05201 Homes for Sale

110 total properties
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 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 30
      $1,925,000
      5,972

      Sq.Ft.

      226-228 Northside Drive

      Bennington, VT

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      Courtesy of HOFFMAN REAL ESTATE
      The time to sell is now! THE TIME TO SELL IS NOW!
      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
        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
          $1,225,000
          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 153 Northside Drive Bennington, VT MLS# 5092354
              Save 153 Northside Drive Bennington, VT MLS# 5092354
              $997,000

              153 Northside Drive

              Bennington, VT

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              Courtesy of FOUR CORNER PROPERTIES LLC
              View 310 Main Street Bennington, VT MLS# 5094475
              • Recently Listed
              Save 310 Main Street Bennington, VT MLS# 5094475
              1 of 4
              $995,000
              8,875

              Sq.Ft.

              310 Main Street

              Bennington, VT

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              Courtesy of TPW REAL ESTATE
              View 124 Elm Street Bennington, VT MLS# 5072098
                Save 124 Elm Street Bennington, VT MLS# 5072098
                1 of 25
                $950,000
                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 515 Quarry Road Bennington, VT MLS# 5089246
                    • Virtual Tour
                    Save 515 Quarry Road Bennington, VT MLS# 5089246
                    1 of 60
                    $695,000
                    4

                    Beds

                    2.0

                    Baths

                    1,614

                    Sq.Ft.

                    515 Quarry Road

                    Bennington, VT

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                    Courtesy of MAPLE LEAF 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
                        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
                          • 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
                          View 193 Finley Drive Bennington, VT MLS# 5094280
                            Save 193 Finley Drive Bennington, VT MLS# 5094280
                            1 of 43
                            $550,000
                            2

                            Beds

                            2.1

                            Baths

                            3,105

                            Sq.Ft.

                            193 Finley Drive

                            Bennington, 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 6/30/2026”

                            Trends Information provided by ATTOM Data Solutions.