View 71 Headlands Road Winchester, NH MLS# 5096976
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Save 71 Headlands Road Winchester, NH MLS# 5096976
1 of 42
$495,000
3

Beds

2.0

Baths

1,066

Sq.Ft.

71 Headlands Road

Winchester, NH

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Courtesy of HKS ASSOCIATES, INC.
View 369 Manning Hill Road Winchester, NH MLS# 5096726
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Save 369 Manning Hill Road Winchester, NH MLS# 5096726
1 of 20
$200,000
2

Beds

1.0

Baths

894

Sq.Ft.

369 Manning Hill Road

Winchester, NH

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Courtesy of R.H. THACKSTON & COMPANY
View 253 Back Ashuelot Road Winchester, NH MLS# 5095024
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Save 253 Back Ashuelot Road Winchester, NH MLS# 5095024
1 of 30
$425,000
1

Beds

1.0

Baths

1,290

Sq.Ft.

253 Back Ashuelot Road

Winchester, NH

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Courtesy of BHG MASIELLO KEENE
The time to sell is now! THE TIME TO SELL IS NOW!
View 190 Ashuelot Street Winchester, NH MLS# 5094108
    Save 190 Ashuelot Street Winchester, NH MLS# 5094108
    1 of 13
    $129,000
    3

    Beds

    1.0

    Baths

    1,457

    Sq.Ft.

    190 Ashuelot Street

    Winchester, NH

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    Courtesy of BHG MASIELLO KEENE
    View 65 Mechanic Street Winchester, NH MLS# 5094140
      Save 65 Mechanic Street Winchester, NH MLS# 5094140
      1 of 19
      $299,900
      4

      Beds

      2.0

      Baths

      2,128

      Sq.Ft.

      65 Mechanic Street

      Winchester, NH

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      Courtesy of BHG MASIELLO KEENE
      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 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

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          Courtesy of COLDWELL BANKER REALTY NASHUA
          View 166 Keene Road Winchester, NH MLS# 5092617
            Save 166 Keene Road Winchester, NH MLS# 5092617
            1 of 60
            $499,900
            3

            Beds

            1.1

            Baths

            1,808

            Sq.Ft.

            166 Keene Road

            Winchester, NH

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            Courtesy of BHG MASIELLO KEENE
            View 20 Lake Shore Drive Winchester, NH MLS# 5091522
              Save 20 Lake Shore Drive Winchester, NH MLS# 5091522
              1 of 8
              $135,000
              Studio

              Beds

              0.0

              Baths

              20 Lake Shore Drive

              Winchester, NH

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              Courtesy of KELLER WILLIAMS REALTY METRO-KEENE
              View 30 Melvin Bridge Road Winchester, NH MLS# 5089356
                Save 30 Melvin Bridge Road Winchester, NH MLS# 5089356
                1 of 52
                $325,000
                4

                Beds

                1.2

                Baths

                1,750

                Sq.Ft.

                30 Melvin Bridge Road

                Winchester, NH

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                Courtesy of BHG MASIELLO KEENE
                View 62 Parker Street Winchester, NH MLS# 5087056
                  Save 62 Parker Street Winchester, NH MLS# 5087056
                  1 of 60
                  $439,900
                  4

                  Beds

                  1.1

                  Baths

                  2,252

                  Sq.Ft.

                  62 Parker Street

                  Winchester, NH

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                  Courtesy of R.H. THACKSTON & COMPANY
                  View 19 Back Ashuelot Road Winchester, NH MLS# 5086470
                    Save 19 Back Ashuelot Road Winchester, NH MLS# 5086470
                    1 of 26
                    $295,000
                    4

                    Beds

                    2.0

                    Baths

                    1,493

                    Sq.Ft.

                    19 Back Ashuelot Road

                    Winchester, NH

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                    Courtesy of EXP REALTY
                    View 26 Mechanic Street Winchester, NH MLS# 5085187
                      Save 26 Mechanic Street Winchester, NH MLS# 5085187
                      1 of 41
                      $384,999
                      4

                      Beds

                      2.1

                      Baths

                      2,736

                      Sq.Ft.

                      26 Mechanic Street

                      Winchester, NH

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                      Courtesy of HKS ASSOCIATES, INC.
                      View 7 Purcell Road Winchester, NH MLS# 5084770
                        Save 7 Purcell Road Winchester, NH MLS# 5084770
                        1 of 22
                        $319,000
                        3

                        Beds

                        1.1

                        Baths

                        1,805

                        Sq.Ft.

                        7 Purcell Road

                        Winchester, NH

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                        Courtesy of CENTURY 21 HIGHVIEW REALTY
                        View 90 Old Swanzey Road Winchester, NH MLS# 5085013
                          Save 90 Old Swanzey Road Winchester, NH MLS# 5085013
                          1 of 8
                          $90,000
                          Studio

                          Beds

                          0.0

                          Baths

                          90 Old Swanzey Road

                          Winchester, NH

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                          Courtesy of R.H. THACKSTON & COMPANY
                          View 0 Tipping Rock Road Winchester, NH MLS# 5084190
                            Save 0 Tipping Rock Road Winchester, NH MLS# 5084190
                            1 of 5
                            $19,500
                            Studio

                            Beds

                            0.0

                            Baths

                            0 Tipping Rock Road

                            Winchester, NH

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                            Courtesy of BLAIS & ASSOCIATES, REALTORS
                            View 69 Plumb Pak Drive Winchester, NH MLS# 5083256
                              Save 69 Plumb Pak Drive Winchester, NH MLS# 5083256
                              1 of 15
                              $89,000
                              Studio

                              Beds

                              0.0

                              Baths

                              69 Plumb Pak Drive

                              Winchester, NH

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                              Courtesy of KELLER WILLIAMS REALTY METRO-KEENE
                              View Map 6 Lot 15-5 Off Opportunity Drive # 15-5 Winchester, NH MLS# 5082298
                                Save Map 6 Lot 15-5 Off Opportunity Drive # 15-5 Winchester, NH MLS# 5082298
                                1 of 21
                                $109,500
                                Studio

                                Beds

                                0.0

                                Baths

                                Map 6 Lot 15-5 Off Opportunity Drive # 15-5

                                Winchester, NH

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                                Courtesy of COLDWELL BANKER REALTY NASHUA
                                View Map 6 Lot 15-0 Off Opportunity Drive # 15-0 Winchester, NH MLS# 5082303
                                  Save Map 6 Lot 15-0 Off Opportunity Drive # 15-0 Winchester, NH MLS# 5082303
                                  1 of 21
                                  $118,200
                                  Studio

                                  Beds

                                  0.0

                                  Baths

                                  Map 6 Lot 15-0 Off Opportunity Drive # 15-0

                                  Winchester, NH

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                                  Courtesy of COLDWELL BANKER REALTY NASHUA
                                  View Map 6 Opportunity Drive # 15-7 Winchester, NH MLS# 5082306
                                    Save Map 6 Opportunity Drive # 15-7 Winchester, NH MLS# 5082306
                                    1 of 21
                                    $131,600
                                    Studio

                                    Beds

                                    0.0

                                    Baths

                                    Map 6 Opportunity Drive # 15-7

                                    Winchester, NH

                                    NNEREN
                                    Courtesy of COLDWELL BANKER REALTY NASHUA

                                    About Winchester

                                    Listings in Winchester, NH

                                    41

                                    Estimated median home price

                                    $299,900
                                    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 - 100K7
                                    $100K - 200K10
                                    $200K - 300K5
                                    $300K - 400K4
                                    $400K - 500K6
                                    $500K - 600K3
                                    $600K - 700K3
                                    $700K - 800K1
                                    $800K - 900K0
                                    $900K - 1M0
                                    $1M - Max2

                                    Homes for Sale by Type in Winchester, NH

                                    Property TypeCount
                                    Single Family17
                                    Townhouse0
                                    Condo0
                                    Commercial2
                                    Rental1
                                    Lots and Land15
                                    Condo/Town/CoOp0
                                    CoOp0
                                    Multi Family5
                                    Mobile Home2
                                    Farms0

                                    (Data as of 7/3/2026)

                                    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 7/5/2026”

                                    Trends Information provided by ATTOM Data Solutions.