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
    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 558 Pine Hill Road Chester, NY MLS# 958731
        Save 558 Pine Hill Road Chester, NY MLS# 958731
        1 of 50
        $599,000
        4

        Beds

        2.1

        Baths

        3,120

        Sq.Ft.

        558 Pine Hill Road

        Chester, NY

        Courtesy of EREALTY ADVISORS, INC
        The time to sell is now! THE TIME TO SELL IS NOW!
        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 7 Hambletonian Avenue Chester, NY MLS# 964090
            Save 7 Hambletonian Avenue Chester, NY MLS# 964090
            1 of 26
            $399,900
            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 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 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
                        $625,000
                        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
                            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 11
                              $369,900
                              3

                              Beds

                              2.1

                              Baths

                              1,331

                              Sq.Ft.

                              3910 Whispering Hills

                              Chester, NY

                              Courtesy of EXP REALTY
                              View 25 Oakland Avenue Chester, NY MLS# 949886
                                Save 25 Oakland Avenue Chester, NY MLS# 949886
                                1 of 17
                                $28,000,000
                                270,000

                                Sq.Ft.

                                25 Oakland Avenue

                                Chester, NY

                                Courtesy of EREALTY ADVISORS, INC
                                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 2948 State Route 94 Chester, NY MLS# 940751
                                      Save 2948 State Route 94 Chester, NY MLS# 940751
                                      1 of 45
                                      $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

                                        About Chester

                                        Listings in Chester, NY

                                        95

                                        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 - 100K0
                                        $100K - 200K3
                                        $200K - 300K5
                                        $300K - 400K14
                                        $400K - 500K14
                                        $500K - 600K7
                                        $600K - 700K6
                                        $700K - 800K11
                                        $800K - 900K12
                                        $900K - 1M7
                                        $1M - Max16

                                        Homes for Sale by Type in Chester, NY

                                        Property TypeCount
                                        Single Family65
                                        Townhouse0
                                        Condo10
                                        Commercial6
                                        Rental28
                                        Lots and Land13
                                        Condo/Town/CoOp0
                                        CoOp0
                                        Multi Family1
                                        Mobile Home0
                                        Farms0

                                        (Data as of 6/14/2026)

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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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