedroom 412 X 10
Kitchen12 X 10
Great Room21 X 17

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Schools

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Schedule a Tour

248 Cheshire Ct Kissimmee, FL 34758 | MLS S5126291
ASAP
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Listing provided courtesy of Transcend Realty (407-518-7653).
© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved.
The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional MLS DBA 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; 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 MLS data last updated at October 22, 2026 9:15 AM EST.