Bennington Vermont Homes for Sale

404 total properties
View 3149 West Hill Drive Readsboro, VT MLS# 5107298
    Save 3149 West Hill Drive Readsboro, VT MLS# 5107298
    1 of 46
    $325,000
    2

    Beds

    1.0

    Baths

    976

    Sq.Ft.

    3149 West Hill Drive

    Readsboro, VT

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    Courtesy of MONARCH REALTY
    View 4362 VT Route 11 # 1A Peru, VT MLS# 5109840
      Save 4362 VT Route 11 # 1A Peru, VT MLS# 5109840
      1 of 16
      $325,000
      2

      Beds

      1.0

      Baths

      720

      Sq.Ft.

      4362 VT Route 11 # 1A

      Peru, VT

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      Courtesy of BROMLEY REAL ESTATE
      View 110 Coulter Street Bennington, VT MLS# 5111698
      • Recently Listed
      Save 110 Coulter Street Bennington, VT MLS# 5111698
      1 of 48
      $329,000
      3

      Beds

      1.1

      Baths

      1,563

      Sq.Ft.

      110 Coulter Street

      Bennington, VT

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      Courtesy of MAPLE LEAF REAL ESTATE
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 773 Oberdorf Road Readsboro, VT MLS# 5080881
        Save 773 Oberdorf Road Readsboro, VT MLS# 5080881
        1 of 23
        $329,900
        4

        Beds

        2.0

        Baths

        2,030

        Sq.Ft.

        773 Oberdorf Road

        Readsboro, VT

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        Courtesy of MORESI REAL ESTATE PARTNERS
        View 1141 Burgess Road Bennington, VT MLS# 5106263
          Save 1141 Burgess Road Bennington, VT MLS# 5106263
          1 of 50
          $330,000
          2

          Beds

          1.1

          Baths

          1,750

          Sq.Ft.

          1141 Burgess Road

          Bennington, VT

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          Courtesy of EXP REALTY
          View 30 Slate Circle Manchester, VT MLS# 5110288
            Save 30 Slate Circle Manchester, VT MLS# 5110288
            1 of 28
            $337,000
            2

            Beds

            1.1

            Baths

            1,400

            Sq.Ft.

            30 Slate Circle

            Manchester, VT

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            Courtesy of RE/MAX FOUR SEASONS
            View 81 Holliday Drive Shaftsbury, VT MLS# 5111123
              Save 81 Holliday Drive Shaftsbury, VT MLS# 5111123
              1 of 48
              $339,000
              3

              Beds

              1.1

              Baths

              1,292

              Sq.Ft.

              81 Holliday Drive

              Shaftsbury, VT

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              Courtesy of HOFFMAN REAL ESTATE
              View 19 Winhall Condo Road # 4 Winhall, VT MLS# 5106209
                Save 19 Winhall Condo Road # 4 Winhall, VT MLS# 5106209
                1 of 34
                $345,000
                2

                Beds

                2.0

                Baths

                960

                Sq.Ft.

                19 Winhall Condo Road # 4

                Winhall, VT

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                Courtesy of THE HAVEN GROUP
                View 710 Main Street Bennington, VT MLS# 5102985
                  Save 710 Main Street Bennington, VT MLS# 5102985
                  1 of 4
                  $349,000
                  8

                  Beds

                  4.0

                  Baths

                  3,637

                  Sq.Ft.

                  710 Main Street

                  Bennington, VT

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                  Courtesy of PERROTT REALTY
                  View 21 Russett Drive Bennington, VT MLS# 5104474
                    Save 21 Russett Drive Bennington, VT MLS# 5104474
                    1 of 33
                    $349,000
                    3

                    Beds

                    2.0

                    Baths

                    1,911

                    Sq.Ft.

                    21 Russett Drive

                    Bennington, VT

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                    Courtesy of MAHAR MCCARTHY REAL ESTATE
                    View 390 Smith Drive Readsboro, VT MLS# 5105070
                      Save 390 Smith Drive Readsboro, VT MLS# 5105070
                      1 of 34
                      $349,000
                      2

                      Beds

                      2.0

                      Baths

                      1,808

                      Sq.Ft.

                      390 Smith Drive

                      Readsboro, VT

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                      Courtesy of BHG MASIELLO BRATTLEBORO
                      View 57 Paran Road Shaftsbury, VT MLS# 5106873
                        Save 57 Paran Road Shaftsbury, VT MLS# 5106873
                        1 of 35
                        $349,000
                        3

                        Beds

                        2.0

                        Baths

                        1,616

                        Sq.Ft.

                        57 Paran Road

                        Shaftsbury, VT

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                        Courtesy of MAHAR MCCARTHY REAL ESTATE
                        View 219-221 Washington Avenue Bennington, VT MLS# 5106581
                          Save 219-221 Washington Avenue Bennington, VT MLS# 5106581
                          1 of 36
                          $349,900
                          6

                          Beds

                          4.0

                          Baths

                          2,584

                          Sq.Ft.

                          219-221 Washington Avenue

                          Bennington, VT

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                          Courtesy of HOFFMAN REAL ESTATE
                          View 4378 Route 30 Dorset, VT MLS# 5112032
                          • Recently Listed
                          Save 4378 Route 30 Dorset, VT MLS# 5112032
                          1 of 44
                          $349,900
                          2

                          Beds

                          1.1

                          Baths

                          1,122

                          Sq.Ft.

                          4378 Route 30

                          Dorset, VT

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                          Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
                          View 524 Jennings Brook Drive Bennington, VT MLS# 5090266
                            Save 524 Jennings Brook Drive Bennington, VT MLS# 5090266
                            1 of 4
                            $350,000
                            2

                            Beds

                            2.0

                            Baths

                            1,190

                            Sq.Ft.

                            524 Jennings Brook Drive

                            Bennington, VT

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                            Courtesy of MAPLE LEAF REAL ESTATE
                            View 1111 Old Depot Road Shaftsbury, VT MLS# 5093706
                              Save 1111 Old Depot Road Shaftsbury, VT MLS# 5093706
                              1 of 60
                              $350,000
                              4

                              Beds

                              2.0

                              Baths

                              1,593

                              Sq.Ft.

                              1111 Old Depot Road

                              Shaftsbury, VT

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                              Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
                              View 1253 Old West Road Arlington, VT MLS# 5098377
                                Save 1253 Old West Road Arlington, VT MLS# 5098377
                                1 of 38
                                $350,000
                                2

                                Beds

                                2.0

                                Baths

                                1,648

                                Sq.Ft.

                                1253 Old West Road

                                Arlington, VT

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                                Courtesy of EXP REALTY
                                View 110 Short Street Bennington, VT MLS# 5101907
                                  Save 110 Short Street Bennington, VT MLS# 5101907
                                  1 of 32
                                  $350,000
                                  6

                                  Beds

                                  4.0

                                  Baths

                                  2,586

                                  Sq.Ft.

                                  110 Short Street

                                  Bennington, VT

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                                  Courtesy of MAPLE LEAF REAL ESTATE
                                  View 18 Old Snow Valley Road Winhall, VT MLS# 5108069
                                    Save 18 Old Snow Valley Road Winhall, VT MLS# 5108069
                                    1 of 39
                                    $350,000
                                    3

                                    Beds

                                    2.0

                                    Baths

                                    1,040

                                    Sq.Ft.

                                    18 Old Snow Valley Road

                                    Winhall, VT

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                                    Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
                                    View 261 Skyboro Road Pownal, VT MLS# 5110100
                                      Save 261 Skyboro Road Pownal, VT MLS# 5110100
                                      1 of 39
                                      $350,000
                                      3

                                      Beds

                                      1.1

                                      Baths

                                      1,256

                                      Sq.Ft.

                                      261 Skyboro Road

                                      Pownal, VT

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                                      Courtesy of HOFFMAN REAL ESTATE

                                      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 10/10/2026”

                                      Trends Information provided by ATTOM Data Solutions.