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
    View 50 Elkay Drive Chester, NY MLS# 954329
      Save 50 Elkay Drive Chester, NY MLS# 954329
      1 of 3
      $625,000
      Studio

      Beds

      0.0

      Baths

      87,120

      Sq.Ft.

      50 Elkay Drive

      Chester, NY

      Courtesy of POINT REALTY USA
      View 17 Woodridge Drive Chester, NY MLS# 972648
        Save 17 Woodridge Drive Chester, NY MLS# 972648
        1 of 50
        $624,900
        4

        Beds

        2.1

        Baths

        2,524

        Sq.Ft.

        17 Woodridge Drive

        Chester, NY

        Courtesy of EXP REALTY
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 558 Pine Hill Road Chester, NY MLS# 958731
          Save 558 Pine Hill Road Chester, NY MLS# 958731
          1 of 50
          $599,000
          4

          Beds

          2.1

          Baths

          3,120

          Sq.Ft.

          558 Pine Hill Road

          Chester, NY

          Courtesy of EREALTY ADVISORS, INC
          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 24 Walnut Street Chester, NY MLS# 1004369
            • Recently Listed
            Save 24 Walnut Street Chester, NY MLS# 1004369
            1 of 28
            $579,999
            4

            Beds

            2.1

            Baths

            2,698

            Sq.Ft.

            24 Walnut Street

            Chester, NY

            Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
            View 94 Booth Road Chester, NY MLS# 898870
            • Recently Listed
            Save 94 Booth Road Chester, NY MLS# 898870
            1 of 21
            $550,000
            3

            Beds

            2.1

            Baths

            2,083

            Sq.Ft.

            94 Booth Road

            Chester, NY

            Courtesy of COMPASS GREATER NY, LLC
            View 107 Pine Hill Road Chester, NY MLS# 1003546
            • Recently Listed
            Save 107 Pine Hill Road Chester, NY MLS# 1003546
            1 of 33
            $549,000
            3

            Beds

            2.1

            Baths

            1,730

            Sq.Ft.

            107 Pine Hill Road

            Chester, NY

            Courtesy of HUDSON VALLEY GRIFFITH
            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 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
                  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 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

                      About Chester

                      Listings in Chester, NY

                      87

                      Estimated median home price

                      $635,000
                      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 - 500K13
                      $500K - 600K5
                      $600K - 700K5
                      $700K - 800K12
                      $800K - 900K11
                      $900K - 1M5
                      $1M - Max13

                      Homes for Sale by Type in Chester, NY

                      Property TypeCount
                      Single Family57
                      Townhouse0
                      Condo11
                      Commercial5
                      Rental27
                      Lots and Land13
                      Condo/Town/CoOp0
                      CoOp0
                      Multi Family1
                      Mobile Home0
                      Farms0

                      (Data as of 6/7/2026)

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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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