View 66 Whitetail Run Chester, NY MLS# 1033721
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    1 of 50
    $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
      Save TBD Rt-17M Chester, NY MLS# 1059544
      1 of 2
      $399,999
      30,000

      Sq.Ft.

      TBD Rt-17M

      Chester, NY

      Courtesy of EREALTY ADVISORS, INC
      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
        The time to sell is now! THE TIME TO SELL IS NOW!
        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 90 Odyssey Drive Chester, NY MLS# 1067328
            • Recently Listed
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            1 of 19
            $365,000
            0.0

            Baths

            222,156

            Sq.Ft.

            90 Odyssey Drive

            Chester, NY

            Courtesy of RE/MAX TOWN & COUNTRY
            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 2921 Whispering Hills Chester, NY MLS# 1043986
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                  1 of 42
                  $354,900
                  3

                  Beds

                  2.1

                  Baths

                  1,331

                  Sq.Ft.

                  2921 Whispering Hills

                  Chester, NY

                  Courtesy of ARC REALTY 1 IN SALES
                  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
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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 492 Black Meadow Road Chester, NY MLS# 1002697
                      Save 492 Black Meadow Road Chester, NY MLS# 1002697
                      1 of 18
                      $349,000
                      0.0

                      Baths

                      2,003,760

                      Sq.Ft.

                      492 Black Meadow Road

                      Chester, NY

                      Courtesy of EXP REALTY
                      View 18 Schueler Road Chester, NY MLS# 1046033
                      • Virtual Tour
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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
                        Save 3706 Whispering Hills Chester, NY MLS# 1039289
                        1 of 18
                        $339,900
                        2

                        Beds

                        1.1

                        Baths

                        1,086

                        Sq.Ft.

                        3706 Whispering Hills

                        Chester, NY

                        Courtesy of EXP REALTY
                        View 4108 Whispering Hills Chester, NY MLS# 1069532
                          Save 4108 Whispering Hills Chester, NY MLS# 1069532
                          1 of 1
                          $325,900
                          2

                          Beds

                          1.1

                          Baths

                          1,072

                          Sq.Ft.

                          4108 Whispering Hills

                          Chester, NY

                          Courtesy of KELLER WILLIAMS REALTY
                          View 14 School Street Chester, NY MLS# 1069090
                            Save 14 School Street Chester, NY MLS# 1069090
                            1 of 1
                            $299,999
                            3

                            Beds

                            1.0

                            Baths

                            1,046

                            Sq.Ft.

                            14 School Street

                            Chester, NY

                            Courtesy of HOWARD HANNA RAND REALTY
                            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
                              View 151 Main Street Chester, NY MLS# 1031155
                                Save 151 Main Street Chester, NY MLS# 1031155
                                1 of 17
                                $299,000
                                4

                                Beds

                                1.0

                                Baths

                                1,504

                                Sq.Ft.

                                151 Main Street

                                Chester, NY

                                Courtesy of HUDSON VALLEY GRIFFITH
                                View 2107 Whispering Hills Chester, NY MLS# 1050213
                                  Save 2107 Whispering Hills Chester, NY MLS# 1050213
                                  1 of 34
                                  $299,000
                                  2

                                  Beds

                                  1.1

                                  Baths

                                  1,086

                                  Sq.Ft.

                                  2107 Whispering Hills

                                  Chester, NY

                                  Courtesy of WANSOR REALTY

                                  About Chester

                                  Listings in Chester, NY

                                  97

                                  Estimated median home price

                                  $690,000
                                  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 - 300K11
                                  $300K - 400K15
                                  $400K - 500K10
                                  $500K - 600K7
                                  $600K - 700K7
                                  $700K - 800K17
                                  $800K - 900K12
                                  $900K - 1M8
                                  $1M - Max9

                                  Homes for Sale by Type in Chester, NY

                                  Property TypeCount
                                  Single Family69
                                  Townhouse0
                                  Condo14
                                  Commercial7
                                  Rental30
                                  Lots and Land4
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family3
                                  Mobile Home0
                                  Farms0

                                  (Data as of 11/5/2026)

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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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