View 27 Headlands Road Winchester, NH MLS# 5045812
    Save 27 Headlands Road Winchester, NH MLS# 5045812
    1 of 36
    $725,000
    2

    Beds

    1.1

    Baths

    1,351

    Sq.Ft.

    27 Headlands Road

    Winchester, NH

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    Courtesy of RE/MAX TOWN & COUNTRY
    View 130 Watson Road Winchester, NH MLS# 5071087
      Save 130 Watson Road Winchester, NH MLS# 5071087
      1 of 52
      $694,900
      3

      Beds

      2.0

      Baths

      2,145

      Sq.Ft.

      130 Watson Road

      Winchester, NH

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      Courtesy of COLDWELL BANKER REALTY NASHUA
      View 240 Forest Lake Road Winchester, NH MLS# 5070088
        Save 240 Forest Lake Road Winchester, NH MLS# 5070088
        1 of 34
        $610,000
        4

        Beds

        2.1

        Baths

        2,200

        Sq.Ft.

        240 Forest Lake Road

        Winchester, NH

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        Courtesy of BHG MASIELLO PETERBOROUGH
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 406 Back Ashuelot Road Winchester, NH MLS# 5041951
          Save 406 Back Ashuelot Road Winchester, NH MLS# 5041951
          1 of 39
          $600,000
          7

          Beds

          5.0

          Baths

          5,607

          Sq.Ft.

          406 Back Ashuelot Road

          Winchester, NH

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          Courtesy of BRATTLEBORO AREA REALTY
          View 159 Ashuelot Main Street Winchester, NH MLS# 5072690
          • New Construction with Virtual Tour
          Save 159 Ashuelot Main Street Winchester, NH MLS# 5072690
          1 of 58
          OPEN HOUSE: Sunday 3/22 12:00 PM - 2:00 PM
          $549,900
          4

          Beds

          2.1

          Baths

          2,832

          Sq.Ft.

          159 Ashuelot Main Street

          Winchester, NH

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          Courtesy of LISTWITHFREEDOM.COM
          View 583 Burt Hill Road Winchester, NH MLS# 5074036
            Save 583 Burt Hill Road Winchester, NH MLS# 5074036
            1 of 55
            $549,800
            5

            Beds

            3.0

            Baths

            3,114

            Sq.Ft.

            583 Burt Hill Road

            Winchester, NH

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            Courtesy of HOMESMART SUCCESS REALTY LLC
            View 29 Verry Brook Road Winchester, NH MLS# 5079674
            • Recently Listed
            Save 29 Verry Brook Road Winchester, NH MLS# 5079674
            1 of 24
            OPEN HOUSE: Saturday 3/21 10:00 AM - 12:00 PM
            $450,000
            3

            Beds

            2.0

            Baths

            1,668

            Sq.Ft.

            29 Verry Brook Road

            Winchester, NH

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            Courtesy of KELLER WILLIAMS REALTY METRO-KEENE
            View 11 Ashuelot Street Winchester, NH MLS# 5076139
              Save 11 Ashuelot Street Winchester, NH MLS# 5076139
              1 of 16
              $430,000
              8

              Beds

              3.0

              Baths

              4,226

              Sq.Ft.

              11 Ashuelot Street

              Winchester, NH

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              Courtesy of BHG MASIELLO KEENE
              View 45 Forest Lake Circle Winchester, NH MLS# 5025856
                Save 45 Forest Lake Circle Winchester, NH MLS# 5025856
                1 of 19
                $370,000
                4

                Beds

                2.0

                Baths

                1,500

                Sq.Ft.

                45 Forest Lake Circle

                Winchester, NH

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                Courtesy of RE/MAX TOWN & COUNTRY
                View 94 Main Street Winchester, NH MLS# 5076011
                  Save 94 Main Street Winchester, NH MLS# 5076011
                  1 of 23
                  $370,000
                  4

                  Beds

                  0.0

                  Baths

                  3,240

                  Sq.Ft.

                  94 Main Street

                  Winchester, NH

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                  Courtesy of BHG MASIELLO KEENE
                  View 49 Forest Lake Circle Winchester, NH MLS# 5025747
                    Save 49 Forest Lake Circle Winchester, NH MLS# 5025747
                    1 of 25
                    $350,000
                    2

                    Beds

                    1.0

                    Baths

                    937

                    Sq.Ft.

                    49 Forest Lake Circle

                    Winchester, NH

                    NNEREN
                    Courtesy of RE/MAX TOWN & COUNTRY
                    View 6 Maple Street Winchester, NH MLS# 5076039
                      Save 6 Maple Street Winchester, NH MLS# 5076039
                      1 of 23
                      $339,000
                      Studio

                      Beds

                      0.0

                      Baths

                      2,454

                      Sq.Ft.

                      6 Maple Street

                      Winchester, NH

                      NNEREN
                      Courtesy of BHG MASIELLO KEENE
                      View 292 Richmond Road Winchester, NH MLS# 5077669
                        Save 292 Richmond Road Winchester, NH MLS# 5077669
                        1 of 27
                        $325,000
                        Studio

                        Beds

                        0.0

                        Baths

                        4,739

                        Sq.Ft.

                        292 Richmond Road

                        Winchester, NH

                        NNEREN
                        Courtesy of REALTY ONE GROUP NEXT LEVEL
                        View 10 Swan Street Winchester, NH MLS# 5075238
                          Save 10 Swan Street Winchester, NH MLS# 5075238
                          1 of 40
                          $305,000
                          3

                          Beds

                          1.0

                          Baths

                          1,689

                          Sq.Ft.

                          10 Swan Street

                          Winchester, NH

                          NNEREN
                          Courtesy of ACORN REAL ESTATE GROUP LLC
                          View 21 Kapper Drive Winchester, NH MLS# 5077847
                            Save 21 Kapper Drive Winchester, NH MLS# 5077847
                            1 of 20
                            $299,000
                            3

                            Beds

                            1.0

                            Baths

                            1,056

                            Sq.Ft.

                            21 Kapper Drive

                            Winchester, NH

                            NNEREN
                            Courtesy of LISTWITHFREEDOM.COM
                            View 84 Watson Road Winchester, NH MLS# 5078169
                              Save 84 Watson Road Winchester, NH MLS# 5078169
                              1 of 12
                              $289,000
                              4

                              Beds

                              2.0

                              Baths

                              1,741

                              Sq.Ft.

                              84 Watson Road

                              Winchester, NH

                              NNEREN
                              Courtesy of BHG MASIELLO KEENE
                              View 886 Keene Road Winchester, NH MLS# 5075827
                              • Virtual Tour
                              Save 886 Keene Road Winchester, NH MLS# 5075827
                              1 of 24
                              $259,900
                              2

                              Beds

                              1.0

                              Baths

                              1,424

                              Sq.Ft.

                              886 Keene Road

                              Winchester, NH

                              NNEREN
                              Courtesy of RD LEDOGAR REAL ESTATE
                              View 71 Parker Street Winchester, NH MLS# 5073384
                                Save 71 Parker Street Winchester, NH MLS# 5073384
                                1 of 32
                                $239,000
                                3

                                Beds

                                1.0

                                Baths

                                1,372

                                Sq.Ft.

                                71 Parker Street

                                Winchester, NH

                                NNEREN
                                Courtesy of BHG MASIELLO KEENE
                                View 0 Old Hinsdale Road Winchester, NH MLS# 5052965
                                  Save 0 Old Hinsdale Road Winchester, NH MLS# 5052965
                                  1 of 16
                                  $169,900
                                  Studio

                                  Beds

                                  0.0

                                  Baths

                                  0 Old Hinsdale Road

                                  Winchester, NH

                                  NNEREN
                                  Courtesy of R.H. THACKSTON & COMPANY
                                  View Map3 Lot9-3 Scotland Road Winchester, NH MLS# 4987417
                                    Save Map3 Lot9-3 Scotland Road Winchester, NH MLS# 4987417
                                    1 of 23
                                    $159,000
                                    Studio

                                    Beds

                                    0.0

                                    Baths

                                    Map3 Lot9-3 Scotland Road

                                    Winchester, NH

                                    NNEREN
                                    Courtesy of REALTY ONE GROUP NEXT LEVEL

                                    About Winchester

                                    Listings in Winchester, NH

                                    30

                                    Estimated median home price

                                    $332,000
                                    Winchester NH Homes for Sale & Properties

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

                                    Homes for Sale by Price in Winchester, NH

                                    PriceCount
                                    $0 - 100K2
                                    $100K - 200K6
                                    $200K - 300K5
                                    $300K - 400K6
                                    $400K - 500K2
                                    $500K - 600K3
                                    $600K - 700K2
                                    $700K - 800K1
                                    $800K - 900K1
                                    $900K - 1M0
                                    $1M - Max2

                                    Homes for Sale by Type in Winchester, NH

                                    Property TypeCount
                                    Single Family15
                                    Townhouse0
                                    Condo0
                                    Commercial2
                                    Rental0
                                    Lots and Land7
                                    Condo/Town/CoOp0
                                    CoOp0
                                    Multi Family5
                                    Mobile Home1
                                    Farms0

                                    (Data as of 3/18/2026)

                                    Find Properties in Winchester, NH

                                    Winchester, NH Information

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                                    Information deemed reliable but not guaranteed.

                                    “Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 3/19/2026”

                                    Trends Information provided by ATTOM Data Solutions.