View 50 Elkay Drive Chester, NY MLS# 954329
    Save 50 Elkay Drive Chester, NY MLS# 954329
    1 of 3
    $650,000
    Studio

    Beds

    0.0

    Baths

    87,120

    Sq.Ft.

    50 Elkay Drive

    Chester, NY

    Courtesy of POINT REALTY USA
    View 4 Greycourt Road Chester, NY MLS# 992700
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    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 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
      Save 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
      1 of 38
      $635,000
      3

      Beds

      2.1

      Baths

      1,954

      Sq.Ft.

      25 Sugarloaf Mountain Road

      Chester, NY

      Courtesy of CRONIN & COMPANY REAL ESTATE
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 101 Whitetail Run Chester, NY MLS# 983196
        Save 101 Whitetail Run Chester, NY MLS# 983196
        1 of 35
        $589,000
        3

        Beds

        2.1

        Baths

        1,854

        Sq.Ft.

        101 Whitetail Run

        Chester, NY

        Courtesy of CRONIN & COMPANY REAL ESTATE
        View 208 Glenmere Road Chester, NY MLS# 996648
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        Save 208 Glenmere Road Chester, NY MLS# 996648
        1 of 30
        $550,000
        5

        Beds

        2.1

        Baths

        1,815

        Sq.Ft.

        208 Glenmere Road

        Chester, NY

        Courtesy of MK REALTY INC
        View 35 Maple Avenue Chester, NY MLS# 990509
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        Save 35 Maple Avenue Chester, NY MLS# 990509
        1 of 29
        OPEN HOUSE: Sunday 5/17 1:00 PM - 3:00 PM
        $529,900
        3

        Beds

        3.0

        Baths

        2,032

        Sq.Ft.

        35 Maple Avenue

        Chester, NY

        Courtesy of RE/MAX BENCHMARK REALTY GROUP
        View 63 Hubshop Road Chester, NY MLS# 997559
        • Recently Listed
        Save 63 Hubshop Road Chester, NY MLS# 997559
        1 of 45
        OPEN HOUSE: Saturday 5/16 11:00 AM - 1:00 PM
        $529,000
        4

        Beds

        2.1

        Baths

        2,060

        Sq.Ft.

        63 Hubshop Road

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        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
              View 11 Oxford Depot Chester, NY MLS# 991245
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              1 of 27
              OPEN HOUSE: Saturday 5/16 12:00 PM - 2:00 PM
              $499,900
              3

              Beds

              2.0

              Baths

              1,748

              Sq.Ft.

              11 Oxford Depot

              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
                • Virtual Tour
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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
                • 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 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
                      Save 2722 Whispering Hills Chester, NY MLS# 994269
                      1 of 1
                      OPEN HOUSE: Sunday 5/17 12:00 PM - 2:00 PM
                      $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 23
                        $410,000
                        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 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

                          About Chester

                          Listings in Chester, NY

                          79

                          Estimated median home price

                          $650,000
                          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 - 400K15
                          $400K - 500K10
                          $500K - 600K4
                          $600K - 700K7
                          $700K - 800K12
                          $800K - 900K8
                          $900K - 1M4
                          $1M - Max11

                          Homes for Sale by Type in Chester, NY

                          Property TypeCount
                          Single Family50
                          Townhouse0
                          Condo12
                          Commercial5
                          Rental27
                          Lots and Land12
                          Condo/Town/CoOp0
                          CoOp0
                          Multi Family0
                          Mobile Home0
                          Farms0

                          (Data as of 5/13/2026)

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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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