05201 Homes for Sale

102 total properties
View 230 School Street Bennington, VT MLS# 5058163
    Save 230 School Street Bennington, VT MLS# 5058163
    1 of 21
    $2,950,000
    75,000

    Sq.Ft.

    230 School Street

    Bennington, VT

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    Courtesy of TPW REAL ESTATE
    View 301 Northside Drive Bennington, VT MLS# 5072776
      Save 301 Northside Drive Bennington, VT MLS# 5072776
      1 of 1
      $2,190,000
      Studio

      Beds

      0.0

      Baths

      301 Northside Drive

      Bennington, VT

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      Courtesy of TPW REAL ESTATE
      View 720 North Branch Street Bennington, VT MLS# 5047411
        Save 720 North Branch Street Bennington, VT MLS# 5047411
        1 of 10
        $1,950,000
        Studio

        Beds

        0.0

        Baths

        720 North Branch Street

        Bennington, VT

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        Courtesy of TPW REAL ESTATE
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 1086 West Road Bennington, VT MLS# 5074314
        • Virtual Tour
        Save 1086 West Road Bennington, VT MLS# 5074314
        1 of 58
        $1,950,000
        9

        Beds

        5.2

        Baths

        6,956

        Sq.Ft.

        1086 West Road

        Bennington, VT

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        Courtesy of MAHAR MCCARTHY REAL ESTATE
        View 226-228 Northside Drive Bennington, VT MLS# 5074956
          Save 226-228 Northside Drive Bennington, VT MLS# 5074956
          1 of 25
          $1,925,000
          5,972

          Sq.Ft.

          226-228 Northside Drive

          Bennington, VT

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          Courtesy of HOFFMAN REAL ESTATE
          View 16 West Road Bennington, VT MLS# 5075253
          • Virtual Tour
          Save 16 West Road Bennington, VT MLS# 5075253
          1 of 58
          $1,495,000
          7

          Beds

          5.1

          Baths

          6,392

          Sq.Ft.

          16 West Road

          Bennington, VT

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          Courtesy of MAHAR MCCARTHY REAL ESTATE
          View 116 Northside Drive Bennington, VT MLS# 5087810
          • Recently Listed
          Save 116 Northside Drive Bennington, VT MLS# 5087810
          1 of 3
          $1,400,000

          116 Northside Drive

          Bennington, VT

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          Courtesy of TPW REAL ESTATE
          View 126 Elm Street Bennington, VT MLS# 5042623
            Save 126 Elm Street Bennington, VT MLS# 5042623
            1 of 25
            $1,299,000
            7,126

            Sq.Ft.

            126 Elm Street

            Bennington, VT

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            Courtesy of TPW REAL ESTATE
            View 124 Elm Street Bennington, VT MLS# 5029040
            • Virtual Tour
            Save 124 Elm Street Bennington, VT MLS# 5029040
            1 of 44
            $1,250,000
            9,252

            Sq.Ft.

            124 Elm Street

            Bennington, VT

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            Courtesy of TPW REAL ESTATE
            View 153 Northside Drive Bennington, VT MLS# 5081713
              Save 153 Northside Drive Bennington, VT MLS# 5081713
              1 of 7
              $997,000
              Studio

              Beds

              0.0

              Baths

              153 Northside Drive

              Bennington, VT

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              Courtesy of FOUR CORNER PROPERTIES LLC
              View 124 Elm Street Bennington, VT MLS# 5072098
                Save 124 Elm Street Bennington, VT MLS# 5072098
                1 of 25
                $975,000
                Studio

                Beds

                0.0

                Baths

                8,888

                Sq.Ft.

                124 Elm Street

                Bennington, VT

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                Courtesy of TPW REAL ESTATE
                View 736 Main Street Bennington, VT MLS# 5060023
                  Save 736 Main Street Bennington, VT MLS# 5060023
                  1 of 54
                  $825,000
                  12,868

                  Sq.Ft.

                  736 Main Street

                  Bennington, VT

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                  Courtesy of MAPLE LEAF REAL ESTATE
                  View 159 Phyllis Lane Bennington, VT MLS# 5081088
                    Save 159 Phyllis Lane Bennington, VT MLS# 5081088
                    1 of 39
                    $800,000

                    159 Phyllis Lane

                    Bennington, VT

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                    Courtesy of TPW REAL ESTATE
                    View 704 Fox Hill Road Bennington, VT MLS# 5061361
                      Save 704 Fox Hill Road Bennington, VT MLS# 5061361
                      1 of 35
                      $645,000
                      3

                      Beds

                      2.0

                      Baths

                      1,535

                      Sq.Ft.

                      704 Fox Hill Road

                      Bennington, VT

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                      Courtesy of HOFFMAN REAL ESTATE
                      View 682 Fox Hill Road Bennington, VT MLS# 5061356
                        Save 682 Fox Hill Road Bennington, VT MLS# 5061356
                        1 of 47
                        $625,000
                        3

                        Beds

                        2.0

                        Baths

                        1,416

                        Sq.Ft.

                        682 Fox Hill Road

                        Bennington, VT

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                        Courtesy of HOFFMAN REAL ESTATE
                        View 58 Mount Anthony Road Bennington, VT MLS# 5067086
                        • Virtual Tour
                        Save 58 Mount Anthony Road Bennington, VT MLS# 5067086
                        1 of 53
                        $599,000
                        3

                        Beds

                        2.1

                        Baths

                        2,715

                        Sq.Ft.

                        58 Mount Anthony Road

                        Bennington, VT

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                        Courtesy of MAHAR MCCARTHY REAL ESTATE
                        View 125 North Street Bennington, VT MLS# 5036917
                          Save 125 North Street Bennington, VT MLS# 5036917
                          1 of 30
                          $590,000
                          3,725

                          Sq.Ft.

                          125 North Street

                          Bennington, VT

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                          Courtesy of HARSCH ASSOCIATES
                          View 856 Matteson Road Bennington, VT MLS# 5085559
                          • Recently Listed
                          Save 856 Matteson Road Bennington, VT MLS# 5085559
                          1 of 43
                          $579,000
                          3

                          Beds

                          2.0

                          Baths

                          2,501

                          Sq.Ft.

                          856 Matteson Road

                          Bennington, VT

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                          Courtesy of MAPLE LEAF REAL ESTATE
                          View 203-205 Northside Drive Bennington, VT MLS# 5039813
                            Save 203-205 Northside Drive Bennington, VT MLS# 5039813
                            1 of 22
                            $575,000
                            3,698

                            Sq.Ft.

                            203-205 Northside Drive

                            Bennington, VT

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                            Courtesy of MAHAR MCCARTHY REAL ESTATE
                            View 971 South Stream Road Bennington, VT MLS# 5088350
                            • Recently Listed with Virtual Tour
                            Save 971 South Stream Road Bennington, VT MLS# 5088350
                            1 of 41
                            $550,000
                            5

                            Beds

                            2.0

                            Baths

                            1,974

                            Sq.Ft.

                            971 South Stream Road

                            Bennington, VT

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                            Courtesy of MAHAR MCCARTHY 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 5/14/2026”

                            Trends Information provided by ATTOM Data Solutions.