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
      Save 2522 Whispering Hills Chester, NY MLS# 1027103
      1 of 35
      $359,000
      3

      Beds

      2.1

      Baths

      1,331

      Sq.Ft.

      2522 Whispering Hills

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 3 Hilltop Lane Chester, NY MLS# 1031147
        Save 3 Hilltop Lane Chester, NY MLS# 1031147
        1 of 1
        $750,000
        5

        Beds

        2.1

        Baths

        2,700

        Sq.Ft.

        3 Hilltop Lane

        Chester, NY

        Courtesy of MK REALTY INC
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 151 Main Street Chester, NY MLS# 1031155
          Save 151 Main Street Chester, NY MLS# 1031155
          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
              Save 68 Conklingtown Road 1&2 Chester, NY MLS# 992189
              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
                Save 4008 Whispering Hills Drive Chester, NY MLS# 1027838
                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 1 Hilltop Lane Chester, NY MLS# 1031045
                  Save 1 Hilltop Lane Chester, NY MLS# 1031045
                  1 of 1
                  $750,000
                  5

                  Beds

                  2.1

                  Baths

                  2,700

                  Sq.Ft.

                  1 Hilltop Lane

                  Chester, NY

                  Courtesy of MK REALTY INC
                  View 7 Lakeview Drive Chester, NY MLS# 1028872
                    Save 7 Lakeview Drive Chester, NY MLS# 1028872
                    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 197 Oxford Road Chester, NY MLS# 1012284
                    • Virtual Tour
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                    1 of 36
                    $799,000
                    4

                    Beds

                    2.1

                    Baths

                    3,070

                    Sq.Ft.

                    197 Oxford Road

                    Chester, NY

                    Courtesy of HOWARD HANNA RAND REALTY
                    View 4114 Whispering Hills Chester, NY MLS# 1027245
                      Save 4114 Whispering Hills Chester, NY MLS# 1027245
                      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 2604 Whispering Hills Chester, NY MLS# 1025165
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                        1 of 35
                        $350,000
                        3

                        Beds

                        2.1

                        Baths

                        1,086

                        Sq.Ft.

                        2604 Whispering Hills

                        Chester, NY

                        Courtesy of HOMESMART HOMES & ESTATES
                        View 2 Hemlock Court Chester, NY MLS# 1025992
                          Save 2 Hemlock Court Chester, NY MLS# 1025992
                          1 of 3
                          $750,000
                          5

                          Beds

                          2.1

                          Baths

                          2,700

                          Sq.Ft.

                          2 Hemlock Court

                          Chester, NY

                          Courtesy of MK REALTY INC
                          View 1 Arborvitae Court Chester, NY MLS# 1024518
                            Save 1 Arborvitae Court Chester, NY MLS# 1024518
                            1 of 1
                            $725,000
                            3

                            Beds

                            2.1

                            Baths

                            2,677

                            Sq.Ft.

                            1 Arborvitae Court

                            Chester, NY

                            Courtesy of MK REALTY INC
                            View 3414 Whispering Hills Chester, NY MLS# 974398
                            • Virtual Tour
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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
                              OPEN HOUSE: Sunday 10/4 12:30 PM - 2:30 PM
                              $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
                                View 5 Hilltop Lane Chester, NY MLS# 1020076
                                  Save 5 Hilltop Lane Chester, NY MLS# 1020076
                                  1 of 5
                                  $850,000
                                  5

                                  Beds

                                  2.1

                                  Baths

                                  3,200

                                  Sq.Ft.

                                  5 Hilltop Lane

                                  Chester, NY

                                  Courtesy of MK REALTY INC
                                  View 3 Hemlock Court Chester, NY MLS# 1020128
                                    Save 3 Hemlock Court Chester, NY MLS# 1020128
                                    1 of 50
                                    $750,000
                                    5

                                    Beds

                                    2.1

                                    Baths

                                    2,700

                                    Sq.Ft.

                                    3 Hemlock Court

                                    Chester, NY

                                    Courtesy of MK REALTY INC
                                    View 2119 Whispering Hills Chester, NY MLS# 1019548
                                      Save 2119 Whispering Hills Chester, NY MLS# 1019548
                                      1 of 32
                                      $295,000
                                      2

                                      Beds

                                      1.1

                                      Baths

                                      1,086

                                      Sq.Ft.

                                      2119 Whispering Hills

                                      Chester, NY

                                      Courtesy of HOWARD HANNA RAND REALTY

                                      About Chester

                                      Listings in Chester, NY

                                      101

                                      Estimated median home price

                                      $675,000
                                      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 - 300K10
                                      $300K - 400K18
                                      $400K - 500K8
                                      $500K - 600K9
                                      $600K - 700K11
                                      $700K - 800K17
                                      $800K - 900K10
                                      $900K - 1M6
                                      $1M - Max11

                                      Homes for Sale by Type in Chester, NY

                                      Property TypeCount
                                      Single Family67
                                      Townhouse0
                                      Condo21
                                      Commercial6
                                      Rental22
                                      Lots and Land4
                                      Condo/Town/CoOp0
                                      CoOp0
                                      Multi Family3
                                      Mobile Home0
                                      Farms0

                                      (Data as of 10/3/2026)

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                                      Information deemed reliable but not guaranteed.

                                      The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the NJMLS. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.

                                      All information deemed reliable but not guaranteed. Last date updated: 10/4/2026.

                                      Source: New Jersey Multiple Listing Service, Inc.

                                      © 2026 New Jersey Multiple Listing Service, Inc. All rights reserved.

                                      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.

                                      Information Copyright 2021, OneKey® MLS. All Rights Reserved.