View 50 Hambletonian Avenue Chester, NY MLS# 1042882
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1 of 45
$550,000
3

Beds

2.0

Baths

1,583

Sq.Ft.

50 Hambletonian Avenue

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 7 Lakeview Drive Chester, NY MLS# 1028872
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    1 of 29
    $549,999
    4

    Beds

    2.1

    Baths

    2,098

    Sq.Ft.

    7 Lakeview Drive

    Chester, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 3318 State Route 94 Chester, NY MLS# 1008703
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      1 of 29
      $549,900
      3

      Beds

      2.0

      Baths

      2,138

      Sq.Ft.

      3318 State Route 94

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 11 Chandler Drive Chester, NY MLS# 1018371
        Save 11 Chandler Drive Chester, NY MLS# 1018371
        1 of 32
        $545,000
        3

        Beds

        2.1

        Baths

        1,908

        Sq.Ft.

        11 Chandler Drive

        Chester, NY

        Courtesy of COLDWELL BANKER REALTY
        View 24 Walnut Street Chester, NY MLS# 1004369
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          1 of 28
          $539,000
          4

          Beds

          2.1

          Baths

          2,698

          Sq.Ft.

          24 Walnut Street

          Chester, NY

          Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
          View 85 Surrey Road Chester, NY MLS# 984933
            Save 85 Surrey Road Chester, NY MLS# 984933
            1 of 35
            $524,900
            4

            Beds

            2.0

            Baths

            2,076

            Sq.Ft.

            85 Surrey Road

            Chester, NY

            Courtesy of KELLER WILLIAMS REALTY
            View 94 Booth Road Chester, NY MLS# 898870
              Save 94 Booth Road Chester, NY MLS# 898870
              1 of 23
              $520,000
              3

              Beds

              2.1

              Baths

              2,083

              Sq.Ft.

              94 Booth Road

              Chester, NY

              Courtesy of COMPASS GREATER NY, LLC
              View Main Street Chester, NY MLS# H6204360
                Save Main Street Chester, NY MLS# H6204360
                1 of 2
                $500,000
                Studio

                Beds

                0.0

                Baths

                36,098

                Sq.Ft.

                Main Street

                Chester, NY

                Courtesy of KELLER WILLIAMS REALTY
                View 5 N Hudson Street Chester, NY MLS# 976521
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                  1 of 28
                  $500,000
                  3

                  Beds

                  2.0

                  Baths

                  2,688

                  Sq.Ft.

                  5 N Hudson Street

                  Chester, NY

                  Courtesy of KELLER WILLIAMS REALTY
                  View 35 Maple Avenue Chester, NY MLS# 990509
                    Save 35 Maple Avenue Chester, NY MLS# 990509
                    1 of 29
                    $489,900
                    3

                    Beds

                    3.0

                    Baths

                    2,032

                    Sq.Ft.

                    35 Maple Avenue

                    Chester, NY

                    Courtesy of RE/MAX BENCHMARK REALTY GROUP
                    View 76 Surrey Road Chester, NY MLS# 1022518
                      Save 76 Surrey Road Chester, NY MLS# 1022518
                      1 of 44
                      $489,900
                      3

                      Beds

                      2.0

                      Baths

                      1,912

                      Sq.Ft.

                      76 Surrey Road

                      Chester, NY

                      Courtesy of EXP REALTY
                      View 32 Surrey Road Chester, NY MLS# 1040785
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                      1 of 39
                      $489,000
                      4

                      Beds

                      1.1

                      Baths

                      1,820

                      Sq.Ft.

                      32 Surrey Road

                      Chester, NY

                      Courtesy of EXP REALTY
                      View 21 Trotting Drive Chester, NY MLS# 1030740
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                      1 of 50
                      $475,000
                      3

                      Beds

                      2.0

                      Baths

                      1,624

                      Sq.Ft.

                      21 Trotting Drive

                      Chester, NY

                      Courtesy of KELLER WILLIAMS REALTY
                      View 70 Main Street Chester, NY MLS# 1034449
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                        1 of 27
                        $469,000
                        3

                        Beds

                        1.2

                        Baths

                        1,357

                        Sq.Ft.

                        70 Main Street

                        Chester, NY

                        Courtesy of CURASI REALTY, INC.
                        View 63 Hubshop Road Chester, NY MLS# 1039933
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                        Save 63 Hubshop Road Chester, NY MLS# 1039933
                        1 of 19
                        $459,000
                        4

                        Beds

                        2.1

                        Baths

                        2,060

                        Sq.Ft.

                        63 Hubshop Road

                        Chester, NY

                        Courtesy of KELLER WILLIAMS REALTY
                        View 66 Whitetail Run Chester, NY MLS# 1033721
                          Save 66 Whitetail Run Chester, NY MLS# 1033721
                          1 of 50
                          $449,000
                          3

                          Beds

                          1.1

                          Baths

                          1,500

                          Sq.Ft.

                          66 Whitetail Run

                          Chester, NY

                          Courtesy of HOWARD HANNA RAND REALTY
                          View 1367 Kings Highway Chester, NY MLS# 1036770
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                          1 of 16
                          $440,000
                          3

                          Beds

                          1.1

                          Baths

                          1,728

                          Sq.Ft.

                          1367 Kings Highway

                          Chester, NY

                          Courtesy of GREENE REALTY GROUP
                          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 492 Black Meadow Road Chester, NY MLS# 1002697
                              Save 492 Black Meadow Road Chester, NY MLS# 1002697
                              1 of 18
                              $399,000
                              Studio

                              Beds

                              0.0

                              Baths

                              2,003,760

                              Sq.Ft.

                              492 Black Meadow Road

                              Chester, NY

                              Courtesy of EXP REALTY
                              View 4114 Whispering Hills Chester, NY MLS# 1027245
                                Save 4114 Whispering Hills Chester, NY MLS# 1027245
                                1 of 29
                                $389,900
                                3

                                Beds

                                2.0

                                Baths

                                1,393

                                Sq.Ft.

                                4114 Whispering Hills

                                Chester, NY

                                Courtesy of COLDWELL BANKER REALTY

                                About Chester

                                Listings in Chester, NY

                                109

                                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 - 100K1
                                $100K - 200K0
                                $200K - 300K8
                                $300K - 400K18
                                $400K - 500K12
                                $500K - 600K9
                                $600K - 700K12
                                $700K - 800K20
                                $800K - 900K10
                                $900K - 1M6
                                $1M - Max13

                                Homes for Sale by Type in Chester, NY

                                Property TypeCount
                                Single Family79
                                Townhouse0
                                Condo17
                                Commercial6
                                Rental23
                                Lots and Land5
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family2
                                Mobile Home0
                                Farms0

                                (Data as of 8/30/2026)

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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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