View 5 Roggia Road Chester, NY MLS# 978824
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$450,000
3

Beds

2.0

Baths

1,882

Sq.Ft.

5 Roggia Road

Chester, NY

Courtesy of NAZMA REAL ESTATE LLC
View 66 Whitetail Run Chester, NY MLS# 1033721
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$449,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

66 Whitetail Run

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 151 Laroe Road Chester, NY MLS# 995916
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    1 of 43
    $430,000
    3

    Beds

    1.1

    Baths

    1,177

    Sq.Ft.

    151 Laroe Road

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    The time to sell is now! THE TIME TO SELL IS NOW!
    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 11 Oxford Depot Chester, NY MLS# 1002651
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        1 of 26
        $425,000
        3

        Beds

        2.0

        Baths

        1,748

        Sq.Ft.

        11 Oxford Depot

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        View 492 Black Meadow Road Chester, NY MLS# 1002697
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          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
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          1 of 29
          $389,900
          3

          Beds

          2.0

          Baths

          1,393

          Sq.Ft.

          4114 Whispering Hills

          Chester, NY

          Courtesy of COLDWELL BANKER REALTY
          View 185 Oxford Road Chester, NY MLS# 1019170
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            1 of 49
            $389,000
            3

            Beds

            1.0

            Baths

            1,062

            Sq.Ft.

            185 Oxford Road

            Chester, NY

            Courtesy of KELLER WILLIAMS HUDSON VALLEY
            View 7 Hambletonian Avenue Chester, NY MLS# 964090
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              1 of 26
              $379,900
              2

              Beds

              1.0

              Baths

              1,026

              Sq.Ft.

              7 Hambletonian Avenue

              Chester, NY

              Courtesy of HOMESMART HOMES & ESTATES
              View 3815 Whispering Hills Drive Chester, NY MLS# 1000359
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                1 of 50
                $370,000
                3

                Beds

                2.1

                Baths

                1,331

                Sq.Ft.

                3815 Whispering Hills Drive

                Chester, NY

                Courtesy of MK REALTY INC
                View 2522 Whispering Hills Chester, NY MLS# 1027103
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                1 of 35
                $369,000
                3

                Beds

                2.1

                Baths

                1,331

                Sq.Ft.

                2522 Whispering Hills

                Chester, NY

                Courtesy of HOWARD HANNA RAND REALTY
                View 2703 Whispering Hills Chester, NY MLS# 1016415
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                  1 of 39
                  $365,000
                  3

                  Beds

                  2.1

                  Baths

                  1,331

                  Sq.Ft.

                  2703 Whispering Hills

                  Chester, NY

                  Courtesy of KELLER WILLIAMS REALTY
                  View 2 Virginia Lane Chester, NY MLS# H6215339
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                    1 of 4
                    $350,000
                    Studio

                    Beds

                    0.0

                    Baths

                    235,224

                    Sq.Ft.

                    2 Virginia Lane

                    Chester, NY

                    Courtesy of KELLER WILLIAMS REALTY
                    View Odyssey Drive Chester, NY MLS# 858370
                      Save Odyssey Drive Chester, NY MLS# 858370
                      1 of 4
                      $350,000
                      Studio

                      Beds

                      0.0

                      Baths

                      222,156

                      Sq.Ft.

                      Odyssey Drive

                      Chester, NY

                      Courtesy of KELLER WILLIAMS REALTY
                      View 220 Oxford Road Chester, NY MLS# 907969
                        Save 220 Oxford Road Chester, NY MLS# 907969
                        1 of 1
                        $350,000
                        Studio

                        Beds

                        0.0

                        Baths

                        274,428

                        Sq.Ft.

                        220 Oxford Road

                        Chester, NY

                        Courtesy of EXIT REALTY VENTURE
                        View 2604 Whispering Hills Chester, NY MLS# 1025165
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                          1 of 35
                          $350,000
                          3

                          Beds

                          2.1

                          Baths

                          1,086

                          Sq.Ft.

                          2604 Whispering Hills

                          Chester, NY

                          Courtesy of HOMESMART HOMES & ESTATES
                          View 151 Main Street Chester, NY MLS# 1031155
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                          1 of 16
                          $350,000
                          4

                          Beds

                          1.0

                          Baths

                          1,504

                          Sq.Ft.

                          151 Main Street

                          Chester, NY

                          Courtesy of HUDSON VALLEY GRIFFITH
                          View 3414 Whispering Hills Chester, NY MLS# 974398
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                          1 of 34
                          $349,999
                          3

                          Beds

                          2.0

                          Baths

                          1,316

                          Sq.Ft.

                          3414 Whispering Hills

                          Chester, NY

                          Courtesy of KW HUDSON VALLEY UNITED
                          View 1311 Whispering Hills Chester, NY MLS# 983111
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                            1 of 32
                            $329,900
                            3

                            Beds

                            2.0

                            Baths

                            1,316

                            Sq.Ft.

                            1311 Whispering Hills

                            Chester, NY

                            Courtesy of KELLER WILLIAMS REALTY
                            View 4118 Whispering Hills Drive Chester, NY MLS# 1018748
                              Save 4118 Whispering Hills Drive Chester, NY MLS# 1018748
                              1 of 22
                              $329,000
                              2

                              Beds

                              1.1

                              Baths

                              1,294

                              Sq.Ft.

                              4118 Whispering Hills Drive

                              Chester, NY

                              Courtesy of HOWARD HANNA RAND REALTY

                              About Chester

                              Listings in Chester, NY

                              99

                              Estimated median home price

                              $699,995
                              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 - 200K1
                              $200K - 300K5
                              $300K - 400K17
                              $400K - 500K11
                              $500K - 600K9
                              $600K - 700K8
                              $700K - 800K17
                              $800K - 900K12
                              $900K - 1M7
                              $1M - Max12

                              Homes for Sale by Type in Chester, NY

                              Property TypeCount
                              Single Family70
                              Townhouse0
                              Condo14
                              Commercial6
                              Rental22
                              Lots and Land7
                              Condo/Town/CoOp0
                              CoOp0
                              Multi Family2
                              Mobile Home0
                              Farms0

                              (Data as of 8/4/2026)

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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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