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$309,950 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,695 Sq. Ft.
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One or more photo(s) has been 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.

Full Property Details for 248 Cheshire Ct

General

  • Price: $309,950
  • HOA FEE: $8/month
  • HOA FEE FREQ.: Annually
  • Taxes: $4,038 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5126291
  • Updated: 12/31/2025
  • Added to Site: 258 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 6
  • Interior Features: Ceiling Fan(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
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Park, Playground, Vehicle Restrictions

Exterior

  • Exterior Features: Sliding Doors
  • Deck/Patio: Covered, Rear Porch
  • Porch/Patio/Deck: Covered, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Garage Door Opener

Location

  • Area: 34758 - Kissimmee / Poinciana
  • County: Osceola
  • Development Name: 34758 - Kissimmee / Poinciana
  • Subdivision: POINCIANA VILLAGE 02 NEIGHBORHOOD 01
  • Driving 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.
  • Direction Faces: Northwest

Community

  • Community Name: 34758 - Kissimmee / Poinciana
  • Community Features: Deed Restrictions, Park, Playground
  • Optional Amenities: Park, Playground, Vehicle Restrictions
  • Association: Yes
  • Assoc. Name: Mark Maldonado Serrano
  • Assoc. Fees Include: Cable TV, Internet, Manager
  • Number of Pets: 2
  • Pet Restrictions: Must verify restrictions with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Private Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Available, Sewer Available, Water Available

Structural Information

  • Architectural Info: Contemporary, Traditional
  • Architectural Style: Contemporary, Traditional
  • Builder: JNS Development
  • Exterior Const.: Block
  • Roof: Shingle
  • Windows: Aluminum Frames
  • Stories/Levels: One
  • Square Feet: 1,695
  • Sq. Ft. Source: Builder
  • Year Built: 2022

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 7,710
  • Lot Size: 7710
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Association Fee: $90
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,038
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: POINCIANA V 2 NBD 1 PB 3 PG 69 BLK 637 LOT 13 27/26/28
  • Flood Zone Info: x
  • APN: 252628610006370130
  • Property ID: 252628610006370130
  • Block/Lot/Section: 637

Listed by Transcend Realty

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Listing agent

— 248 Cheshire Ct —

  • Transcend Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 248 Cheshire Ct

School District:Osceola County School District
NameGradesDistance
Deerwood Elementary School, Kissimmee, FL
3701 Marigold Avenue, Kissimmee, FL 34758
PK-50.8 mi
Discovery Intermediate School
5350 San Miguel Road, Kissimmee, FL 34758
6-81.4 mi
Poinciana High School
2300 South Poinciana Boulevard, Kissimmee, FL 34758
9-123.1 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 248 Cheshire Ct Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/22/2025
Price Reduced
$309,950
-1.59%
MLS
7/30/2025
Price Reduced
$314,950
-4.55%
MLS
5/05/2025
Listed
$329,950
633.22%
MLS
6/29/2021
Sold
$45,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 248 Cheshire Ct

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,419
9%
$267,500
8%
2024
$4,038
-1%
$246,800
—
2023
$4,061
685%
$246,300
566%
2022
$517
91%
$37,000
70%
2021
$270
36%
$21,800
54%
2018
$198
13%
$14,200
25%
2017
$175
-12%
$11,400
-14%
2016
$200
-15%
$13,300
-4%
2019
$236
20%
$13,794
4%
2015
$196
-6%
$13,300
-17%
2014
$208
24%
$16,000
40%
2013
$168
—
$11,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Transcend Realty

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248 Cheshire Court, Kissimmee, FL 34758 (MLS# S5126291) is a Single Family property with 4 bedrooms and 2 full bathrooms. 248 Cheshire Court is currently listed for $309,950 and was received on May 05, 2025. Want to learn more about 248 Cheshire Court? Do you have questions about finding other Single Family real estate for sale in Kissimmee? You can browse all Kissimmee real estate or contact a Coldwell Banker agent to request more information.

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