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
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 1367 Kings Highway Chester, NY MLS# 1036770
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      1 of 16
      $440,000
      3

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      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 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 2921 Whispering Hills Chester, NY MLS# 1043986
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                  1 of 42
                  $374,900
                  3

                  Beds

                  2.1

                  Baths

                  1,331

                  Sq.Ft.

                  2921 Whispering Hills

                  Chester, NY

                  Courtesy of ARC REALTY 1 IN SALES
                  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
                      View 2703 Whispering Hills Chester, NY MLS# 1016415
                        Save 2703 Whispering Hills Chester, NY MLS# 1016415
                        1 of 39
                        $365,000
                        3

                        Beds

                        2.1

                        Baths

                        1,331

                        Sq.Ft.

                        2703 Whispering Hills

                        Chester, NY

                        Courtesy of KELLER WILLIAMS REALTY
                        View 3409 Whispering Hills Chester, NY MLS# 1032618
                          Save 3409 Whispering Hills Chester, NY MLS# 1032618
                          1 of 1
                          $360,000
                          3

                          Beds

                          2.1

                          Baths

                          1,331

                          Sq.Ft.

                          3409 Whispering Hills

                          Chester, NY

                          Courtesy of HOWARD HANNA RAND REALTY
                          View 2 Virginia Lane Chester, NY MLS# H6215339
                            Save 2 Virginia Lane Chester, NY MLS# H6215339
                            1 of 4
                            $350,000
                            Studio

                            Beds

                            0.0

                            Baths

                            235,224

                            Sq.Ft.

                            2 Virginia Lane

                            Chester, NY

                            Courtesy of KELLER WILLIAMS REALTY
                            View 220 Oxford Road Chester, NY MLS# 907969
                              Save 220 Oxford Road Chester, NY MLS# 907969
                              1 of 1
                              $350,000
                              Studio

                              Beds

                              0.0

                              Baths

                              274,428

                              Sq.Ft.

                              220 Oxford Road

                              Chester, NY

                              Courtesy of EXIT REALTY VENTURE
                              View 2604 Whispering Hills Chester, NY MLS# 1025165
                                Save 2604 Whispering Hills Chester, NY MLS# 1025165
                                1 of 35
                                $350,000
                                3

                                Beds

                                2.1

                                Baths

                                1,086

                                Sq.Ft.

                                2604 Whispering Hills

                                Chester, NY

                                Courtesy of HOMESMART HOMES & ESTATES
                                View 3414 Whispering Hills Chester, NY MLS# 974398
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                                1 of 34
                                $349,999
                                3

                                Beds

                                2.0

                                Baths

                                1,316

                                Sq.Ft.

                                3414 Whispering Hills

                                Chester, NY

                                Courtesy of KW HUDSON VALLEY UNITED
                                View 166 Bull Mill Road Chester, NY MLS# 1030923
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                                Save 166 Bull Mill Road Chester, NY MLS# 1030923
                                1 of 37
                                $340,000
                                2

                                Beds

                                1.0

                                Baths

                                1,004

                                Sq.Ft.

                                166 Bull Mill Road

                                Chester, NY

                                Courtesy of KELLER WILLIAMS VALLEY REALTY

                                About Chester

                                Listings in Chester, NY

                                112

                                Estimated median home price

                                $692,000
                                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 - 100K1
                                $100K - 200K0
                                $200K - 300K7
                                $300K - 400K17
                                $400K - 500K14
                                $500K - 600K10
                                $600K - 700K13
                                $700K - 800K21
                                $800K - 900K11
                                $900K - 1M6
                                $1M - Max12

                                Homes for Sale by Type in Chester, NY

                                Property TypeCount
                                Single Family83
                                Townhouse0
                                Condo16
                                Commercial6
                                Rental23
                                Lots and Land5
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family2
                                Mobile Home0
                                Farms0

                                (Data as of 8/27/2026)

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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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