View 558 Pine Hill Road Chester, NY MLS# 958731
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    1 of 50
    OPEN HOUSE: Sunday 6/14 1:00 PM - 2:00 PM
    $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
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      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
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 94 Booth Road Chester, NY MLS# 898870
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      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 3318 State Route 94 Chester, NY MLS# 1008703
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      1 of 28
      $549,900
      3

      Beds

      2.0

      Baths

      2,138

      Sq.Ft.

      3318 State Route 94

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 107 Pine Hill Road Chester, NY MLS# 1003546
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      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 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
                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 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 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
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                        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
                          • Recently Listed
                          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

                          About Chester

                          Listings in Chester, NY

                          90

                          Estimated median home price

                          $669,995
                          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 - 500K12
                          $500K - 600K6
                          $600K - 700K5
                          $700K - 800K12
                          $800K - 900K11
                          $900K - 1M7
                          $1M - Max14

                          Homes for Sale by Type in Chester, NY

                          Property TypeCount
                          Single Family60
                          Townhouse0
                          Condo11
                          Commercial5
                          Rental27
                          Lots and Land13
                          Condo/Town/CoOp0
                          CoOp0
                          Multi Family1
                          Mobile Home0
                          Farms0

                          (Data as of 6/10/2026)

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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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