View 5 N Hudson Street Chester, NY MLS# 976521
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    1 of 28
    $500,000
    3

    Beds

    2.0

    Baths

    2,688

    Sq.Ft.

    5 N Hudson Street

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 37 Surrey Road Chester, NY MLS# 1007164
    • Recently Listed with Virtual Tour
    Save 37 Surrey Road Chester, NY MLS# 1007164
    1 of 40
    $500,000
    4

    Beds

    2.0

    Baths

    1,730

    Sq.Ft.

    37 Surrey Road

    Chester, NY

    Courtesy of EXP REALTY
    View 4 Oak Street Chester, NY MLS# 973625
      Save 4 Oak Street Chester, NY MLS# 973625
      1 of 42
      $499,900
      3

      Beds

      2.1

      Baths

      1,888

      Sq.Ft.

      4 Oak Street

      Chester, NY

      Courtesy of CRONIN & COMPANY REAL ESTATE
      The time to sell is now! THE TIME TO SELL IS NOW!
      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 1 N Hudson Street Chester, NY MLS# 1001003
          Save 1 N Hudson Street Chester, NY MLS# 1001003
          1 of 38
          $499,900
          3

          Beds

          2.0

          Baths

          1,778

          Sq.Ft.

          1 N Hudson Street

          Chester, NY

          Courtesy of KELLER WILLIAMS HUDSON VALLEY
          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 1367 Kings Highway Chester, NY MLS# 951876
              Save 1367 Kings Highway Chester, NY MLS# 951876
              1 of 13
              $460,000
              3

              Beds

              1.1

              Baths

              1,728

              Sq.Ft.

              1367 Kings Highway

              Chester, NY

              Courtesy of KARTEN REAL ESTATE SVCS LLC
              View 5 Roggia Road Chester, NY MLS# 978824
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              1 of 32
              $450,000
              3

              Beds

              2.0

              Baths

              1,882

              Sq.Ft.

              5 Roggia Road

              Chester, NY

              Courtesy of NAZMA REAL ESTATE LLC
              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 11 Oxford Depot Chester, NY MLS# 1002651
                    Save 11 Oxford Depot Chester, NY MLS# 1002651
                    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 2722 Whispering Hills Chester, NY MLS# 994269
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                    1 of 37
                    $424,999
                    3

                    Beds

                    2.1

                    Baths

                    1,331

                    Sq.Ft.

                    2722 Whispering Hills

                    Chester, NY

                    Courtesy of ARTISAN REALTY
                    View 7 Hambletonian Avenue Chester, NY MLS# 964090
                      Save 7 Hambletonian Avenue Chester, NY MLS# 964090
                      1 of 26
                      $399,900
                      2

                      Beds

                      1.0

                      Baths

                      1,026

                      Sq.Ft.

                      7 Hambletonian Avenue

                      Chester, NY

                      Courtesy of HOMESMART HOMES & ESTATES
                      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 4116 Whispering Hills Chester, NY MLS# 975277
                          Save 4116 Whispering Hills Chester, NY MLS# 975277
                          1 of 25
                          $375,000
                          3

                          Beds

                          2.1

                          Baths

                          1,355

                          Sq.Ft.

                          4116 Whispering Hills

                          Chester, NY

                          Courtesy of WILLIAM RAVEIS-NEW YORK, LLC
                          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 3910 Whispering Hills Chester, NY MLS# 946789
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                            1 of 11
                            $369,900
                            3

                            Beds

                            2.1

                            Baths

                            1,331

                            Sq.Ft.

                            3910 Whispering Hills

                            Chester, NY

                            Courtesy of EXP 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 Odyssey Drive Chester, NY MLS# 858370
                                Save Odyssey Drive Chester, NY MLS# 858370
                                1 of 4
                                $350,000
                                Studio

                                Beds

                                0.0

                                Baths

                                222,156

                                Sq.Ft.

                                Odyssey Drive

                                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

                                  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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