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For sale
    • $499,000

    88 Winthrop Road, Chester, CT 06412

    3beds
    2,240sqft
    : 
    $3,543/mo
    Get pre-qualified
    Single Family Residence
    Built in 1980
    33.97 Acres Lot
    $-- Zestimate®
    $223/sqft
    $-- HOA

    What's special

    Unique contemporary homeSoaring cathedral ceilingsExposed beamsDedicated garage bayVersatile outbuildingsDirectly abutting state forestOpen-concept interior
    Set on nearly 34 acres and directly abutting state forest, this unique contemporary home offers privacy, space, and endless potential. The open-concept interior features soaring cathedral ceilings and exposed beams, creating a dramatic and inviting living space. The home offers 3 bedrooms, 2.5 bathrooms, and an oversized 2-car attached garage. A separate approximately 800-square-foot barn/shop provides additional workspace, storage, or hobby potential and includes a dedicated garage bay. This home is an excellent opportunity for a buyer looking to restore and customize the property to their vision. With substantial acreage, direct access to nature, and versatile outbuildings, this property presents a rare opportunity to create a private estate, homestead, or retreat.
    2 hours
    318
    34

    Zillow last checked:

    Listing updated:

    Listed by:

    Carlos Ortiz (860)908-7809,

    RE/MAX Heritage 203-646-2380,

    Timothy Sylvestre 860-377-0461,

    RE/MAX Heritage

    Source: Smart MLS,MLS#: 24204497MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Heating
      • Forced Air, Oil
      Cooling
      • Window Unit(s)
      Appliances
      • Included: None, Water Heater
      Features
      • Basement: Crawl Space
      • Attic: Access Via Hatch
      • Has fireplace: No
      Interior area
      • Total structure area: 2,240
      • Total interior livable area: 2,240 sqft
      • Finished area above ground: 2,240

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached
      • Attached garage spaces: 2
      Features
      • Exterior features: Balcony
      Lot
      • Size: 33.97 Acres
      • Features: Secluded, Wooded
      Details
      • Additional structures: Shed(s)
      • Parcel number: 941053
      • Zoning: R-2

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Vertical Siding, Wood Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1980

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Subdivision: Cedar Lake
      HOA
      • Has HOA: No
      Location
      • Region: Chester

      Financial & listing details

      • Price per square foot: $223/sqft
      • Tax assessed value: $302,750
      • Annual tax amount: $8,198
      • Date on market: 9/10/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        9/10/2026Listed for sale$499,000-23.2%$223/sqft
        Source: Smart MLS #24204497 Report a problem
        9/3/2026Listing removed$650,000$290/sqft
        Source: Smart MLS #24179377 Report a problem
        8/15/2026Price change$650,000-18.7%$290/sqft
        Source: Smart MLS #24179377 Report a problem
        7/13/2026Listed for sale$799,900-18.8%$357/sqft
        Source: Smart MLS #24179377 Report a problem
        12/2/2025Listing removed$985,000$440/sqft
        Source: Smart MLS #24081148 Report a problem
        4/1/2025Listed for sale$985,000+15.9%$440/sqft
        Source: Smart MLS #24081148 Report a problem
        3/24/2021Listing removed--
        Source: Owner Report a problem
        11/11/2018Listing removed$850,000$379/sqft
        Source: Owner Report a problem
        8/13/2018Listed for sale$850,000+30.8%$379/sqft
        Source: Owner Report a problem
        7/23/2013Listing removed$650,000$290/sqft
        Source: CENTURY 21 Scala Group #99018434 Report a problem
        3/2/2013Listed for sale$650,000-31.5%$290/sqft
        Source: CENTURY 21 Access America #99018434 Report a problem
        5/25/2011Listing removed$949,000$424/sqft
        Source: THIMBLE ISLAND REALTY LLC #M9114411 Report a problem
        2/26/2011Listed for sale$949,000$424/sqft
        Source: THIMBLE ISLAND REALTY LLC #M9114411 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$8,198 +10.8%$302,750
        2024$7,402 +6.7%$302,750 +29.7%
        2023$6,935 +0.7%$233,490
        2022$6,888 $233,490
        2021$6,888 +3.1%$233,490
        2020$6,682 -0.6%$233,490
        2019$6,722 -5.3%$233,490 -10.8%
        2018$7,096 +2.8%$261,760
        2017$6,900 +4.1%$261,760
        2015$6,628 +2%$261,760
        2014$6,497 +2.7%$261,760 -9.2%
        2013$6,326 -2.3%$288,190
        2012$6,476 +1.6%$288,190
        2011$6,372 $288,190
        2010$6,372 +4.7%$288,190
        2009$6,084 +16.5%$288,190 +23.4%
        2006$5,223 +38.5%$233,500 +53.8%
        2001$3,770 -17.4%$151,850 -35.6%
        1995$4,566 $235,970
        Find assessor info on the county website

        Monthly payment

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        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.
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        Climate risks

        Neighborhood: 06412

        Getting around

        0 / 100
        Car-Dependent
        29 / 100
        Somewhat Bikeable

        Nearby schools

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