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
        The time to sell is now! THE TIME TO SELL IS NOW!
        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
              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
                        • Virtual Tour
                        Save 3414 Whispering Hills Chester, NY MLS# 974398
                        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
                        • Recently Listed
                        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
                        View 1311 Whispering Hills Chester, NY MLS# 983111
                          Save 1311 Whispering Hills Chester, NY MLS# 983111
                          1 of 32
                          $329,900
                          3

                          Beds

                          2.0

                          Baths

                          1,316

                          Sq.Ft.

                          1311 Whispering Hills

                          Chester, NY

                          Courtesy of KELLER WILLIAMS REALTY
                          View 4118 Whispering Hills Drive Chester, NY MLS# 1018748
                            Save 4118 Whispering Hills Drive Chester, NY MLS# 1018748
                            1 of 22
                            $329,000
                            2

                            Beds

                            1.1

                            Baths

                            1,294

                            Sq.Ft.

                            4118 Whispering Hills Drive

                            Chester, NY

                            Courtesy of HOWARD HANNA RAND REALTY
                            View 151 Main Street Chester, NY MLS# 1031155
                              Save 151 Main Street Chester, NY MLS# 1031155
                              1 of 16
                              $325,000
                              4

                              Beds

                              1.0

                              Baths

                              1,504

                              Sq.Ft.

                              151 Main Street

                              Chester, NY

                              Courtesy of HUDSON VALLEY GRIFFITH
                              View 2820 Whispering Hills Chester, NY MLS# 986005
                                Save 2820 Whispering Hills Chester, NY MLS# 986005
                                1 of 32
                                $319,900
                                2

                                Beds

                                1.1

                                Baths

                                1,072

                                Sq.Ft.

                                2820 Whispering Hills

                                Chester, NY

                                Courtesy of R2M REALTY INC.
                                View 552 Pine Hill Road Chester, NY MLS# 958740
                                  Save 552 Pine Hill Road Chester, NY MLS# 958740
                                  1 of 1
                                  $299,000
                                  Studio

                                  Beds

                                  0.0

                                  Baths

                                  248,292

                                  Sq.Ft.

                                  552 Pine Hill Road

                                  Chester, NY

                                  Courtesy of EREALTY ADVISORS, INC
                                  View 2113 Whispering Hills Chester, NY MLS# 950534
                                    Save 2113 Whispering Hills Chester, NY MLS# 950534
                                    1 of 24
                                    $295,000
                                    2

                                    Beds

                                    1.0

                                    Baths

                                    1,084

                                    Sq.Ft.

                                    2113 Whispering Hills

                                    Chester, NY

                                    Courtesy of KELLER WILLIAMS REALTY
                                    View 2119 Whispering Hills Chester, NY MLS# 1019548
                                      Save 2119 Whispering Hills Chester, NY MLS# 1019548
                                      1 of 32
                                      $295,000
                                      2

                                      Beds

                                      1.1

                                      Baths

                                      1,086

                                      Sq.Ft.

                                      2119 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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