View 605 East Wakefield Boulevard Winchester, CT MLS# 24139172
    Save 605 East Wakefield Boulevard Winchester, CT MLS# 24139172
    1 of 6
    $12,500
    Studio

    Beds

    0.0

    Baths

    605 East Wakefield Boulevard

    Winchester, CT

    View 52 White Street Winchester, CT MLS# 24132699
      Save 52 White Street Winchester, CT MLS# 24132699
      $29,000
      Studio

      Beds

      0.0

      Baths

      52 White Street

      Winchester, CT

      View 124 Rockwell Street Winchester, CT MLS# 24073710
        Save 124 Rockwell Street Winchester, CT MLS# 24073710
        1 of 2
        $29,000
        Studio

        Beds

        0.0

        Baths

        124 Rockwell Street

        Winchester, CT

        The time to sell is now! THE TIME TO SELL IS NOW!
        View 48 Bridge Street Winchester, CT MLS# 24073721
          Save 48 Bridge Street Winchester, CT MLS# 24073721
          1 of 1
          $23,900
          Studio

          Beds

          0.0

          Baths

          48 Bridge Street

          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

          74

          Estimated median home price

          $314,900
          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 - 100K11
          $100K - 200K9
          $200K - 300K16
          $300K - 400K14
          $400K - 500K6
          $500K - 600K2
          $600K - 700K1
          $700K - 800K5
          $800K - 900K4
          $900K - 1M2
          $1M - Max4

          Homes for Sale by Type in Winchester, CT

          Property TypeCount
          Single Family31
          Townhouse0
          Condo5
          Commercial9
          Rental15
          Lots and Land18
          Condo/Town/CoOp0
          CoOp0
          Multi Family11
          Mobile Home0
          Farms0

          (Data as of 11/11/2025)

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