View 27 Headlands Road Winchester, NH MLS# 5045812
    Save 27 Headlands Road Winchester, NH MLS# 5045812
    1 of 36
    $715,000
    2

    Beds

    1.1

    Baths

    1,351

    Sq.Ft.

    27 Headlands Road

    Winchester, NH

    NNEREN
    Courtesy of RE/MAX TOWN & COUNTRY
    View 39 Headlands Road Winchester, NH MLS# 5087379
      Save 39 Headlands Road Winchester, NH MLS# 5087379
      1 of 33
      $698,000
      3

      Beds

      2.0

      Baths

      1,364

      Sq.Ft.

      39 Headlands Road

      Winchester, NH

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      Courtesy of BHG MASIELLO KEENE
      View 295 Manning Hill Road Winchester, NH MLS# 5089279
        Save 295 Manning Hill Road Winchester, NH MLS# 5089279
        1 of 55
        $650,000
        3

        Beds

        2.0

        Baths

        2,671

        Sq.Ft.

        295 Manning Hill Road

        Winchester, NH

        NNEREN
        Courtesy of BHG MASIELLO KEENE
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 581 Keene Road Winchester, NH MLS# 5094418
          Save 581 Keene Road Winchester, NH MLS# 5094418
          1 of 7
          $629,000
          5,567

          Sq.Ft.

          581 Keene Road

          Winchester, NH

          NNEREN
          Courtesy of H. G. JOHNSON REAL ESTATE
          View 484 Scofield Mountain Road Winchester, NH MLS# 5101558
          • Recently Listed
          Save 484 Scofield Mountain Road Winchester, NH MLS# 5101558
          1 of 52
          $599,000
          3

          Beds

          2.0

          Baths

          2,516

          Sq.Ft.

          484 Scofield Mountain Road

          Winchester, NH

          NNEREN
          Courtesy of R.H. THACKSTON & COMPANY
          View 15 High Street Winchester, NH MLS# 5085975
            Save 15 High Street Winchester, NH MLS# 5085975
            1 of 15
            $550,000
            10

            Beds

            8.0

            Baths

            4,519

            Sq.Ft.

            15 High Street

            Winchester, NH

            NNEREN
            Courtesy of HORVATH & TREMBLAY LLC
            View 418 Forest Lake Road Winchester, NH MLS# 5101659
              Save 418 Forest Lake Road Winchester, NH MLS# 5101659
              1 of 42
              $499,900
              2

              Beds

              1.1

              Baths

              1,392

              Sq.Ft.

              418 Forest Lake Road

              Winchester, NH

              NNEREN
              Courtesy of RE/MAX TOWN & COUNTRY
              View 166 Keene Road Winchester, NH MLS# 5092617
                Save 166 Keene Road Winchester, NH MLS# 5092617
                1 of 60
                $479,900
                3

                Beds

                1.1

                Baths

                1,808

                Sq.Ft.

                166 Keene Road

                Winchester, NH

                NNEREN
                Courtesy of BHG MASIELLO KEENE
                View 305 Richmond Road Winchester, NH MLS# 5093431
                  Save 305 Richmond Road Winchester, NH MLS# 5093431
                  1 of 54
                  $475,000
                  5

                  Beds

                  4.0

                  Baths

                  2,790

                  Sq.Ft.

                  305 Richmond Road

                  Winchester, NH

                  NNEREN
                  Courtesy of COLDWELL BANKER REALTY NASHUA
                  View 71 Headlands Road Winchester, NH MLS# 5096976
                    Save 71 Headlands Road Winchester, NH MLS# 5096976
                    1 of 42
                    $445,000
                    3

                    Beds

                    2.0

                    Baths

                    1,066

                    Sq.Ft.

                    71 Headlands Road

                    Winchester, NH

                    NNEREN
                    Courtesy of HKS ASSOCIATES, INC.
                    View 152 Old Chesterfield Road Winchester, NH MLS# 5093714
                      Save 152 Old Chesterfield Road Winchester, NH MLS# 5093714
                      1 of 31
                      $425,000
                      1

                      Beds

                      2.0

                      Baths

                      1,232

                      Sq.Ft.

                      152 Old Chesterfield Road

                      Winchester, NH

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                      Courtesy of BHG MASIELLO KEENE
                      View 253 Back Ashuelot Road Winchester, NH MLS# 5095024
                      • Virtual Tour
                      Save 253 Back Ashuelot Road Winchester, NH MLS# 5095024
                      1 of 53
                      $425,000
                      1

                      Beds

                      1.0

                      Baths

                      1,290

                      Sq.Ft.

                      253 Back Ashuelot Road

                      Winchester, NH

                      NNEREN
                      Courtesy of BHG MASIELLO KEENE
                      View 000 Burt Hill Road Winchester, NH MLS# 5100318
                      • Recently Listed
                      Save 000 Burt Hill Road Winchester, NH MLS# 5100318
                      1 of 32
                      $400,000
                      Studio

                      Beds

                      0.0

                      Baths

                      000 Burt Hill Road

                      Winchester, NH

                      NNEREN
                      Courtesy of MONADNOCK REALTY GROUP LLC
                      View 55 Verry Brook Road Winchester, NH MLS# 5100355
                        Save 55 Verry Brook Road Winchester, NH MLS# 5100355
                        1 of 37
                        $359,500
                        3

                        Beds

                        1.1

                        Baths

                        1,192

                        Sq.Ft.

                        55 Verry Brook Road

                        Winchester, NH

                        NNEREN
                        Courtesy of BHG MASIELLO KEENE
                        View 229 Back Ashuelot Road Winchester, NH MLS# 5098523
                          Save 229 Back Ashuelot Road Winchester, NH MLS# 5098523
                          1 of 60
                          $324,900
                          2

                          Beds

                          1.0

                          Baths

                          960

                          Sq.Ft.

                          229 Back Ashuelot Road

                          Winchester, NH

                          NNEREN
                          Courtesy of LPT REALTY
                          View 292 Richmond Road Winchester, NH MLS# 5077669
                            Save 292 Richmond Road Winchester, NH MLS# 5077669
                            1 of 25
                            $290,000
                            Studio

                            Beds

                            0.0

                            Baths

                            4,739

                            Sq.Ft.

                            292 Richmond Road

                            Winchester, NH

                            NNEREN
                            Courtesy of REALTY ONE GROUP NEXT LEVEL
                            View 19 Back Ashuelot Road Winchester, NH MLS# 5086470
                              Save 19 Back Ashuelot Road Winchester, NH MLS# 5086470
                              1 of 26
                              $285,000
                              4

                              Beds

                              2.0

                              Baths

                              1,493

                              Sq.Ft.

                              19 Back Ashuelot Road

                              Winchester, NH

                              NNEREN
                              Courtesy of EXP REALTY
                              View 65 Mechanic Street Winchester, NH MLS# 5094140
                                Save 65 Mechanic Street Winchester, NH MLS# 5094140
                                1 of 19
                                $259,900
                                4

                                Beds

                                2.0

                                Baths

                                2,128

                                Sq.Ft.

                                65 Mechanic Street

                                Winchester, NH

                                NNEREN
                                Courtesy of BHG MASIELLO KEENE
                                View 65 Mechanic Street Winchester, NH MLS# 5101665
                                • Recently Listed
                                Save 65 Mechanic Street Winchester, NH MLS# 5101665
                                1 of 20
                                $259,900
                                3

                                Beds

                                2.0

                                Baths

                                2,128

                                Sq.Ft.

                                65 Mechanic Street

                                Winchester, NH

                                NNEREN
                                Courtesy of BHG MASIELLO KEENE
                                View 369 Manning Hill Road Winchester, NH MLS# 5096726
                                  Save 369 Manning Hill Road Winchester, NH MLS# 5096726
                                  1 of 20
                                  $190,000
                                  2

                                  Beds

                                  1.0

                                  Baths

                                  894

                                  Sq.Ft.

                                  369 Manning Hill Road

                                  Winchester, NH

                                  NNEREN
                                  Courtesy of R.H. THACKSTON & COMPANY

                                  About Winchester

                                  Listings in Winchester, NH

                                  38

                                  Estimated median home price

                                  $287,500
                                  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 - 100K7
                                  $100K - 200K9
                                  $200K - 300K4
                                  $300K - 400K3
                                  $400K - 500K6
                                  $500K - 600K2
                                  $600K - 700K3
                                  $700K - 800K1
                                  $800K - 900K0
                                  $900K - 1M0
                                  $1M - Max3

                                  Homes for Sale by Type in Winchester, NH

                                  Property TypeCount
                                  Single Family14
                                  Townhouse0
                                  Condo0
                                  Commercial3
                                  Rental1
                                  Lots and Land14
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family4
                                  Mobile Home3
                                  Farms0

                                  (Data as of 8/1/2026)

                                  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 8/6/2026”

                                  Trends Information provided by ATTOM Data Solutions.