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Under contract
  • $339,900

    50 Overlook Road, Winchester, CT 06098

    3beds
    1,488sqft
    : 
    $2,412/mo
    Get pre-qualified
    Single Family Residence
    Built in 1949
    0.97 Acres Lot
    $-- Zestimate®
    $228/sqft
    $-- HOA

    What's special

    Thermopane windowsThree heating sourcesAdditional detached garageThree comfortable bedroomsAmple closet spaceLarge kitchenDining room
    Lovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial offers approximately 1,500 sq. ft. of living space on a 1-acre lot on the outskirts of town, yet within walking distance to the beach at Highland Lake. The main level features a spacious living room, large kitchen, dining room, full bath and inviting 3-season porch. Upstairs are three comfortable bedrooms with ample closet space. Hardwood floors run throughout the home, adding to its classic charm. Energy-conscious features include three heating sources: an oil-fired boiler, pellet stove in the living room and a magnificent soapstone wood stove in the lower level. The home also offers plenty of insulation, thermopane windows and a roof installed in 2021. Outside, you'll find excellent garage and storage space, including a large barn/garage with room for vehicles and a workshop, plus an additional detached garage. Set on nearly an acre with convenient access to Highland Lake and town amenities, this well-cared-for home is ready for its next chapter. This one is worth seeing!
    34 days
    279
    6

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    David Sartirana (860)806-0225,

    Northwest CT Realty 860-379-7245,

    Amy Sartirana 860-605-6217,

    Northwest CT Realty

    Source: Smart MLS,MLS#: 24210012MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 1
      • Full bathrooms: 1
      Primary bedroom
      • Level: Upper
      • Area: 247 Square Feet
      • Dimensions: 13 x 19
      Bedroom
      • Level: Upper
      • Area: 156 Square Feet
      • Dimensions: 12 x 13
      Bedroom
      • Level: Upper
      • Area: 156 Square Feet
      • Dimensions: 12 x 13
      Dining room
      • Level: Main
      • Area: 121 Square Feet
      • Dimensions: 11 x 11
      Kitchen
      • Level: Main
      • Area: 221 Square Feet
      • Dimensions: 13 x 17
      Living room
      • Features: Pellet Stove, Hardwood Floor
      • Level: Main
      • Area: 180 Square Feet
      • Dimensions: 12 x 15
      Sun room
      • Level: Main
      • Area: 140 Square Feet
      • Dimensions: 7 x 20
      Heating
      • Hot Water, Oil
      Cooling
      • None
      Appliances
      • Included: Oven/Range, Refrigerator, Washer, Dryer, Water Heater
      • Laundry: Lower Level
      Features
      • Windows: Thermopane Windows
      • Basement: Full,Concrete
      • Attic: Storage,Access Via Hatch
      • Has fireplace: No
      Interior area
      • Total structure area: 1,488
      • Total interior livable area: 1,488 sqft
      • Finished area above ground: 1,488

      Property

      Parking
      • Total spaces: 8
      • Parking features: Barn, Detached, Off Street
      • Garage spaces: 3
      Features
      • Patio & porch: Porch
      Lot
      • Size: 0.97 Acres
      • Features: Corner Lot, Few Trees, Level
      Details
      • Parcel number: 924483
      • Zoning: TSF
      • Other equipment: Generator Ready

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Block, Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1949

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available
      Green energy
      • Energy efficient items: Windows

      Community & HOA

      Community
      • Features: Golf, Lake, Library, Medical Facilities, Park, Near Public Transport
      • Subdivision: Winsted
      HOA
      • Has HOA: No
      Location
      • Region: Winsted

      Financial & listing details

      • Price per square foot: $228/sqft
      • Tax assessed value: $142,800
      • Annual tax amount: $4,284
      • Date on market: 9/26/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        10/30/2026Pending sale$339,900$228/sqft
        Source: Smart MLS #24210012 Report a problem
        9/26/2026Listed for sale$339,900$228/sqft
        Source: Smart MLS #24210012 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,165 +10.5%$142,800
        2024$3,768 $142,800
        2023$3,768 +5.7%$142,800 +34.3%
        2022$3,566 $106,330
        2021$3,566 $106,330
        2020$3,566 $106,330
        2019$3,566 $106,330
        2018$3,566 +5%$106,330 +5%
        2017$3,397 $101,290
        2016$3,397 +2.6%$101,290
        2015$3,312 +2.5%$101,290
        2014$3,232 +2.3%$101,290
        2013$3,160 -3%$101,290 -20.9%
        2012$3,258 $128,100
        2011$3,258 $128,100
        2010$3,258 +3.1%$128,100
        2009$3,160 $128,100
        2008$3,160 +3%$128,100 +43.1%
        2007$3,068 +2.8%$89,530
        2006$2,985 +1.1%$89,530
        2005$2,953 +9.5%$89,530
        2003$2,697 +0.9%$89,530 -7.7%
        1995$2,674 $97,040
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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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: 06098

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: Gilbert

        Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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