View 21 Winding Hill Brattleboro, VT MLS# 5107649
    Save 21 Winding Hill Brattleboro, VT MLS# 5107649
    1 of 24
    $120,000
    2

    Beds

    1.0

    Baths

    924

    Sq.Ft.

    21 Winding Hill

    Brattleboro, VT

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    Courtesy of BRATTLEBORO AREA REALTY
    View 39 Brookside Drive # 5 Brattleboro, VT MLS# 5107706
      Save 39 Brookside Drive # 5 Brattleboro, VT MLS# 5107706
      1 of 21
      $190,000
      2

      Beds

      1.0

      Baths

      930

      Sq.Ft.

      39 Brookside Drive # 5

      Brattleboro, VT

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      Courtesy of BRATTLEBORO AREA REALTY
      View 11 Crescent Drive Brattleboro, VT MLS# 5107263
        Save 11 Crescent Drive Brattleboro, VT MLS# 5107263
        1 of 34
        $16,900
        2

        Beds

        1.0

        Baths

        672

        Sq.Ft.

        11 Crescent Drive

        Brattleboro, VT

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        Courtesy of BHG MASIELLO BRATTLEBORO
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 77 Buttonwood Drive Brattleboro, VT MLS# 5106541
        • Adult Community
        Save 77 Buttonwood Drive Brattleboro, VT MLS# 5106541
        1 of 17
        $439,000
        2

        Beds

        2.0

        Baths

        1,550

        Sq.Ft.

        77 Buttonwood Drive

        Brattleboro, VT

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        Courtesy of BRATTLEBORO AREA REALTY
        View 1137 Upper Dummerston Road Brattleboro, VT MLS# 5105327
          Save 1137 Upper Dummerston Road Brattleboro, VT MLS# 5105327
          1 of 41
          $439,000
          3

          Beds

          2.0

          Baths

          1,600

          Sq.Ft.

          1137 Upper Dummerston Road

          Brattleboro, VT

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          Courtesy of BRATTLEBORO AREA REALTY
          View 207 Elliot Street Brattleboro, VT MLS# 5105369
            Save 207 Elliot Street Brattleboro, VT MLS# 5105369
            1 of 26
            $290,000
            5

            Beds

            1.0

            Baths

            2,167

            Sq.Ft.

            207 Elliot Street

            Brattleboro, VT

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            Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
            View 13 Winding Hill Road Brattleboro, VT MLS# 5104665
              Save 13 Winding Hill Road Brattleboro, VT MLS# 5104665
              1 of 23
              $115,000
              2

              Beds

              2.0

              Baths

              1,222

              Sq.Ft.

              13 Winding Hill Road

              Brattleboro, VT

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              Courtesy of BRATTLEBORO AREA REALTY
              View 147 Morningside Commons Brattleboro, VT MLS# 5104720
                Save 147 Morningside Commons Brattleboro, VT MLS# 5104720
                1 of 50
                $250,000
                2

                Beds

                1.1

                Baths

                1,056

                Sq.Ft.

                147 Morningside Commons

                Brattleboro, VT

                NNEREN
                Courtesy of BHG MASIELLO BRATTLEBORO
                View 116 Green Meadow Road Brattleboro, VT MLS# 5104900
                  Save 116 Green Meadow Road Brattleboro, VT MLS# 5104900
                  1 of 59
                  $390,000
                  2

                  Beds

                  3.0

                  Baths

                  1,614

                  Sq.Ft.

                  116 Green Meadow Road

                  Brattleboro, VT

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                  Courtesy of KELLER WILLIAMS REALTY METRO-KEENE
                  View 68 East Bonnyvale Lane Brattleboro, VT MLS# 5103897
                    Save 68 East Bonnyvale Lane Brattleboro, VT MLS# 5103897
                    1 of 30
                    $299,000
                    3

                    Beds

                    2.0

                    Baths

                    1,400

                    Sq.Ft.

                    68 East Bonnyvale Lane

                    Brattleboro, VT

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                    Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
                    View 203 Fairview Street Brattleboro, VT MLS# 5103959
                      Save 203 Fairview Street Brattleboro, VT MLS# 5103959
                      1 of 35
                      $305,000
                      2

                      Beds

                      1.0

                      Baths

                      640

                      Sq.Ft.

                      203 Fairview Street

                      Brattleboro, VT

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                      Courtesy of BRATTLEBORO AREA REALTY
                      View 110 Western Avenue Brattleboro, VT MLS# 5103506
                        Save 110 Western Avenue Brattleboro, VT MLS# 5103506
                        1 of 29
                        $289,000
                        4

                        Beds

                        2.0

                        Baths

                        1,860

                        Sq.Ft.

                        110 Western Avenue

                        Brattleboro, VT

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                        Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
                        View 72 Green Meadow Brattleboro, VT MLS# 5103012
                          Save 72 Green Meadow Brattleboro, VT MLS# 5103012
                          1 of 27
                          $450,000
                          3

                          Beds

                          2.0

                          Baths

                          2,530

                          Sq.Ft.

                          72 Green Meadow

                          Brattleboro, VT

                          NNEREN
                          Courtesy of BERKLEY & VELLER GREENWOOD COUNTRY
                          View 30 Lexington Avenue Brattleboro, VT MLS# 5103014
                            Save 30 Lexington Avenue Brattleboro, VT MLS# 5103014
                            1 of 24
                            $295,000
                            3

                            Beds

                            1.0

                            Baths

                            1,092

                            Sq.Ft.

                            30 Lexington Avenue

                            Brattleboro, VT

                            NNEREN
                            Courtesy of BRATTLEBORO AREA REALTY
                            View 9 Village Drive Brattleboro, VT MLS# 5102920
                              Save 9 Village Drive Brattleboro, VT MLS# 5102920
                              1 of 24
                              $59,000
                              2

                              Beds

                              1.0

                              Baths

                              744

                              Sq.Ft.

                              9 Village Drive

                              Brattleboro, VT

                              NNEREN
                              Courtesy of BRATTLEBORO AREA REALTY
                              View 0 Pleasant Valley Road Brattleboro, VT MLS# 5102764
                                Save 0 Pleasant Valley Road Brattleboro, VT MLS# 5102764
                                1 of 9
                                $198,000
                                0.0

                                Baths

                                0 Pleasant Valley Road

                                Brattleboro, VT

                                NNEREN
                                Courtesy of BRATTLEBORO AREA REALTY
                                View 138 Wantastiquet Drive Brattleboro, VT MLS# 5102500
                                  Save 138 Wantastiquet Drive Brattleboro, VT MLS# 5102500
                                  1 of 31
                                  $415,000
                                  3

                                  Beds

                                  2.0

                                  Baths

                                  1,934

                                  Sq.Ft.

                                  138 Wantastiquet Drive

                                  Brattleboro, VT

                                  NNEREN
                                  Courtesy of BRATTLEBORO AREA REALTY
                                  View 120 Western Avenue Brattleboro, VT MLS# 5100544
                                    Save 120 Western Avenue Brattleboro, VT MLS# 5100544
                                    1 of 42
                                    $340,000
                                    4

                                    Beds

                                    2.0

                                    Baths

                                    2,745

                                    Sq.Ft.

                                    120 Western Avenue

                                    Brattleboro, VT

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                                    Courtesy of ACORN REAL ESTATE GROUP LLC
                                    View 117 * Fuller Drive Brattleboro, VT MLS# 5099250
                                      Save 117 * Fuller Drive Brattleboro, VT MLS# 5099250
                                      1 of 17
                                      $110,000
                                      0.0

                                      Baths

                                      117 * Fuller Drive

                                      Brattleboro, VT

                                      NNEREN
                                      Courtesy of BRATTLEBORO AREA REALTY
                                      View 11 Evergreen Lane Brattleboro, VT MLS# 5099302
                                        Save 11 Evergreen Lane Brattleboro, VT MLS# 5099302
                                        1 of 27
                                        $230,000
                                        2

                                        Beds

                                        1.1

                                        Baths

                                        1,248

                                        Sq.Ft.

                                        11 Evergreen Lane

                                        Brattleboro, VT

                                        NNEREN
                                        Courtesy of BARRETT & VALLEY ASSOC. INC

                                        About Brattleboro

                                        Listings in Brattleboro, VT

                                        90

                                        Estimated median home price

                                        $305,000
                                        Brattleboro VT Homes for Sale & Properties

                                        Weichert Realtors is one of the nation's leading providers of Brattleboro, Vermont real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Brattleboro, VT.

                                        Homes for Sale by Price in Brattleboro, VT

                                        PriceCount
                                        $0 - 100K4
                                        $100K - 200K16
                                        $200K - 300K24
                                        $300K - 400K20
                                        $400K - 500K13
                                        $500K - 600K6
                                        $600K - 700K1
                                        $700K - 800K1
                                        $800K - 900K1
                                        $900K - 1M1
                                        $1M - Max3

                                        Homes for Sale by Type in Brattleboro, VT

                                        Property TypeCount
                                        Single Family35
                                        Townhouse0
                                        Condo11
                                        Commercial13
                                        Rental9
                                        Lots and Land8
                                        Condo/Town/CoOp0
                                        CoOp0
                                        Multi Family17
                                        Mobile Home6
                                        Farms0

                                        (Data as of 10/2/2026)

                                        Find Properties in Brattleboro, VT

                                        Brattleboro, VT 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 10/3/2026”

                                        Trends Information provided by ATTOM Data Solutions.