View 3910 Whispering Hills Chester, NY MLS# 946789
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$369,900
3

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3910 Whispering Hills

Chester, NY

Courtesy of EXP REALTY
View 4116 Whispering Hills Chester, NY MLS# 975277
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    $375,000
    3

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    2.1

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    1,355

    Sq.Ft.

    4116 Whispering Hills

    Chester, NY

    Courtesy of WILLIAM RAVEIS-NEW YORK, LLC
    View 7 Hambletonian Avenue Chester, NY MLS# 964090
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      1 of 23
      $410,000
      2

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      1.0

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      1,026

      Sq.Ft.

      7 Hambletonian Avenue

      Chester, NY

      Courtesy of HOMESMART HOMES & ESTATES
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 16 Oakland Avenue Chester, NY MLS# 939522
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        1 of 49
        $425,000
        4

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        2.1

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        2,090

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        16 Oakland Avenue

        Chester, NY

        Courtesy of BHG REAL ESTATE GREEN TEAM
        View 31 Hudson Street Chester, NY MLS# 963657
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          $449,900
          2

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          2.0

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          1,998

          Sq.Ft.

          31 Hudson Street

          Chester, NY

          Courtesy of BHG REAL ESTATE GREEN TEAM
          View 5 Roggia Road Chester, NY MLS# 978824
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          $450,000
          3

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          2.0

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          1,882

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          5 Roggia Road

          Chester, NY

          Courtesy of NAZMA REAL ESTATE LLC
          View 1367 Kings Highway Chester, NY MLS# 951876
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            1 of 13
            $460,000
            3

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            1.1

            Baths

            1,728

            Sq.Ft.

            1367 Kings Highway

            Chester, NY

            Courtesy of KARTEN REAL ESTATE SVCS LLC
            View Main Street Chester, NY MLS# H6204360
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              1 of 2
              $500,000
              Studio

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              0.0

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              36,098

              Sq.Ft.

              Main Street

              Chester, NY

              Courtesy of KELLER WILLIAMS REALTY
              View 5 N Hudson Street Chester, NY MLS# 976521
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                $500,000
                3

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                2.0

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                2,688

                Sq.Ft.

                5 N Hudson Street

                Chester, NY

                Courtesy of KELLER WILLIAMS REALTY
                View 11 Oxford Depot Chester, NY MLS# 991245
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                $519,000
                3

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                2.0

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                1,748

                Sq.Ft.

                11 Oxford Depot

                Chester, NY

                Courtesy of KELLER WILLIAMS REALTY
                View 35 Maple Avenue Chester, NY MLS# 990509
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                $549,900
                3

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                3.0

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                2,032

                Sq.Ft.

                35 Maple Avenue

                Chester, NY

                Courtesy of RE/MAX BENCHMARK REALTY GROUP
                View 101 Whitetail Run Chester, NY MLS# 983196
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                  1 of 35
                  $589,000
                  3

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                  2.1

                  Baths

                  1,854

                  Sq.Ft.

                  101 Whitetail Run

                  Chester, NY

                  Courtesy of CRONIN & COMPANY REAL ESTATE
                  View 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
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                    1 of 38
                    $635,000
                    3

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                    2.1

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                    1,954

                    Sq.Ft.

                    25 Sugarloaf Mountain Road

                    Chester, NY

                    Courtesy of CRONIN & COMPANY REAL ESTATE
                    View 101 Oxford Road Chester, NY MLS# 943068
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                    $639,000
                    3

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                    1.1

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                    1,816

                    Sq.Ft.

                    101 Oxford Road

                    Chester, NY

                    Courtesy of LOOP REALTY INC
                    View 50 Elkay Drive Chester, NY MLS# 954329
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                      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 360 Prospect Road Chester, NY MLS# 944607
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                        $689,000
                        3

                        Beds

                        3.0

                        Baths

                        3,000

                        Sq.Ft.

                        360 Prospect Road

                        Chester, NY

                        Courtesy of EREALTY ADVISORS, INC
                        View 34 Booth Road Chester, NY MLS# 961100
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                        $699,000
                        4

                        Beds

                        2.1

                        Baths

                        2,506

                        Sq.Ft.

                        34 Booth Road

                        Chester, NY

                        Courtesy of CENTURY 21 FULL SERVICE REALTY
                        View 558 Pine Hill Road Chester, NY MLS# 958731
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                          1 of 50
                          $699,000
                          4

                          Beds

                          2.1

                          Baths

                          3,120

                          Sq.Ft.

                          558 Pine Hill Road

                          Chester, NY

                          Courtesy of EREALTY ADVISORS, INC
                          View 34 Mountainside Drive Chester, NY MLS# 956879
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                            1 of 8
                            $699,990
                            4

                            Beds

                            3.0

                            Baths

                            1,867

                            Sq.Ft.

                            34 Mountainside Drive

                            Chester, NY

                            Courtesy of OUR HOUSE REAL ESTATE GROUP
                            View 5 Bens Way Chester, NY MLS# 959390
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                              1 of 26
                              OPEN HOUSE: Saturday 5/2 1:00 PM - 3:00 PM
                              $699,999
                              4

                              Beds

                              2.1

                              Baths

                              2,544

                              Sq.Ft.

                              5 Bens Way

                              Chester, NY

                              Courtesy of KELLER WILLIAMS HUDSON VALLEY

                              About Chester

                              Listings in Chester, NY

                              73

                              Estimated median home price

                              $699,000
                              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 - 400K14
                              $400K - 500K7
                              $500K - 600K2
                              $600K - 700K8
                              $700K - 800K11
                              $800K - 900K8
                              $900K - 1M4
                              $1M - Max11

                              Homes for Sale by Type in Chester, NY

                              Property TypeCount
                              Single Family44
                              Townhouse0
                              Condo11
                              Commercial5
                              Rental24
                              Lots and Land12
                              Condo/Town/CoOp0
                              CoOp0
                              Multi Family1
                              Mobile Home0
                              Farms0

                              (Data as of 5/1/2026)

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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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