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
        The time to sell is now! THE TIME TO SELL IS NOW!
        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 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 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
                            • Virtual Tour
                            Save 3910 Whispering Hills Chester, NY MLS# 946789
                            1 of 9
                            $369,900
                            3

                            Beds

                            2.1

                            Baths

                            1,331

                            Sq.Ft.

                            3910 Whispering Hills

                            Chester, NY

                            Courtesy of EXP REALTY
                            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 Oxford Road Chester, NY MLS# 945194
                                Save Oxford Road Chester, NY MLS# 945194
                                1 of 1
                                $199,000
                                Studio

                                Beds

                                0.0

                                Baths

                                113,256

                                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 101 Oxford Road Chester, NY MLS# 943068
                                  • Adult Community
                                  Save 101 Oxford Road Chester, NY MLS# 943068
                                  1 of 1
                                  $639,000
                                  3

                                  Beds

                                  1.1

                                  Baths

                                  1,816

                                  Sq.Ft.

                                  101 Oxford Road

                                  Chester, NY

                                  Courtesy of LOOP REALTY INC
                                  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

                                    About Chester

                                    Listings in Chester, NY

                                    69

                                    Estimated median home price

                                    $699,000
                                    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 - 300K8
                                    $300K - 400K11
                                    $400K - 500K7
                                    $500K - 600K2
                                    $600K - 700K7
                                    $700K - 800K11
                                    $800K - 900K6
                                    $900K - 1M4
                                    $1M - Max10

                                    Homes for Sale by Type in Chester, NY

                                    Property TypeCount
                                    Single Family42
                                    Townhouse0
                                    Condo10
                                    Commercial5
                                    Rental26
                                    Lots and Land12
                                    Condo/Town/CoOp0
                                    CoOp0
                                    Multi Family0
                                    Mobile Home0
                                    Farms0

                                    (Data as of 4/20/2026)

                                    Browse Neighborhoods

                                    Find Properties in Chester, NY

                                    Chester, NY Information

                                    Find Properties by Zip

                                    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.

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