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
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      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
        The time to sell is now! THE TIME TO SELL IS NOW!
        View 5 Gabriels Drive Chester, NY MLS# 952148
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        1 of 49
        $899,000
        4

        Beds

        2.1

        Baths

        2,722

        Sq.Ft.

        5 Gabriels Drive

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        View 12 Damian Court Chester, NY MLS# 950640
          Save 12 Damian Court Chester, NY MLS# 950640
          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 108 Pine Hill Road Chester, NY MLS# 944582
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              1 of 37
              $429,000
              4

              Beds

              1.1

              Baths

              1,780

              Sq.Ft.

              108 Pine Hill Road

              Chester, NY

              Courtesy of AVION
              View 3308 Whispering Hills Drive Chester, NY MLS# 924165
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                1 of 30
                $289,000
                2

                Beds

                1.1

                Baths

                1,072

                Sq.Ft.

                3308 Whispering Hills Drive

                Chester, NY

                Courtesy of HOWARD HANNA RAND 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
                  View 360 Prospect Road Chester, NY MLS# 944607
                    Save 360 Prospect Road Chester, NY MLS# 944607
                    1 of 50
                    $699,000
                    3

                    Beds

                    3.0

                    Baths

                    3,000

                    Sq.Ft.

                    360 Prospect Road

                    Chester, NY

                    Courtesy of EREALTY ADVISORS, INC
                    View 3120 Whispering Hills Chester, NY MLS# 941582
                      Save 3120 Whispering Hills Chester, NY MLS# 941582
                      1 of 18
                      $299,000
                      2

                      Beds

                      1.1

                      Baths

                      1,072

                      Sq.Ft.

                      3120 Whispering Hills

                      Chester, NY

                      Courtesy of JOHN J LEASE REALTORS INC
                      View 3917 Whispering Hills Chester, NY MLS# 942965
                        Save 3917 Whispering Hills Chester, NY MLS# 942965
                        1 of 28
                        $305,000
                        2

                        Beds

                        1.1

                        Baths

                        1,072

                        Sq.Ft.

                        3917 Whispering Hills

                        Chester, NY

                        Courtesy of KELLER WILLIAMS HUDSON VALLEY
                        View 2948 State Route 94 Chester, NY MLS# 940751
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                          1 of 45
                          OPEN HOUSE: Sunday 3/22 11:00 AM - 1:00 PM
                          $1,300,000
                          4

                          Beds

                          2.1

                          Baths

                          3,866

                          Sq.Ft.

                          2948 State Route 94

                          Chester, NY

                          Courtesy of TUXEDO HUDSON REALTY CORP
                          View 16 Oakland Avenue Chester, NY MLS# 939522
                            Save 16 Oakland Avenue Chester, NY MLS# 939522
                            1 of 49
                            $425,000
                            4

                            Beds

                            2.1

                            Baths

                            2,090

                            Sq.Ft.

                            16 Oakland Avenue

                            Chester, NY

                            Courtesy of BHG REAL ESTATE GREEN TEAM
                            View 16 Oxford Springs Road Chester, NY MLS# 935115
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                            1 of 43
                            $750,000
                            3

                            Beds

                            3.0

                            Baths

                            2,870

                            Sq.Ft.

                            16 Oxford Springs Road

                            Chester, NY

                            Courtesy of RE/MAX BENCHMARK REALTY GROUP
                            View 1503 Whispering Hills Chester, NY MLS# 937839
                              Save 1503 Whispering Hills Chester, NY MLS# 937839
                              1 of 17
                              $309,900
                              3

                              Beds

                              2.1

                              Baths

                              1,331

                              Sq.Ft.

                              1503 Whispering Hills

                              Chester, NY

                              Courtesy of CENTURY 21 E & M WILLIAMS RLTY
                              View 1401 Whispering Hills Chester, NY MLS# 935471
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                                1 of 33
                                $289,500
                                2

                                Beds

                                1.0

                                Baths

                                1,084

                                Sq.Ft.

                                1401 Whispering Hills

                                Chester, NY

                                Courtesy of HOWARD HANNA RAND REALTY

                                About Chester

                                Listings in Chester, NY

                                58

                                Estimated median home price

                                $505,000
                                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 - 300K9
                                $300K - 400K9
                                $400K - 500K8
                                $500K - 600K1
                                $600K - 700K5
                                $700K - 800K6
                                $800K - 900K6
                                $900K - 1M4
                                $1M - Max7

                                Homes for Sale by Type in Chester, NY

                                Property TypeCount
                                Single Family31
                                Townhouse0
                                Condo11
                                Commercial5
                                Rental22
                                Lots and Land11
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family0
                                Mobile Home0
                                Farms0

                                (Data as of 3/18/2026)

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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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