View 70 Main Street Chester, NY MLS# 1034449
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    1 of 27
    $419,000
    3

    Beds

    1.2

    Baths

    1,357

    Sq.Ft.

    70 Main Street

    Chester, NY

    Courtesy of CURASI REALTY, INC.
    View 66 Whitetail Run Chester, NY MLS# 1033721
      Save 66 Whitetail Run Chester, NY MLS# 1033721
      1 of 50
      OPEN HOUSE: Saturday 10/17 12:00 PM - 2:00 PM
      $399,999
      3

      Beds

      1.1

      Baths

      1,500

      Sq.Ft.

      66 Whitetail Run

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View TBD Rt-17M Chester, NY MLS# 1059544
      • Recently Listed
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      1 of 2
      $399,999
      30,000

      Sq.Ft.

      TBD Rt-17M

      Chester, NY

      Courtesy of EREALTY ADVISORS, INC
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 492 Black Meadow Road Chester, NY MLS# 1002697
        Save 492 Black Meadow Road Chester, NY MLS# 1002697
        1 of 18
        $399,000
        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 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 260 Gibson Hill Road Chester, NY MLS# 1044316
              Save 260 Gibson Hill Road Chester, NY MLS# 1044316
              1 of 22
              $374,900
              3

              Beds

              1.1

              Baths

              1,644

              Sq.Ft.

              260 Gibson Hill Road

              Chester, NY

              Courtesy of KELLER WILLIAMS REALTY
              View 4704 Whispering Hills Chester, NY MLS# 1038636
                Save 4704 Whispering Hills Chester, NY MLS# 1038636
                1 of 19
                $370,000
                3

                Beds

                2.1

                Baths

                1,331

                Sq.Ft.

                4704 Whispering Hills

                Chester, NY

                Courtesy of SAHAGIAN REALTY LLC
                View 3211 Whispering Hills Chester, NY MLS# 1046996
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                1 of 40
                $370,000
                3

                Beds

                2.0

                Baths

                1,316

                Sq.Ft.

                3211 Whispering Hills

                Chester, NY

                Courtesy of RE/MAX BENCHMARK REALTY GROUP
                View 2921 Whispering Hills Chester, NY MLS# 1043986
                  Save 2921 Whispering Hills Chester, NY MLS# 1043986
                  1 of 42
                  $364,900
                  3

                  Beds

                  2.1

                  Baths

                  1,331

                  Sq.Ft.

                  2921 Whispering Hills

                  Chester, NY

                  Courtesy of ARC REALTY 1 IN SALES
                  View 3409 Whispering Hills Chester, NY MLS# 1032618
                    Save 3409 Whispering Hills Chester, NY MLS# 1032618
                    1 of 24
                    $360,000
                    3

                    Beds

                    2.1

                    Baths

                    1,331

                    Sq.Ft.

                    3409 Whispering Hills

                    Chester, NY

                    Courtesy of HOWARD HANNA RAND REALTY
                    View 2522 Whispering Hills Chester, NY MLS# 1027103
                      Save 2522 Whispering Hills Chester, NY MLS# 1027103
                      1 of 35
                      $355,000
                      3

                      Beds

                      2.1

                      Baths

                      1,331

                      Sq.Ft.

                      2522 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
                        0.0

                        Baths

                        235,224

                        Sq.Ft.

                        2 Virginia Lane

                        Chester, NY

                        Courtesy of KELLER WILLIAMS REALTY
                        View 3414 Whispering Hills Chester, NY MLS# 974398
                        • Virtual Tour
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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 18 Schueler Road Chester, NY MLS# 1046033
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                        1 of 43
                        $339,900
                        2

                        Beds

                        1.0

                        Baths

                        960

                        Sq.Ft.

                        18 Schueler Road

                        Chester, NY

                        Courtesy of Weichert Realtors - Monroe
                        View 3706 Whispering Hills Chester, NY MLS# 1039289
                        • Recently Listed
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                        1 of 18
                        $339,900
                        2

                        Beds

                        1.1

                        Baths

                        1,086

                        Sq.Ft.

                        3706 Whispering Hills

                        Chester, NY

                        Courtesy of EXP 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 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
                                0.0

                                Baths

                                248,292

                                Sq.Ft.

                                552 Pine Hill Road

                                Chester, NY

                                Courtesy of EREALTY ADVISORS, INC

                                About Chester

                                Listings in Chester, NY

                                108

                                Estimated median home price

                                $672,000
                                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 - 300K13
                                $300K - 400K18
                                $400K - 500K11
                                $500K - 600K7
                                $600K - 700K12
                                $700K - 800K18
                                $800K - 900K10
                                $900K - 1M6
                                $1M - Max12

                                Homes for Sale by Type in Chester, NY

                                Property TypeCount
                                Single Family73
                                Townhouse0
                                Condo21
                                Commercial7
                                Rental27
                                Lots and Land4
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family3
                                Mobile Home0
                                Farms0

                                (Data as of 10/14/2026)

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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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