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For sale
    • Price cut: $5K (7/22)
    $299,500

    248 CHESHIRE COURT, KISSIMMEE, FL 34758

    4beds
    1,695sqft
    : 
    $2,040/mo
    Get pre-qualified
    Single Family Residence
    Built in 2022
    7,710 Square Feet Lot
    $295,800 Zestimate®
    $177/sqft
    $68/mo HOA

    What's special

    Large backyardGenerous master suiteQuiet cul-de-sacPeaceful cul-de-sacIdeal for outdoor relaxationPlenty of natural lightSpacious open layout
    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.
    365 days
    |
    162
    |
    10
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Jacob Hara 407-933-5478,

    TRANSCEND REALTY 407-518-7653

    Source: Stellar MLS,MLS#: S5126291MLS LogoOriginating MLS: Osceola

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Utility Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 169 Square Feet
      • Dimensions: 13x13
      Bedroom 2
      • Features: Built-in Closet
      • Level: First
      • Area: 121 Square Feet
      • Dimensions: 11x11
      Bedroom 3
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 100 Square Feet
      • Dimensions: 10x10
      Bedroom 4
      • Features: Built-in Closet
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 12x10
      Great room
      • Level: First
      • Area: 357 Square Feet
      • Dimensions: 21x17
      Kitchen
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 12x10
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Electric Water Heater, Microwave, Range
      • Laundry: Inside, Laundry Room
      Features
      • Ceiling Fan(s), Living Room/Dining Room Combo, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s)
      • Flooring: Ceramic Tile
      • Doors: Sliding Doors
      • Has fireplace: No
      Interior area
      • Total structure area: 2,111
      • Total interior livable area: 1,695 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Rear Porch
      • Has view: Yes
      • View description: Trees/Woods
      Lot
      • Size: 7,710 Square Feet
      • Features: Cleared, In County
      • Residential vegetation: Trees/Landscaped
      Details
      • Parcel number: 252628610006370130
      • Zoning: OPUD
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary,Traditional
      • Property subtype: Single Family Residence
      Materials
      • Block
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • Completed
      • New construction: No
      • Year built: 2022
      Details
      • Builder name: JNS Development

      Utilities & green energy

      • Sewer: Private Sewer
      • Water: Public
      • Utilities for property: Cable Available, Electricity Available, Sewer Available, Water Available

      Community & HOA

      Community
      • Features: Deed Restrictions, Park, Playground
      • Pet fee: $0 monthly
      • Subdivision: POINCIANA VILLAGE 02 NEIGHBORHOOD 01
      HOA
      • Has HOA: Yes
      • Amenities included: Park, Playground, Vehicle Restrictions
      • Services included: Cable TV, Internet, Manager
      • HOA fee: $68 monthly
      • HOA name: Mark Maldonado Serrano
      • HOA phone: 863-424-0900
      Location
      • Region: Kissimmee

      Financial & listing details

      • Price per square foot: $177/sqft
      • Tax assessed value: $267,500
      • Annual tax amount: $4,038
      • Date on market: 5/5/2025
      • Cumulative days on market: 333 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        $295,800

        $281,000 - $311,000

        $2,095/mo

        Price history

        DateEventPrice
        7/22/2026Price change$299,500-1.6%$177/sqft
        Source: Stellar MLS #S5126291 Report a problem
        5/26/2026Listed for sale$304,500$180/sqft
        Source: Stellar MLS #S5126291 Report a problem
        5/13/2026Pending sale$304,500$180/sqft
        Source: Stellar MLS #S5126291 Report a problem
        5/4/2026Price change$304,500-1%$180/sqft
        Source: Stellar MLS #S5126291 Report a problem
        4/15/2026Price change$307,500-0.8%$181/sqft
        Source: Stellar MLS #S5126291 Report a problem
        2/11/2026Listed for sale$309,950$183/sqft
        Source: Stellar MLS #S5126291 Report a problem
        12/31/2025Pending sale$309,950$183/sqft
        Source: Stellar MLS #S5126291 Report a problem
        10/22/2025Price change$309,950-1.6%$183/sqft
        Source: Stellar MLS #S5126291 Report a problem
        7/30/2025Listed for sale$314,950-4.5%$186/sqft
        Source: Stellar MLS #S5126291 Report a problem
        5/27/2025Listing removed$329,950$195/sqft
        Source: Stellar MLS #S5126291 Report a problem
        5/5/2025Listed for sale$329,950-1.5%$195/sqft
        Source: Stellar MLS #S5126291 Report a problem
        5/2/2024Listing removed--
        Source: Zillow Rentals Report a problem
        4/30/2024Listed for rent$2,195+2.1%$1/sqft
        Source: Zillow Rentals Report a problem
        4/10/2023Listing removed--
        Source: Zillow Rentals Report a problem
        3/15/2023Price change$2,150-2.3%$1/sqft
        Source: Zillow Rentals Report a problem
        2/18/2023Listed for rent$2,200$1/sqft
        Source: Zillow Rentals Report a problem
        2/16/2023Listing removed--
        Source: Stellar MLS #S5069483 Report a problem
        1/30/2023Price change$334,850-3.9%$198/sqft
        Source: Stellar MLS #S5069483 Report a problem
        10/7/2022Price change$348,500-3.2%$206/sqft
        Source: Stellar MLS #S5069483 Report a problem
        9/8/2022Listed for sale$359,850$212/sqft
        Source: Stellar MLS #S5069483 Report a problem
        8/9/2022Pending sale$359,850$212/sqft
        Source: Stellar MLS #S5069483 Report a problem
        7/19/2022Price change$359,850-1.4%$212/sqft
        Source: Stellar MLS #S5069483 Report a problem
        6/17/2022Listed for sale$364,895+710.9%$215/sqft
        Source: Stellar MLS #S5069483 Report a problem
        7/1/2021Sold$45,000$27/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,419 +9.4%$267,500 +8.4%
        2024$4,038 -0.6%$246,800 +0.2%
        2023$4,061 +685.2%$246,300 +565.7%
        2022$517 +91.4%$37,000 +69.7%
        2021$270 +3.8%$21,800
        2020$260 +10.2%$21,800 +14.7%
        2019$236 $19,000 +33.8%
        2018$236 +19.2%$14,200 +24.6%
        2017$198 +13.4%$11,400 -14.3%
        2016$175 -12.6%$13,300
        2015$200 -3.8%$13,300 -16.9%
        2014$208 $16,000 +40.4%
        2013-- $11,400 +32.6%
        2012-- $8,600
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34758

        Getting around

        0 / 100
        Car-Dependent
        13 / 100
        Minimal Transit
        26 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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