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
        • Recently Listed
        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 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
              Save 2722 Whispering Hills Chester, NY MLS# 994269
              1 of 18
              $425,000
              3

              Beds

              2.1

              Baths

              1,331

              Sq.Ft.

              2722 Whispering Hills

              Chester, NY

              Courtesy of ARTISAN REALTY
              View 11 Oxford Depot Chester, NY MLS# 1002651
              • Recently Listed
              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 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
                • Recently Listed
                Save 492 Black Meadow Road Chester, NY MLS# 1002697
                1 of 17
                $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
                  • 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

                  About Chester

                  Listings in Chester, NY

                  85

                  Estimated median home price

                  $640,000
                  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 - 400K17
                  $400K - 500K11
                  $500K - 600K4
                  $600K - 700K8
                  $700K - 800K11
                  $800K - 900K10
                  $900K - 1M5
                  $1M - Max11

                  Homes for Sale by Type in Chester, NY

                  Property TypeCount
                  Single Family55
                  Townhouse0
                  Condo13
                  Commercial5
                  Rental25
                  Lots and Land12
                  Condo/Town/CoOp0
                  CoOp0
                  Multi Family0
                  Mobile Home0
                  Farms0

                  (Data as of 5/21/2026)

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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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