View 11 Oxford Depot Chester, NY MLS# 1002651
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    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 60 Whitetail Run Chester, NY MLS# 1002536
        Save 60 Whitetail Run Chester, NY MLS# 1002536
        1 of 7
        $900,000
        4

        Beds

        2.1

        Baths

        2,588

        Sq.Ft.

        60 Whitetail Run

        Chester, NY

        Courtesy of REALTY BLUE CORP
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 2722 Whispering Hills Chester, NY MLS# 994269
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        Save 2722 Whispering Hills Chester, NY MLS# 994269
        1 of 37
        $424,999
        3

        Beds

        2.1

        Baths

        1,331

        Sq.Ft.

        2722 Whispering Hills

        Chester, NY

        Courtesy of ARTISAN REALTY
        View 220 Oxford Road Chester, NY MLS# 000137
          Save 220 Oxford Road Chester, NY MLS# 000137
          1 of 3
          $899,000
          3

          Beds

          3.1

          Baths

          3,535

          Sq.Ft.

          220 Oxford Road

          Chester, NY

          Courtesy of BLOOMING REALTY
          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 4 Debbie Court Chester, NY MLS# 995223
              Save 4 Debbie Court Chester, NY MLS# 995223
              1 of 49
              OPEN HOUSE: Sunday 6/14 1:15 PM - 2:00 PM
              $785,000
              5

              Beds

              5.1

              Baths

              5,403

              Sq.Ft.

              4 Debbie Court

              Chester, NY

              Courtesy of FLAG REALTY GROUP
              View 2 Garnett Hill Road Chester, NY MLS# 999261
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              1 of 35
              $999,999
              5

              Beds

              2.1

              Baths

              4,772

              Sq.Ft.

              2 Garnett Hill Road

              Chester, NY

              Courtesy of PLATINUM REALTY ASSOCIATES
              View 63 Hubshop Road Chester, NY MLS# 997559
                Save 63 Hubshop Road Chester, NY MLS# 997559
                1 of 45
                $499,000
                4

                Beds

                2.1

                Baths

                2,060

                Sq.Ft.

                63 Hubshop Road

                Chester, NY

                Courtesy of KELLER WILLIAMS REALTY
                View 58 Nancy Lane Chester, NY MLS# 995624
                  Save 58 Nancy Lane Chester, NY MLS# 995624
                  1 of 49
                  $769,000
                  3

                  Beds

                  2.1

                  Baths

                  2,718

                  Sq.Ft.

                  58 Nancy Lane

                  Chester, NY

                  Courtesy of HOWARD HANNA RAND REALTY
                  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 19 High Street Chester, NY MLS# 995148
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                    $1,195,000
                    9

                    Beds

                    6.1

                    Baths

                    4,965

                    Sq.Ft.

                    19 High Street

                    Chester, NY

                    Courtesy of KELLER WILLIAMS REALTY
                    View 4 Greycourt Road Chester, NY MLS# 992700
                      Save 4 Greycourt Road Chester, NY MLS# 992700
                      1 of 12
                      $640,000
                      3

                      Beds

                      1.1

                      Baths

                      2,136

                      Sq.Ft.

                      4 Greycourt Road

                      Chester, NY

                      Courtesy of MK REALTY INC
                      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 19 Greentree Lane Chester, NY MLS# 988789
                          Save 19 Greentree Lane Chester, NY MLS# 988789
                          1 of 50
                          $3,400,000
                          4

                          Beds

                          4.0

                          Baths

                          7,750

                          Sq.Ft.

                          19 Greentree Lane

                          Chester, NY

                          Courtesy of SERHANT LLC
                          View 2 Heidi Lane Chester, NY MLS# 988299
                            Save 2 Heidi Lane Chester, NY MLS# 988299
                            1 of 44
                            $899,900
                            5

                            Beds

                            3.0

                            Baths

                            3,846

                            Sq.Ft.

                            2 Heidi Lane

                            Chester, NY

                            Courtesy of CRONIN & COMPANY REAL ESTATE
                            View 2 Primrose Lane Chester, NY MLS# 991517
                              Save 2 Primrose Lane Chester, NY MLS# 991517
                              1 of 42
                              $849,900
                              4

                              Beds

                              3.0

                              Baths

                              2,370

                              Sq.Ft.

                              2 Primrose Lane

                              Chester, NY

                              Courtesy of Weichert Realtors - Monroe
                              View 35 Maple Avenue Chester, NY MLS# 990509
                                Save 35 Maple Avenue Chester, NY MLS# 990509
                                1 of 29
                                $499,900
                                3

                                Beds

                                3.0

                                Baths

                                2,032

                                Sq.Ft.

                                35 Maple Avenue

                                Chester, NY

                                Courtesy of RE/MAX BENCHMARK REALTY GROUP
                                View 2323 Whispering Hills Chester, NY MLS# 979690
                                  Save 2323 Whispering Hills Chester, NY MLS# 979690
                                  1 of 38
                                  $327,000
                                  2

                                  Beds

                                  2.0

                                  Baths

                                  1,316

                                  Sq.Ft.

                                  2323 Whispering Hills

                                  Chester, NY

                                  Courtesy of CENTURY 21 FULL SERVICE REALTY
                                  View 149 Creamery Pond Road Chester, NY MLS# 986323
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                                  1 of 50
                                  OPEN HOUSE: Sunday 6/14 12:00 PM - 3:00 PM
                                  $849,900
                                  3

                                  Beds

                                  3.0

                                  Baths

                                  2,740

                                  Sq.Ft.

                                  149 Creamery Pond Road

                                  Chester, NY

                                  Courtesy of KELLER WILLIAMS REALTY

                                  About Chester

                                  Listings in Chester, NY

                                  95

                                  Estimated median home price

                                  $675,000
                                  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 - 100K0
                                  $100K - 200K3
                                  $200K - 300K5
                                  $300K - 400K14
                                  $400K - 500K14
                                  $500K - 600K7
                                  $600K - 700K6
                                  $700K - 800K11
                                  $800K - 900K12
                                  $900K - 1M7
                                  $1M - Max16

                                  Homes for Sale by Type in Chester, NY

                                  Property TypeCount
                                  Single Family65
                                  Townhouse0
                                  Condo10
                                  Commercial6
                                  Rental28
                                  Lots and Land13
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family1
                                  Mobile Home0
                                  Farms0

                                  (Data as of 6/14/2026)

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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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