View 95 Colony Drive Winchester, CT MLS# 24150993
    Save 95 Colony Drive Winchester, CT MLS# 24150993
    1 of 1
    OPEN HOUSE: Saturday 2/7 12:00 PM - 2:00 PM
    $285,000
    3

    Beds

    1.1

    Baths

    1,008

    Sq.Ft.

    95 Colony Drive

    Winchester, CT

    View 43 Wallens Street Winchester, CT MLS# 24146596
      Save 43 Wallens Street Winchester, CT MLS# 24146596
      1 of 28
      $275,000
      4

      Beds

      2.0

      Baths

      1,971

      Sq.Ft.

      43 Wallens Street

      Winchester, CT

      View 118 Meadow Street Winchester, CT MLS# 24140514
        Save 118 Meadow Street Winchester, CT MLS# 24140514
        1 of 31
        $269,999
        3

        Beds

        2.0

        Baths

        1,652

        Sq.Ft.

        118 Meadow Street

        Winchester, CT

        The time to sell is now! THE TIME TO SELL IS NOW!
        View 38 Upland Road Winchester, CT MLS# 24131432
          Save 38 Upland Road Winchester, CT MLS# 24131432
          1 of 17
          $269,000
          3

          Beds

          1.1

          Baths

          1,736

          Sq.Ft.

          38 Upland Road

          Winchester, CT

          View 107 Birdsall Street Winchester, CT MLS# 24150688
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          Save 107 Birdsall Street Winchester, CT MLS# 24150688
          1 of 1
          $250,000
          4

          Beds

          2.0

          Baths

          1,874

          Sq.Ft.

          107 Birdsall Street

          Winchester, CT

          View 9 John Street Winchester, CT MLS# 24141326
            Save 9 John Street Winchester, CT MLS# 24141326
            1 of 23
            $230,000
            2

            Beds

            1.1

            Baths

            1,172

            Sq.Ft.

            9 John Street

            Winchester, CT

            View 18 Curtice Street Winchester, CT MLS# 24145729
              Save 18 Curtice Street Winchester, CT MLS# 24145729
              1 of 26
              $229,000
              2

              Beds

              1.1

              Baths

              1,252

              Sq.Ft.

              18 Curtice Street

              Winchester, CT

              View 817 East Wakefield Boulevard Winchester, CT MLS# 24143747
                Save 817 East Wakefield Boulevard Winchester, CT MLS# 24143747
                1 of 32
                $225,000
                2

                Beds

                1.0

                Baths

                1,051

                Sq.Ft.

                817 East Wakefield Boulevard

                Winchester, CT

                About Winchester

                Often called the “Gateway to the Berkshire Mountains,” Winchester blends the natural beauty of lakes and freshwater springs with more than 650 flourishing businesses.  The result is a strong local economy within a relaxed small-town lifestyle.  Winsted is the downtown district of Winchester, home to the campus for Northwestern Connecticut Community Technical College.  The town is noted for its magnificent ecclesiastical architecture and for one of the state’s largest lakes.

                Listings in Winchester, CT

                60

                Estimated median home price

                $307,500
                Winchester CT Homes for Sale & Properties

                Weichert Realtors is one of the nation's leading providers of Winchester, Connecticut real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, CT.

                Homes for Sale by Price in Winchester, CT

                PriceCount
                $0 - 100K10
                $100K - 200K5
                $200K - 300K15
                $300K - 400K13
                $400K - 500K5
                $500K - 600K1
                $600K - 700K2
                $700K - 800K5
                $800K - 900K2
                $900K - 1M1
                $1M - Max1

                Homes for Sale by Type in Winchester, CT

                Property TypeCount
                Single Family24
                Townhouse0
                Condo2
                Commercial10
                Rental13
                Lots and Land16
                Condo/Town/CoOp0
                CoOp0
                Multi Family8
                Mobile Home0
                Farms0

                (Data as of 1/31/2026)

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