View 147 Main Street Chester, NY MLS# 1052484
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$549,000
4

Beds

2.0

Baths

2,824

Sq.Ft.

147 Main Street

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 24 Walnut Street Chester, NY MLS# 1004369
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    1 of 28
    $525,000
    4

    Beds

    2.1

    Baths

    2,698

    Sq.Ft.

    24 Walnut Street

    Chester, NY

    Courtesy of KELLER WILLIAMS VILLAGE SQ RLT
    View 19 Meadow Avenue Chester, NY MLS# 1050131
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      1 of 18
      $525,000
      2

      Beds

      2.0

      Baths

      1,910

      Sq.Ft.

      19 Meadow Avenue

      Chester, NY

      Courtesy of RE/MAX TOWN & COUNTRY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 94 Booth Road Chester, NY MLS# 1050173
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      $525,000
      3

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      2.1

      Baths

      2,441

      Sq.Ft.

      94 Booth Road

      Chester, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View Main Street Chester, NY MLS# H6204360
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        $500,000
        0.0

        Baths

        36,098

        Sq.Ft.

        Main Street

        Chester, NY

        Courtesy of KELLER WILLIAMS REALTY
        View 11 Chandler Drive Chester, NY MLS# 1018371
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          1 of 32
          $499,999
          3

          Beds

          2.1

          Baths

          1,908

          Sq.Ft.

          11 Chandler Drive

          Chester, NY

          Courtesy of COLDWELL BANKER REALTY
          View 21 Trotting Drive Chester, NY MLS# 1030740
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          1 of 49
          $475,000
          3

          Beds

          2.0

          Baths

          1,624

          Sq.Ft.

          21 Trotting Drive

          Chester, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 32 Surrey Road Chester, NY MLS# 1040785
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            1 of 39
            $475,000
            4

            Beds

            1.1

            Baths

            1,820

            Sq.Ft.

            32 Surrey Road

            Chester, NY

            Courtesy of EXP REALTY
            View 63 Hubshop Road Chester, NY MLS# 1039933
              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 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 66 Whitetail Run Chester, NY MLS# 1033721
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                  1 of 50
                  $435,000
                  3

                  Beds

                  1.1

                  Baths

                  1,500

                  Sq.Ft.

                  66 Whitetail Run

                  Chester, NY

                  Courtesy of HOWARD HANNA RAND REALTY
                  View 70 Main Street Chester, NY MLS# 1034449
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                    1 of 27
                    $425,000
                    3

                    Beds

                    1.2

                    Baths

                    1,357

                    Sq.Ft.

                    70 Main Street

                    Chester, NY

                    Courtesy of CURASI REALTY, INC.
                    View 492 Black Meadow Road Chester, NY MLS# 1002697
                      Save 492 Black Meadow Road Chester, NY MLS# 1002697
                      1 of 18
                      $399,000
                      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 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 260 Gibson Hill Road Chester, NY MLS# 1044316
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                            1 of 22
                            $374,900
                            3

                            Beds

                            1.1

                            Baths

                            1,644

                            Sq.Ft.

                            260 Gibson Hill Road

                            Chester, NY

                            Courtesy of KELLER WILLIAMS REALTY
                            View 4704 Whispering Hills Chester, NY MLS# 1038636
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                              1 of 19
                              $370,000
                              3

                              Beds

                              2.1

                              Baths

                              1,331

                              Sq.Ft.

                              4704 Whispering Hills

                              Chester, NY

                              Courtesy of SAHAGIAN REALTY LLC
                              View 3211 Whispering Hills Chester, NY MLS# 1046996
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                              1 of 40
                              $370,000
                              3

                              Beds

                              2.0

                              Baths

                              1,316

                              Sq.Ft.

                              3211 Whispering Hills

                              Chester, NY

                              Courtesy of RE/MAX BENCHMARK REALTY GROUP
                              View 2921 Whispering Hills Chester, NY MLS# 1043986
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                                1 of 42
                                $364,900
                                3

                                Beds

                                2.1

                                Baths

                                1,331

                                Sq.Ft.

                                2921 Whispering Hills

                                Chester, NY

                                Courtesy of ARC REALTY 1 IN SALES
                                View 3409 Whispering Hills Chester, NY MLS# 1032618
                                  Save 3409 Whispering Hills Chester, NY MLS# 1032618
                                  1 of 24
                                  $360,000
                                  3

                                  Beds

                                  2.1

                                  Baths

                                  1,331

                                  Sq.Ft.

                                  3409 Whispering Hills

                                  Chester, NY

                                  Courtesy of HOWARD HANNA RAND REALTY

                                  About Chester

                                  Listings in Chester, NY

                                  101

                                  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 - 100K1
                                  $100K - 200K0
                                  $200K - 300K10
                                  $300K - 400K18
                                  $400K - 500K8
                                  $500K - 600K9
                                  $600K - 700K11
                                  $700K - 800K17
                                  $800K - 900K10
                                  $900K - 1M6
                                  $1M - Max11

                                  Homes for Sale by Type in Chester, NY

                                  Property TypeCount
                                  Single Family67
                                  Townhouse0
                                  Condo21
                                  Commercial6
                                  Rental22
                                  Lots and Land4
                                  Condo/Town/CoOp0
                                  CoOp0
                                  Multi Family3
                                  Mobile Home0
                                  Farms0

                                  (Data as of 10/6/2026)

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                                  Information deemed reliable but not guaranteed.

                                  The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the NJMLS. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.

                                  All information deemed reliable but not guaranteed. Last date updated: 10/6/2026.

                                  Source: New Jersey Multiple Listing Service, Inc.

                                  © 2026 New Jersey Multiple Listing Service, Inc. All rights reserved.

                                  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.