View 63 Hubshop Road Chester, NY MLS# 1039933
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    1 of 19
    $459,000
    4

    Beds

    2.1

    Baths

    2,060

    Sq.Ft.

    63 Hubshop Road

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 32 Surrey Road Chester, NY MLS# 1040785
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      1 of 39
      $475,000
      4

      Beds

      1.1

      Baths

      1,820

      Sq.Ft.

      32 Surrey Road

      Chester, NY

      Courtesy of EXP REALTY
      View 8 Bridle Lane Chester, NY MLS# 1036394
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      1 of 45
      $495,000
      4

      Beds

      1.1

      Baths

      1,820

      Sq.Ft.

      8 Bridle Lane

      Chester, NY

      Courtesy of KELLER WILLIAMS REALTY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 1367 Kings Highway Chester, NY MLS# 1036770
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        1 of 16
        $440,000
        3

        Beds

        1.1

        Baths

        1,728

        Sq.Ft.

        1367 Kings Highway

        Chester, NY

        Courtesy of GREENE REALTY GROUP
        View 166 Bull Mill Road Chester, NY MLS# 1030923
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          1 of 37
          $289,000
          2

          Beds

          1.0

          Baths

          1,004

          Sq.Ft.

          166 Bull Mill Road

          Chester, NY

          Courtesy of KELLER WILLIAMS VALLEY REALTY
          View 412 Laroe Road Chester, NY MLS# 1035387
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          1 of 46
          OPEN HOUSE: Saturday 10/17 12:00 PM - 2:00 PM
          $605,000
          3

          Beds

          2.0

          Baths

          1,848

          Sq.Ft.

          412 Laroe Road

          Chester, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 21 Trotting Drive Chester, NY MLS# 1030740
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          1 of 49
          $475,000
          3

          Beds

          2.0

          Baths

          1,624

          Sq.Ft.

          21 Trotting Drive

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 70 Main Street Chester, NY MLS# 1034449
            Save 70 Main Street Chester, NY MLS# 1034449
            1 of 27
            $419,000
            3

            Beds

            1.2

            Baths

            1,357

            Sq.Ft.

            70 Main Street

            Chester, NY

            Courtesy of CURASI REALTY, INC.
            View 66 Whitetail Run Chester, NY MLS# 1033721
              Save 66 Whitetail Run Chester, NY MLS# 1033721
              1 of 50
              $435,000
              3

              Beds

              1.1

              Baths

              1,500

              Sq.Ft.

              66 Whitetail Run

              Chester, NY

              Courtesy of HOWARD HANNA RAND REALTY
              View 2522 Whispering Hills Chester, NY MLS# 1027103
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                1 of 35
                $355,000
                3

                Beds

                2.1

                Baths

                1,331

                Sq.Ft.

                2522 Whispering Hills

                Chester, NY

                Courtesy of HOWARD HANNA RAND REALTY
                View 151 Main Street Chester, NY MLS# 1031155
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                  1 of 16
                  $299,000
                  4

                  Beds

                  1.0

                  Baths

                  1,504

                  Sq.Ft.

                  151 Main Street

                  Chester, NY

                  Courtesy of HUDSON VALLEY GRIFFITH
                  View 2007 Whispering Hills Chester, NY MLS# 1030827
                    Save 2007 Whispering Hills Chester, NY MLS# 1030827
                    1 of 44
                    $279,999
                    2

                    Beds

                    1.1

                    Baths

                    1,086

                    Sq.Ft.

                    2007 Whispering Hills

                    Chester, NY

                    Courtesy of KELLER WILLIAMS REALTY
                    View 68 Conklingtown Road 1&2 Chester, NY MLS# 992189
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                      1 of 38
                      $575,000
                      6

                      Beds

                      2.0

                      Baths

                      43,560

                      Sq.Ft.

                      68 Conklingtown Road 1&2

                      Chester, NY

                      Courtesy of MS REALTY GROUP USA, INC
                      View 4008 Whispering Hills Drive Chester, NY MLS# 1027838
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                        1 of 33
                        $290,000
                        2

                        Beds

                        1.1

                        Baths

                        1,072

                        Sq.Ft.

                        4008 Whispering Hills Drive

                        Chester, NY

                        Courtesy of HOWARD HANNA RAND REALTY
                        View 7 Lakeview Drive Chester, NY MLS# 1028872
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                          1 of 29
                          $549,999
                          4

                          Beds

                          2.1

                          Baths

                          2,098

                          Sq.Ft.

                          7 Lakeview Drive

                          Chester, NY

                          Courtesy of HOWARD HANNA RAND REALTY
                          View 4114 Whispering Hills Chester, NY MLS# 1027245
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                            1 of 29
                            $389,900
                            3

                            Beds

                            2.0

                            Baths

                            1,393

                            Sq.Ft.

                            4114 Whispering Hills

                            Chester, NY

                            Courtesy of COLDWELL BANKER REALTY
                            View 424 Laroe Road Chester, NY MLS# 1013375
                              Save 424 Laroe Road Chester, NY MLS# 1013375
                              1 of 40
                              $634,999
                              4

                              Beds

                              3.0

                              Baths

                              2,316

                              Sq.Ft.

                              424 Laroe Road

                              Chester, NY

                              Courtesy of EPIQUE REALTY
                              View 3414 Whispering Hills Chester, NY MLS# 974398
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                              1 of 34
                              $349,999
                              3

                              Beds

                              2.0

                              Baths

                              1,316

                              Sq.Ft.

                              3414 Whispering Hills

                              Chester, NY

                              Courtesy of KW HUDSON VALLEY UNITED
                              View 11 Chandler Drive Chester, NY MLS# 1018371
                                Save 11 Chandler Drive Chester, NY MLS# 1018371
                                1 of 32
                                $499,999
                                3

                                Beds

                                2.1

                                Baths

                                1,908

                                Sq.Ft.

                                11 Chandler Drive

                                Chester, NY

                                Courtesy of COLDWELL BANKER REALTY
                                View 4118 Whispering Hills Drive Chester, NY MLS# 1018748
                                  Save 4118 Whispering Hills Drive Chester, NY MLS# 1018748
                                  1 of 22
                                  $329,000
                                  2

                                  Beds

                                  1.1

                                  Baths

                                  1,294

                                  Sq.Ft.

                                  4118 Whispering Hills Drive

                                  Chester, NY

                                  Courtesy of HOWARD HANNA RAND REALTY

                                  About Chester

                                  Listings in Chester, NY

                                  105

                                  Estimated median home price

                                  $669,000
                                  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 - 100K1
                                  $100K - 200K0
                                  $200K - 300K12
                                  $300K - 400K17
                                  $400K - 500K12
                                  $500K - 600K7
                                  $600K - 700K12
                                  $700K - 800K17
                                  $800K - 900K10
                                  $900K - 1M6
                                  $1M - Max11

                                  Homes for Sale by Type in Chester, NY

                                  Property TypeCount
                                  Single Family71
                                  Townhouse0
                                  Condo20
                                  Commercial7
                                  Rental25
                                  Lots and Land4
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family3
                                  Mobile Home0
                                  Farms0

                                  (Data as of 10/12/2026)

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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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