View Main Street Chester, NY MLS# H6204360
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    1 of 2
    $500,000
    Studio

    Beds

    0.0

    Baths

    36,098

    Sq.Ft.

    Main Street

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 5 N Hudson Street Chester, NY MLS# 976521
      Save 5 N Hudson Street Chester, NY MLS# 976521
      1 of 28
      $500,000
      3

      Beds

      2.0

      Baths

      2,688

      Sq.Ft.

      5 N Hudson Street

      Chester, NY

      Courtesy of KELLER WILLIAMS REALTY
      View 37 Surrey Road Chester, NY MLS# 1007164
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      Save 37 Surrey Road Chester, NY MLS# 1007164
      1 of 40
      $500,000
      4

      Beds

      2.0

      Baths

      1,730

      Sq.Ft.

      37 Surrey Road

      Chester, NY

      Courtesy of EXP REALTY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 35 Maple Avenue Chester, NY MLS# 990509
        Save 35 Maple Avenue Chester, NY MLS# 990509
        1 of 29
        $489,900
        3

        Beds

        3.0

        Baths

        2,032

        Sq.Ft.

        35 Maple Avenue

        Chester, NY

        Courtesy of RE/MAX BENCHMARK REALTY GROUP
        View 76 Surrey Road Chester, NY MLS# 1022518
          Save 76 Surrey Road Chester, NY MLS# 1022518
          1 of 44
          $489,900
          3

          Beds

          2.0

          Baths

          1,912

          Sq.Ft.

          76 Surrey Road

          Chester, NY

          Courtesy of EXP REALTY
          View 32 Surrey Road Chester, NY MLS# 1040785
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          1 of 39
          $489,000
          4

          Beds

          1.1

          Baths

          1,820

          Sq.Ft.

          32 Surrey Road

          Chester, NY

          Courtesy of EXP REALTY
          View 21 Trotting Drive Chester, NY MLS# 1030740
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          Save 21 Trotting Drive Chester, NY MLS# 1030740
          1 of 50
          $475,000
          3

          Beds

          2.0

          Baths

          1,624

          Sq.Ft.

          21 Trotting Drive

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 70 Main Street Chester, NY MLS# 1034449
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          1 of 27
          $469,000
          3

          Beds

          1.2

          Baths

          1,357

          Sq.Ft.

          70 Main Street

          Chester, NY

          Courtesy of CURASI REALTY, INC.
          View 63 Hubshop Road Chester, NY MLS# 1039933
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          Save 63 Hubshop Road Chester, NY MLS# 1039933
          1 of 19
          $459,000
          4

          Beds

          2.1

          Baths

          2,060

          Sq.Ft.

          63 Hubshop Road

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 66 Whitetail Run Chester, NY MLS# 1033721
            Save 66 Whitetail Run Chester, NY MLS# 1033721
            1 of 50
            $449,000
            3

            Beds

            1.1

            Baths

            1,500

            Sq.Ft.

            66 Whitetail Run

            Chester, NY

            Courtesy of HOWARD HANNA RAND REALTY
            View 1367 Kings Highway Chester, NY MLS# 1036770
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            1 of 16
            $440,000
            3

            Beds

            1.1

            Baths

            1,728

            Sq.Ft.

            1367 Kings Highway

            Chester, NY

            Courtesy of GREENE REALTY GROUP
            View 151 Laroe Road Chester, NY MLS# 995916
              Save 151 Laroe Road Chester, NY MLS# 995916
              1 of 43
              $430,000
              3

              Beds

              1.1

              Baths

              1,177

              Sq.Ft.

              151 Laroe Road

              Chester, NY

              Courtesy of KELLER WILLIAMS REALTY
              View 16 Oakland Avenue Chester, NY MLS# 939522
                Save 16 Oakland Avenue Chester, NY MLS# 939522
                1 of 49
                $425,000
                4

                Beds

                2.1

                Baths

                2,090

                Sq.Ft.

                16 Oakland Avenue

                Chester, NY

                Courtesy of BHG REAL ESTATE GREEN TEAM
                View 11 Oxford Depot Chester, NY MLS# 1002651
                  Save 11 Oxford Depot Chester, NY MLS# 1002651
                  1 of 26
                  $425,000
                  3

                  Beds

                  2.0

                  Baths

                  1,748

                  Sq.Ft.

                  11 Oxford Depot

                  Chester, NY

                  Courtesy of KELLER WILLIAMS REALTY
                  View 492 Black Meadow Road Chester, NY MLS# 1002697
                    Save 492 Black Meadow Road Chester, NY MLS# 1002697
                    1 of 18
                    $399,000
                    Studio

                    Beds

                    0.0

                    Baths

                    2,003,760

                    Sq.Ft.

                    492 Black Meadow Road

                    Chester, NY

                    Courtesy of EXP REALTY
                    View 4114 Whispering Hills Chester, NY MLS# 1027245
                      Save 4114 Whispering Hills Chester, NY MLS# 1027245
                      1 of 29
                      $389,900
                      3

                      Beds

                      2.0

                      Baths

                      1,393

                      Sq.Ft.

                      4114 Whispering Hills

                      Chester, NY

                      Courtesy of COLDWELL BANKER REALTY
                      View 185 Oxford Road Chester, NY MLS# 1019170
                        Save 185 Oxford Road Chester, NY MLS# 1019170
                        1 of 49
                        $389,000
                        3

                        Beds

                        1.0

                        Baths

                        1,062

                        Sq.Ft.

                        185 Oxford Road

                        Chester, NY

                        Courtesy of KELLER WILLIAMS HUDSON VALLEY
                        View 7 Hambletonian Avenue Chester, NY MLS# 964090
                          Save 7 Hambletonian Avenue Chester, NY MLS# 964090
                          1 of 26
                          $379,900
                          2

                          Beds

                          1.0

                          Baths

                          1,026

                          Sq.Ft.

                          7 Hambletonian Avenue

                          Chester, NY

                          Courtesy of HOMESMART HOMES & ESTATES
                          View 3815 Whispering Hills Drive Chester, NY MLS# 1000359
                            Save 3815 Whispering Hills Drive Chester, NY MLS# 1000359
                            1 of 50
                            $370,000
                            3

                            Beds

                            2.1

                            Baths

                            1,331

                            Sq.Ft.

                            3815 Whispering Hills Drive

                            Chester, NY

                            Courtesy of MK REALTY INC
                            View 2522 Whispering Hills Chester, NY MLS# 1027103
                              Save 2522 Whispering Hills Chester, NY MLS# 1027103
                              1 of 35
                              $369,000
                              3

                              Beds

                              2.1

                              Baths

                              1,331

                              Sq.Ft.

                              2522 Whispering Hills

                              Chester, NY

                              Courtesy of HOWARD HANNA RAND REALTY

                              About Chester

                              Listings in Chester, NY

                              108

                              Estimated median home price

                              $699,450
                              Chester NY Homes for Sale & Properties

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

                              Homes for Sale by Price in Chester, NY

                              PriceCount
                              $0 - 100K0
                              $100K - 200K0
                              $200K - 300K5
                              $300K - 400K17
                              $400K - 500K14
                              $500K - 600K9
                              $600K - 700K13
                              $700K - 800K20
                              $800K - 900K12
                              $900K - 1M6
                              $1M - Max12

                              Homes for Sale by Type in Chester, NY

                              Property TypeCount
                              Single Family82
                              Townhouse0
                              Condo14
                              Commercial5
                              Rental23
                              Lots and Land5
                              Condo/Town/CoOp0
                              CoOp0
                              Multi Family2
                              Mobile Home0
                              Farms0

                              (Data as of 8/24/2026)

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                              Information deemed reliable but not guaranteed.

                              The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

                              The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

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