View 70 Main Street Chester, NY MLS# 1034449
    Save 70 Main Street Chester, NY MLS# 1034449
    1 of 27
    $469,000
    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
      OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM
      $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
        The time to sell is now! THE TIME TO SELL IS NOW!
        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
          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
                          Save 2604 Whispering Hills Chester, NY MLS# 1025165
                          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
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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

                                      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 - 600K10
                                      $600K - 700K11
                                      $700K - 800K16
                                      $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 10/1/2026)

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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: 10/1/2026.

                                      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.

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