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
        The time to sell is now! THE TIME TO SELL IS NOW!
        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 487 Black Meadow Road Chester, NY MLS# 960665
                  Save 487 Black Meadow Road Chester, NY MLS# 960665
                  1 of 50
                  OPEN HOUSE: Sunday 4/26 12:00 PM - 3:30 PM
                  $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

                                    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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