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
        The time to sell is now! THE TIME TO SELL IS NOW!
        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 31 Hudson Street Chester, NY MLS# 963657
            Save 31 Hudson Street Chester, NY MLS# 963657
            1 of 25
            $449,900
            2

            Beds

            2.0

            Baths

            1,998

            Sq.Ft.

            31 Hudson Street

            Chester, NY

            Courtesy of BHG REAL ESTATE GREEN TEAM
            View 558 Pine Hill Road Chester, NY MLS# 958731
              Save 558 Pine Hill Road Chester, NY MLS# 958731
              1 of 50
              $799,000
              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 1005 Whispering Hills Chester, NY MLS# 964957
                  Save 1005 Whispering Hills Chester, NY MLS# 964957
                  1 of 1
                  $249,900
                  2

                  Beds

                  1.1

                  Baths

                  1,053

                  Sq.Ft.

                  1005 Whispering Hills

                  Chester, NY

                  Courtesy of ARC REALTY 1 IN SALES
                  View 7 Hambletonian Avenue Chester, NY MLS# 964090
                    Save 7 Hambletonian Avenue Chester, NY MLS# 964090
                    1 of 23
                    $410,000
                    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
                      • Virtual Tour
                      Save 34 Booth Road Chester, NY MLS# 961100
                      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 4 Debbie Court Chester, NY MLS# 962813
                        Save 4 Debbie Court Chester, NY MLS# 962813
                        1 of 50
                        $840,000
                        5

                        Beds

                        5.1

                        Baths

                        5,403

                        Sq.Ft.

                        4 Debbie Court

                        Chester, NY

                        Courtesy of FLAG REALTY GROUP
                        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 5 Bens Way Chester, NY MLS# 959390
                              Save 5 Bens Way Chester, NY MLS# 959390
                              1 of 26
                              $699,999
                              4

                              Beds

                              2.1

                              Baths

                              2,544

                              Sq.Ft.

                              5 Bens Way

                              Chester, NY

                              Courtesy of KELLER WILLIAMS HUDSON VALLEY
                              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
                                    $650,000
                                    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
                                      Save 1367 Kings Highway Chester, NY MLS# 951876
                                      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
                                      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

                                        About Chester

                                        Listings in Chester, NY

                                        68

                                        Estimated median home price

                                        $699,495
                                        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 - 300K6
                                        $300K - 400K11
                                        $400K - 500K7
                                        $500K - 600K2
                                        $600K - 700K7
                                        $700K - 800K11
                                        $800K - 900K7
                                        $900K - 1M4
                                        $1M - Max10

                                        Homes for Sale by Type in Chester, NY

                                        Property TypeCount
                                        Single Family43
                                        Townhouse0
                                        Condo8
                                        Commercial5
                                        Rental25
                                        Lots and Land12
                                        Condo/Town/CoOp0
                                        CoOp0
                                        Multi Family0
                                        Mobile Home0
                                        Farms0

                                        (Data as of 4/21/2026)

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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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