View 1876 Popple Dungeon Road Chester, VT MLS# 5075068
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1 of 16
$205,000
3

Beds

0.2

Baths

1,232

Sq.Ft.

1876 Popple Dungeon Road

Chester, VT

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Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
View TBD Farrar Road Chester, VT MLS# 5074848
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1 of 16
$74,500
Studio

Beds

0.0

Baths

TBD Farrar Road

Chester, VT

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Courtesy of EXP REALTY
View 3466 VT Route 103 N Chester, VT MLS# 5074728
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Save 3466 VT Route 103 N Chester, VT MLS# 5074728
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$399,000
2

Beds

2.0

Baths

2,751

Sq.Ft.

3466 VT Route 103 N

Chester, VT

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Courtesy of REAL BROKER LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 469 Williams Road Chester, VT MLS# 5074309
    Save 469 Williams Road Chester, VT MLS# 5074309
    1 of 10
    $129,000
    Studio

    Beds

    0.0

    Baths

    469 Williams Road

    Chester, VT

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    Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
    View 688 Hidden Heights Road Chester, VT MLS# 5074094
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    1 of 60
    $649,000
    3

    Beds

    2.0

    Baths

    2,205

    Sq.Ft.

    688 Hidden Heights Road

    Chester, VT

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    Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
    View 1397 Popple Dungeon Road Chester, VT MLS# 5073930
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    1 of 31
    $399,000
    3

    Beds

    2.0

    Baths

    1,788

    Sq.Ft.

    1397 Popple Dungeon Road

    Chester, VT

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    Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
    View 818 Davidson Hill Road Chester, VT MLS# 5073287
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      1 of 40
      $280,000
      3

      Beds

      2.0

      Baths

      1,248

      Sq.Ft.

      818 Davidson Hill Road

      Chester, VT

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      Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
      View 40 Fenton Road Chester, VT MLS# 5073147
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      Save 40 Fenton Road Chester, VT MLS# 5073147
      1 of 37
      $399,000
      4

      Beds

      2.1

      Baths

      2,148

      Sq.Ft.

      40 Fenton Road

      Chester, VT

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      Courtesy of TPW REAL ESTATE
      View 531 Main Street Chester, VT MLS# 5070720
        Save 531 Main Street Chester, VT MLS# 5070720
        1 of 53
        $390,000
        3

        Beds

        1.0

        Baths

        1,608

        Sq.Ft.

        531 Main Street

        Chester, VT

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        Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
        View 810 Quarry Road Chester, VT MLS# 5070079
          Save 810 Quarry Road Chester, VT MLS# 5070079
          1 of 60
          $815,000
          3

          Beds

          2.1

          Baths

          2,466

          Sq.Ft.

          810 Quarry Road

          Chester, VT

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          Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES
          View 41 VT Route 103 South Chester, VT MLS# 5070146
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          Save 41 VT Route 103 South Chester, VT MLS# 5070146
          1 of 33
          $299,000
          Studio

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          0.0

          Baths

          2,702

          Sq.Ft.

          41 VT Route 103 South

          Chester, VT

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          Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
          View 00 Contro Road Chester, VT MLS# 5069927
            Save 00 Contro Road Chester, VT MLS# 5069927
            1 of 3
            $159,000
            Studio

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            0.0

            Baths

            00 Contro Road

            Chester, VT

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            Courtesy of BRATTLEBORO AREA REALTY
            View 106 Contro Road Chester, VT MLS# 5069928
              Save 106 Contro Road Chester, VT MLS# 5069928
              1 of 14
              $289,000
              2

              Beds

              2.1

              Baths

              1,475

              Sq.Ft.

              106 Contro Road

              Chester, VT

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              Courtesy of BRATTLEBORO AREA REALTY
              View 514 First Avenue Chester, VT MLS# 5068855
                Save 514 First Avenue Chester, VT MLS# 5068855
                1 of 37
                $529,000
                5

                Beds

                5.0

                Baths

                3,880

                Sq.Ft.

                514 First Avenue

                Chester, VT

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                Courtesy of BARRETT AND VALLEY ASSOCIATES INC.
                View 00 Remington Road Chester, VT MLS# 5061671
                  Save 00 Remington Road Chester, VT MLS# 5061671
                  1 of 14
                  $74,000
                  Studio

                  Beds

                  0.0

                  Baths

                  00 Remington Road

                  Chester, VT

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                  Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
                  View 447 Elm Street Chester, VT MLS# 5061241
                    Save 447 Elm Street Chester, VT MLS# 5061241
                    1 of 27
                    $369,000
                    3

                    Beds

                    2.0

                    Baths

                    1,488

                    Sq.Ft.

                    447 Elm Street

                    Chester, VT

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                    Courtesy of CUMMINGS & CO
                    View 1175 Quarry Road Chester, VT MLS# 5058824
                      Save 1175 Quarry Road Chester, VT MLS# 5058824
                      1 of 22
                      $290,000
                      Studio

                      Beds

                      0.0

                      Baths

                      1175 Quarry Road

                      Chester, VT

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                      Courtesy of BHG MASIELLO KEENE
                      View 918 Lovers Lane Road Chester, VT MLS# 5058859
                        Save 918 Lovers Lane Road Chester, VT MLS# 5058859
                        1 of 21
                        $145,000
                        Studio

                        Beds

                        0.0

                        Baths

                        918 Lovers Lane Road

                        Chester, VT

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                        Courtesy of NORTHLAND REAL ESTATE
                        View 95 Church Street Chester, VT MLS# 5054818
                          Save 95 Church Street Chester, VT MLS# 5054818
                          1 of 52
                          $625,000
                          4

                          Beds

                          3.0

                          Baths

                          2,794

                          Sq.Ft.

                          95 Church Street

                          Chester, VT

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                          Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.
                          View 3553 VT Route 103 N Chester, VT MLS# 5053765
                            Save 3553 VT Route 103 N Chester, VT MLS# 5053765
                            1 of 19
                            $164,000
                            2,400

                            Sq.Ft.

                            3553 VT Route 103 N

                            Chester, VT

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                            Courtesy of BARRETT AND VALLEY ASSOCIATES INC.

                            About Chester

                            Listings in Chester, VT

                            36

                            Estimated median home price

                            $284,500
                            Chester VT Homes for Sale & Properties

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

                            Homes for Sale by Price in Chester, VT

                            PriceCount
                            $0 - 100K3
                            $100K - 200K8
                            $200K - 300K10
                            $300K - 400K4
                            $400K - 500K2
                            $500K - 600K4
                            $600K - 700K4
                            $700K - 800K0
                            $800K - 900K1
                            $900K - 1M0
                            $1M - Max0

                            Homes for Sale by Type in Chester, VT

                            Property TypeCount
                            Single Family16
                            Townhouse0
                            Condo0
                            Commercial4
                            Rental1
                            Lots and Land12
                            Condo/Town/CoOp0
                            CoOp0
                            Multi Family3
                            Mobile Home1
                            Farms0

                            (Data as of 1/29/2026)

                            Find Properties in Chester, VT

                            Chester, 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 1/30/2026”

                            Trends Information provided by ATTOM Data Solutions.