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

    NNEREN
    Courtesy of BHG MASIELLO KEENE
    View 60 Forest Lake Road Winchester, NH MLS# 5106346
    • Recently Listed
    Save 60 Forest Lake Road Winchester, NH MLS# 5106346
    1 of 51
    OPEN HOUSE: Saturday 8/29 10:00 AM - 12:00 PM
    $650,000
    2

    Beds

    2.0

    Baths

    1,676

    Sq.Ft.

    60 Forest Lake Road

    Winchester, NH

    NNEREN
    Courtesy of KELLER WILLIAMS REALTY METRO-KEENE
    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
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 295 Manning Hill Road Winchester, NH MLS# 5089279
        Save 295 Manning Hill Road Winchester, NH MLS# 5089279
        1 of 59
        $599,900
        3

        Beds

        2.0

        Baths

        2,671

        Sq.Ft.

        295 Manning Hill Road

        Winchester, NH

        NNEREN
        Courtesy of BHG MASIELLO KEENE
        View 484 Scofield Mountain Road Winchester, NH MLS# 5101558
          Save 484 Scofield Mountain Road Winchester, NH MLS# 5101558
          1 of 52
          OPEN HOUSE: Sunday 8/30 10:30 AM - 1:00 PM
          $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 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 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
                    Save 000 Burt Hill Road Winchester, NH MLS# 5100318
                    1 of 32
                    $380,000
                    Studio

                    Beds

                    0.0

                    Baths

                    000 Burt Hill Road

                    Winchester, NH

                    NNEREN
                    Courtesy of MONADNOCK REALTY GROUP LLC
                    View 10 Burt Hill Road Winchester, NH MLS# 5105670
                    • Recently Listed with Virtual Tour
                    Save 10 Burt Hill Road Winchester, NH MLS# 5105670
                    1 of 39
                    $369,900
                    3

                    Beds

                    2.0

                    Baths

                    1,956

                    Sq.Ft.

                    10 Burt Hill Road

                    Winchester, NH

                    NNEREN
                    Courtesy of BHG MASIELLO PETERBOROUGH
                    View 88 Back Ashuelot Road Winchester, NH MLS# 5105078
                    • Recently Listed with Virtual Tour
                    Save 88 Back Ashuelot Road Winchester, NH MLS# 5105078
                    1 of 35
                    $349,900
                    3

                    Beds

                    1.1

                    Baths

                    1,944

                    Sq.Ft.

                    88 Back Ashuelot Road

                    Winchester, NH

                    NNEREN
                    Courtesy of REDFIN CORPORATION
                    View 73 Ashuelot Main Street Winchester, NH MLS# 5107206
                    • Recently Listed
                    Save 73 Ashuelot Main Street Winchester, NH MLS# 5107206
                    1 of 17
                    $325,000
                    3

                    Beds

                    1.0

                    Baths

                    1,548

                    Sq.Ft.

                    73 Ashuelot Main Street

                    Winchester, NH

                    NNEREN
                    Courtesy of ACORN REAL ESTATE GROUP LLC
                    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 12 Rabbit Hollow Road Winchester, NH MLS# 5105294
                          Save 12 Rabbit Hollow Road Winchester, NH MLS# 5105294
                          1 of 21
                          $289,900
                          3

                          Beds

                          1.0

                          Baths

                          1,118

                          Sq.Ft.

                          12 Rabbit Hollow Road

                          Winchester, NH

                          NNEREN
                          Courtesy of RE/MAX SYNERGY
                          View 65 Mechanic Street Winchester, NH MLS# 5101665
                            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 65 Mechanic Street Winchester, NH MLS# 5094140
                              Save 65 Mechanic Street Winchester, NH MLS# 5094140
                              1 of 19
                              $239,900
                              4

                              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
                                $150,000
                                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

                                37

                                Estimated median home price

                                $324,900
                                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 - 100K6
                                $100K - 200K8
                                $200K - 300K4
                                $300K - 400K5
                                $400K - 500K5
                                $500K - 600K2
                                $600K - 700K3
                                $700K - 800K1
                                $800K - 900K0
                                $900K - 1M0
                                $1M - Max3

                                Homes for Sale by Type in Winchester, NH

                                Property TypeCount
                                Single Family18
                                Townhouse0
                                Condo0
                                Commercial3
                                Rental1
                                Lots and Land12
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family3
                                Mobile Home1
                                Farms0

                                (Data as of 8/29/2026)

                                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 8/29/2026”

                                Trends Information provided by ATTOM Data Solutions.