View 26 Bridle Lane Chester, NY MLS# 1011224
    Save 26 Bridle Lane Chester, NY MLS# 1011224
    1 of 29
    $685,000
    4

    Beds

    2.1

    Baths

    1,718

    Sq.Ft.

    26 Bridle Lane

    Chester, NY

    Courtesy of OWNER ENTRY.COM
    View 335 Laroe Road Chester, NY MLS# 1009848
      Save 335 Laroe Road Chester, NY MLS# 1009848
      1 of 35
      $675,000
      4

      Beds

      2.1

      Baths

      2,784

      Sq.Ft.

      335 Laroe Road

      Chester, NY

      Courtesy of COLDWELL BANKER CHOICE PROP.
      View 3318 State Route 94 Chester, NY MLS# 1008703
        Save 3318 State Route 94 Chester, NY MLS# 1008703
        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 24 Walnut Street Chester, NY MLS# 1004369
          Save 24 Walnut Street Chester, NY MLS# 1004369
          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 45 Whitetail Run Chester, NY MLS# 999741
          • Virtual Tour
          Save 45 Whitetail Run Chester, NY MLS# 999741
          1 of 47
          $825,000
          4

          Beds

          2.1

          Baths

          2,732

          Sq.Ft.

          45 Whitetail Run

          Chester, NY

          Courtesy of HUDSON VALLEY HOME CONNECTION
          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 60 Whitetail Run Chester, NY MLS# 1002536
              Save 60 Whitetail Run Chester, NY MLS# 1002536
              1 of 7
              $900,000
              4

              Beds

              2.1

              Baths

              2,588

              Sq.Ft.

              60 Whitetail Run

              Chester, NY

              Courtesy of REALTY BLUE CORP
              View 220 Oxford Road Chester, NY MLS# 000137
                Save 220 Oxford Road Chester, NY MLS# 000137
                1 of 20
                $894,000
                3

                Beds

                3.1

                Baths

                3,535

                Sq.Ft.

                220 Oxford Road

                Chester, NY

                Courtesy of BLOOMING REALTY
                View 4 Debbie Court Chester, NY MLS# 995223
                  Save 4 Debbie Court Chester, NY MLS# 995223
                  1 of 49
                  $785,000
                  5

                  Beds

                  5.1

                  Baths

                  5,403

                  Sq.Ft.

                  4 Debbie Court

                  Chester, NY

                  Courtesy of FLAG REALTY GROUP
                  View 58 Nancy Lane Chester, NY MLS# 995624
                    Save 58 Nancy Lane Chester, NY MLS# 995624
                    1 of 49
                    OPEN HOUSE: Sunday 10/4 12:00 PM - 2:00 PM
                    $744,999
                    4

                    Beds

                    2.1

                    Baths

                    2,718

                    Sq.Ft.

                    58 Nancy Lane

                    Chester, NY

                    Courtesy of HOWARD HANNA RAND REALTY
                    View 2820 Whispering Hills Chester, NY MLS# 986005
                      Save 2820 Whispering Hills Chester, NY MLS# 986005
                      1 of 32
                      $319,900
                      2

                      Beds

                      1.1

                      Baths

                      1,072

                      Sq.Ft.

                      2820 Whispering Hills

                      Chester, NY

                      Courtesy of R2M REALTY INC
                      View 2 Primrose Lane Chester, NY MLS# 991517
                        Save 2 Primrose Lane Chester, NY MLS# 991517
                        1 of 42
                        $849,900
                        4

                        Beds

                        3.0

                        Baths

                        2,370

                        Sq.Ft.

                        2 Primrose Lane

                        Chester, NY

                        Courtesy of Weichert Realtors - Monroe
                        View 149 Creamery Pond Road Chester, NY MLS# 986323
                        • Virtual Tour
                        Save 149 Creamery Pond Road Chester, NY MLS# 986323
                        1 of 46
                        $775,000
                        3

                        Beds

                        3.0

                        Baths

                        2,740

                        Sq.Ft.

                        149 Creamery Pond Road

                        Chester, NY

                        Courtesy of KELLER WILLIAMS REALTY
                        View 1311 Whispering Hills Chester, NY MLS# 983111
                          Save 1311 Whispering Hills Chester, NY MLS# 983111
                          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 90 Pewter Circle Chester, NY MLS# 981270
                            Save 90 Pewter Circle Chester, NY MLS# 981270
                            1 of 5
                            $759,900
                            4

                            Beds

                            2.1

                            Baths

                            2,250

                            Sq.Ft.

                            90 Pewter Circle

                            Chester, NY

                            Courtesy of KELLER WILLIAMS REALTY
                            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 552 Pine Hill Road Chester, NY MLS# 958740
                                  Save 552 Pine Hill Road Chester, NY MLS# 958740
                                  1 of 1
                                  $299,000
                                  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
                                    $379,900
                                    2

                                    Beds

                                    1.0

                                    Baths

                                    1,026

                                    Sq.Ft.

                                    7 Hambletonian Avenue

                                    Chester, NY

                                    Courtesy of HOMESMART HOMES & ESTATES
                                    View 487 Black Meadow Road Chester, NY MLS# 960665
                                      Save 487 Black Meadow Road Chester, NY MLS# 960665
                                      1 of 49
                                      $699,995
                                      6

                                      Beds

                                      3.1

                                      Baths

                                      4,204

                                      Sq.Ft.

                                      487 Black Meadow Road

                                      Chester, NY

                                      Courtesy of JOSEPH BARATTA COMPANY 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 10/3/2026)

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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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