View Main Street Chester, NY MLS# H6204360
    Save Main Street Chester, NY MLS# H6204360
    1 of 2
    $500,000
    Studio

    Beds

    0.0

    Baths

    36,098

    Sq.Ft.

    Main Street

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 5 N Hudson Street Chester, NY MLS# 976521
      Save 5 N Hudson Street Chester, NY MLS# 976521
      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 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 1 N Hudson Street Chester, NY MLS# 1001003
          Save 1 N Hudson Street Chester, NY MLS# 1001003
          1 of 38
          OPEN HOUSE: Saturday 5/23 11:00 AM - 1:00 PM
          $499,900
          3

          Beds

          2.0

          Baths

          1,778

          Sq.Ft.

          1 N Hudson Street

          Chester, NY

          Courtesy of KELLER WILLIAMS HUDSON VALLEY
          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
            • Virtual Tour
            Save 5 Roggia Road Chester, NY MLS# 978824
            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
            • Recently Listed
            Save 151 Laroe Road Chester, NY MLS# 995916
            1 of 43
            $450,000
            3

            Beds

            1.1

            Baths

            1,177

            Sq.Ft.

            151 Laroe Road

            Chester, NY

            Courtesy of KELLER WILLIAMS REALTY
            View 31 Hudson Street Chester, NY MLS# 963657
              Save 31 Hudson Street Chester, NY MLS# 963657
              1 of 25
              $449,900
              2

              Beds

              2.0

              Baths

              1,998

              Sq.Ft.

              31 Hudson Street

              Chester, NY

              Courtesy of BHG REAL ESTATE GREEN TEAM
              View 71 Greycourt Road Chester, NY MLS# 942503
                Save 71 Greycourt Road Chester, NY MLS# 942503
                1 of 38
                $449,000
                3

                Beds

                1.1

                Baths

                1,056

                Sq.Ft.

                71 Greycourt Road

                Chester, NY

                Courtesy of BLOOMING 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 2722 Whispering Hills Chester, NY MLS# 994269
                  • Recently Listed
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                  1 of 18
                  $425,000
                  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 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
                      • Recently Listed
                      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
                      • Virtual Tour
                      Save 3910 Whispering Hills Chester, NY MLS# 946789
                      1 of 11
                      $369,900
                      3

                      Beds

                      2.1

                      Baths

                      1,331

                      Sq.Ft.

                      3910 Whispering Hills

                      Chester, NY

                      Courtesy of EXP REALTY
                      View 2203 Whispering Hills Chester, NY MLS# 954443
                        Save 2203 Whispering Hills Chester, NY MLS# 954443
                        1 of 24
                        $362,900
                        3

                        Beds

                        2.1

                        Baths

                        1,331

                        Sq.Ft.

                        2203 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 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
                              View 307 Gibson Hill Road Chester, NY MLS# 968972
                                Save 307 Gibson Hill Road Chester, NY MLS# 968972
                                1 of 38
                                $350,000
                                2

                                Beds

                                1.0

                                Baths

                                1,272

                                Sq.Ft.

                                307 Gibson Hill Road

                                Chester, NY

                                Courtesy of HOWARD HANNA RAND REALTY

                                About Chester

                                Listings in Chester, NY

                                84

                                Estimated median home price

                                $637,500
                                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 - 400K17
                                $400K - 500K11
                                $500K - 600K4
                                $600K - 700K7
                                $700K - 800K12
                                $800K - 900K9
                                $900K - 1M5
                                $1M - Max11

                                Homes for Sale by Type in Chester, NY

                                Property TypeCount
                                Single Family54
                                Townhouse0
                                Condo13
                                Commercial5
                                Rental27
                                Lots and Land12
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family0
                                Mobile Home0
                                Farms0

                                (Data as of 5/20/2026)

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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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