View 558 Pine Hill Road Chester, NY MLS# 958731
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    $799,000
    4

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    2.1

    Baths

    3,120

    Sq.Ft.

    558 Pine Hill Road

    Chester, NY

    Courtesy of EREALTY ADVISORS, INC
    View 552 Pine Hill Road Chester, NY MLS# 958740
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      $299,000
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      0.0

      Baths

      248,292

      Sq.Ft.

      552 Pine Hill Road

      Chester, NY

      Courtesy of EREALTY ADVISORS, INC
      View 1005 Whispering Hills Chester, NY MLS# 964957
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        $249,900
        2

        Beds

        1.1

        Baths

        1,053

        Sq.Ft.

        1005 Whispering Hills

        Chester, NY

        Courtesy of ARC REALTY 1 IN SALES
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 7 Hambletonian Avenue Chester, NY MLS# 964090
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          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 2 Imperial Park Chester, NY MLS# 964115
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            $149,900
            Studio

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            0.0

            Baths

            8,875

            Sq.Ft.

            2 Imperial Park

            Chester, NY

            Courtesy of HOMESMART HOMES & ESTATES
            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 2913 Whispering Hills Chester, NY MLS# 962709
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              1 of 29
              $279,900
              2

              Beds

              1.0

              Baths

              1,084

              Sq.Ft.

              2913 Whispering Hills

              Chester, NY

              Courtesy of HOMESMART HOMES & ESTATES
              View 4 Debbie Court Chester, NY MLS# 962813
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                $840,000
                5

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                5.1

                Baths

                5,403

                Sq.Ft.

                4 Debbie Court

                Chester, NY

                Courtesy of FLAG REALTY GROUP
                View 487 Black Meadow Road Chester, NY MLS# 960665
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                  1 of 47
                  $725,000
                  6

                  Beds

                  3.1

                  Baths

                  4,204

                  Sq.Ft.

                  487 Black Meadow Road

                  Chester, NY

                  Courtesy of JOSEPH BARATTA COMPANY REALTY
                  View 5 Bens Way Chester, NY MLS# 959390
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                    OPEN HOUSE: Saturday 4/18 12:00 PM - 2:00 PM
                    $699,999
                    4

                    Beds

                    2.1

                    Baths

                    2,544

                    Sq.Ft.

                    5 Bens Way

                    Chester, NY

                    Courtesy of KELLER WILLIAMS HUDSON VALLEY
                    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 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
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                        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
                          $675,000
                          Studio

                          Beds

                          0.0

                          Baths

                          87,120

                          Sq.Ft.

                          50 Elkay Drive

                          Chester, NY

                          Courtesy of POINT REALTY USA
                          View 1367 Kings Highway Chester, NY MLS# 951876
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                            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 12 Damian Court Chester, NY MLS# 950640
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                              1 of 34
                              $999,000
                              5

                              Beds

                              4.0

                              Baths

                              3,136

                              Sq.Ft.

                              12 Damian Court

                              Chester, NY

                              Courtesy of MS REALTY GROUP USA, INC
                              View 4508 Whispering Hills Chester, NY MLS# 951306
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                                1 of 20
                                $299,999
                                2

                                Beds

                                1.1

                                Baths

                                1,072

                                Sq.Ft.

                                4508 Whispering Hills

                                Chester, NY

                                Courtesy of EXP REALTY
                                View 2113 Whispering Hills Chester, NY MLS# 950534
                                  Save 2113 Whispering Hills Chester, NY MLS# 950534
                                  1 of 24
                                  $275,000
                                  2

                                  Beds

                                  1.0

                                  Baths

                                  1,084

                                  Sq.Ft.

                                  2113 Whispering Hills

                                  Chester, NY

                                  Courtesy of KELLER WILLIAMS REALTY
                                  View 3910 Whispering Hills Chester, NY MLS# 946789
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                                  1 of 9
                                  $369,900
                                  3

                                  Beds

                                  2.1

                                  Baths

                                  1,331

                                  Sq.Ft.

                                  3910 Whispering Hills

                                  Chester, NY

                                  Courtesy of EXP REALTY
                                  View 2 Garnett Hill Road Chester, NY MLS# 931380
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                                  1 of 27
                                  $999,999
                                  5

                                  Beds

                                  2.1

                                  Baths

                                  4,772

                                  Sq.Ft.

                                  2 Garnett Hill Road

                                  Chester, NY

                                  Courtesy of PLATINUM REALTY ASSOCIATES
                                  View Oxford Road Chester, NY MLS# 946546
                                    Save Oxford Road Chester, NY MLS# 946546
                                    1 of 2
                                    $199,000
                                    Studio

                                    Beds

                                    0.0

                                    Baths

                                    313,632

                                    Sq.Ft.

                                    Oxford Road

                                    Chester, NY

                                    Courtesy of BLOOMING REALTY

                                    About Chester

                                    Listings in Chester, NY

                                    66

                                    Estimated median home price

                                    $612,000
                                    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 - 300K7
                                    $300K - 400K14
                                    $400K - 500K8
                                    $500K - 600K1
                                    $600K - 700K7
                                    $700K - 800K8
                                    $800K - 900K6
                                    $900K - 1M4
                                    $1M - Max8

                                    Homes for Sale by Type in Chester, NY

                                    Property TypeCount
                                    Single Family37
                                    Townhouse0
                                    Condo12
                                    Commercial5
                                    Rental24
                                    Lots and Land12
                                    Condo/Town/CoOp0
                                    CoOp0
                                    Multi Family0
                                    Mobile Home0
                                    Farms0

                                    (Data as of 4/13/2026)

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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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