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 3601 Whispering Hills 3601 Chester, NY MLS# 972345
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    1 of 42
    $305,000
    2

    Beds

    1.0

    Baths

    1,084

    Sq.Ft.

    3601 Whispering Hills 3601

    Chester, NY

    Courtesy of Weichert Realtors - Monroe
    View 55 Beverly Road Chester, NY MLS# 977281
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    Save 55 Beverly Road Chester, NY MLS# 977281
    1 of 49
    $735,000
    4

    Beds

    3.1

    Baths

    3,356

    Sq.Ft.

    55 Beverly Road

    Chester, NY

    Courtesy of HOWARD HANNA RAND REALTY
    The time to sell is now! THE TIME TO SELL IS NOW!
    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 21 Bull Mine Road Chester, NY MLS# 973228
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      1 of 48
      $925,000
      5

      Beds

      3.1

      Baths

      3,680

      Sq.Ft.

      21 Bull Mine Road

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View Address not provided Chester, NY MLS# 962912
        Save Address not provided Chester, NY MLS# 962912
        1 of 1
        $1,000,000

        Address not provided

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        View 307 Gibson Hill Road Chester, NY MLS# 968972
          Save 307 Gibson Hill Road Chester, NY MLS# 968972
          1 of 38
          $350,000
          2

          Beds

          1.0

          Baths

          1,272

          Sq.Ft.

          307 Gibson Hill Road

          Chester, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 2203 Whispering Hills Chester, NY MLS# 954443
            Save 2203 Whispering Hills Chester, NY MLS# 954443
            1 of 24
            $362,900
            3

            Beds

            2.1

            Baths

            1,331

            Sq.Ft.

            2203 Whispering Hills

            Chester, NY

            Courtesy of HOWARD HANNA RAND REALTY
            View 1414 Kings Highway Chester, NY MLS# 965992
              Save 1414 Kings Highway Chester, NY MLS# 965992
              1 of 9
              $879,900
              4

              Beds

              2.1

              Baths

              3,200

              Sq.Ft.

              1414 Kings Highway

              Chester, NY

              Courtesy of KELLER WILLIAMS REALTY
              View 10 Wells Sweep Lane Chester, NY MLS# 966048
                Save 10 Wells Sweep Lane Chester, NY MLS# 966048
                1 of 8
                $869,900
                4

                Beds

                2.1

                Baths

                3,000

                Sq.Ft.

                10 Wells Sweep Lane

                Chester, NY

                Courtesy of KELLER WILLIAMS REALTY
                View 558 Pine Hill Road Chester, NY MLS# 958731
                  Save 558 Pine Hill Road Chester, NY MLS# 958731
                  1 of 46
                  $699,000
                  4

                  Beds

                  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
                    Save 552 Pine Hill Road Chester, NY MLS# 958740
                    1 of 1
                    $299,000
                    Studio

                    Beds

                    0.0

                    Baths

                    248,292

                    Sq.Ft.

                    552 Pine Hill Road

                    Chester, NY

                    Courtesy of EREALTY ADVISORS, INC
                    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 2 Imperial Park Chester, NY MLS# 964115
                        Save 2 Imperial Park Chester, NY MLS# 964115
                        1 of 9
                        $149,900
                        Studio

                        Beds

                        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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                        1 of 42
                        $699,000
                        4

                        Beds

                        2.1

                        Baths

                        2,506

                        Sq.Ft.

                        34 Booth Road

                        Chester, NY

                        Courtesy of CENTURY 21 FULL SERVICE REALTY
                        View 20 Goshen Road Chester, NY MLS# 961236
                          Save 20 Goshen Road Chester, NY MLS# 961236
                          1 of 50
                          $1,725,000
                          4

                          Beds

                          2.1

                          Baths

                          3,348

                          Sq.Ft.

                          20 Goshen Road

                          Chester, NY

                          Courtesy of EXP REALTY
                          View 487 Black Meadow Road Chester, NY MLS# 960665
                            Save 487 Black Meadow Road Chester, NY MLS# 960665
                            1 of 50
                            $725,000
                            6

                            Beds

                            3.1

                            Baths

                            4,204

                            Sq.Ft.

                            487 Black Meadow Road

                            Chester, NY

                            Courtesy of JOSEPH BARATTA COMPANY REALTY
                            View 34 Mountainside Drive Chester, NY MLS# 956879
                              Save 34 Mountainside Drive Chester, NY MLS# 956879
                              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
                                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

                                  About Chester

                                  Listings in Chester, NY

                                  88

                                  Estimated median home price

                                  $637,500
                                  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 - 400K18
                                  $400K - 500K11
                                  $500K - 600K5
                                  $600K - 700K7
                                  $700K - 800K12
                                  $800K - 900K10
                                  $900K - 1M6
                                  $1M - Max11

                                  Homes for Sale by Type in Chester, NY

                                  Property TypeCount
                                  Single Family57
                                  Townhouse0
                                  Condo13
                                  Commercial5
                                  Rental24
                                  Lots and Land13
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family0
                                  Mobile Home0
                                  Farms0

                                  (Data as of 5/27/2026)

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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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