View 148 Brookside Avenue Chester, NY MLS# H6146719
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    1 of 3
    $799,000

    148 Brookside Avenue

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 16 Oxford Springs Road Chester, NY MLS# 935115
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    $750,000
    3

    Beds

    3.0

    Baths

    2,870

    Sq.Ft.

    16 Oxford Springs Road

    Chester, NY

    Courtesy of RE/MAX BENCHMARK REALTY GROUP
    View 5 Bens Way Chester, NY MLS# 959390
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      1 of 26
      $744,999
      4

      Beds

      2.1

      Baths

      2,544

      Sq.Ft.

      5 Bens Way

      Chester, NY

      Courtesy of KELLER WILLIAMS HUDSON VALLEY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 7 Park Place Chester, NY MLS# 927218
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        $730,000
        4

        Beds

        3.1

        Baths

        2,780

        Sq.Ft.

        7 Park Place

        Chester, NY

        Courtesy of CENTURY 21 FULL SERVICE REALTY
        View 9 Country Woods Drive Chester, NY MLS# 925049
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        $725,000
        5

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        2.1

        Baths

        3,124

        Sq.Ft.

        9 Country Woods Drive

        Chester, NY

        Courtesy of HOWARD HANNA RAND REALTY
        View 487 Black Meadow Road Chester, NY MLS# 960665
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          1 of 35
          $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
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            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 360 Prospect Road Chester, NY MLS# 944607
              Save 360 Prospect Road Chester, NY MLS# 944607
              1 of 50
              $699,000
              3

              Beds

              3.0

              Baths

              3,000

              Sq.Ft.

              360 Prospect Road

              Chester, NY

              Courtesy of EREALTY ADVISORS, INC
              View 34 Booth Road Chester, NY MLS# 961100
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              $699,000
              4

              Beds

              2.1

              Baths

              2,506

              Sq.Ft.

              34 Booth Road

              Chester, NY

              Courtesy of CENTURY 21 FULL SERVICE REALTY
              View 50 Elkay Drive Chester, NY MLS# 954329
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                $675,000
                Studio

                Beds

                0.0

                Baths

                87,120

                Sq.Ft.

                50 Elkay Drive

                Chester, NY

                Courtesy of POINT REALTY USA
                View 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
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                  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 391 Bull Mill Road Chester, NY MLS# 880804
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                  $509,999
                  2

                  Beds

                  2.0

                  Baths

                  1,714

                  Sq.Ft.

                  391 Bull Mill Road

                  Chester, NY

                  Courtesy of CENTURY 21 REALTY CENTER
                  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 70 Main Street Chester, NY MLS# 914556
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                      1 of 23
                      $475,000
                      4

                      Beds

                      2.1

                      Baths

                      1,357

                      Sq.Ft.

                      70 Main Street

                      Chester, NY

                      Courtesy of KELLER WILLIAMS HUDSON VALLEY
                      View 1367 Kings Highway Chester, NY MLS# 951876
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                        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 31 Hudson Street Chester, NY MLS# 963657
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                        1 of 25
                        $449,900
                        2

                        Beds

                        2.0

                        Baths

                        1,998

                        Sq.Ft.

                        31 Hudson Street

                        Chester, NY

                        Courtesy of BHG REAL ESTATE GREEN TEAM
                        View 108 Pine Hill Road Chester, NY MLS# 944582
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                        $444,000
                        4

                        Beds

                        1.1

                        Baths

                        1,780

                        Sq.Ft.

                        108 Pine Hill Road

                        Chester, NY

                        Courtesy of AVION
                        View 16 Oakland Avenue Chester, NY MLS# 939522
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                          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 7 Hambletonian Avenue Chester, NY MLS# 964090
                            Save 7 Hambletonian Avenue Chester, NY MLS# 964090
                            1 of 23
                            $425,000
                            2

                            Beds

                            1.0

                            Baths

                            1,026

                            Sq.Ft.

                            7 Hambletonian Avenue

                            Chester, NY

                            Courtesy of HOMESMART HOMES & ESTATES
                            View 2203 Whispering Hills Chester, NY MLS# 954443
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                            1 of 14
                            $370,000
                            3

                            Beds

                            2.1

                            Baths

                            1,331

                            Sq.Ft.

                            2203 Whispering Hills

                            Chester, NY

                            Courtesy of HOWARD HANNA RAND REALTY

                            About Chester

                            Listings in Chester, NY

                            57

                            Estimated median home price

                            $509,999
                            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 - 300K9
                            $300K - 400K9
                            $400K - 500K7
                            $500K - 600K1
                            $600K - 700K5
                            $700K - 800K6
                            $800K - 900K6
                            $900K - 1M4
                            $1M - Max7

                            Homes for Sale by Type in Chester, NY

                            Property TypeCount
                            Single Family30
                            Townhouse0
                            Condo11
                            Commercial5
                            Rental26
                            Lots and Land11
                            Condo/Town/CoOp0
                            CoOp0
                            Multi Family0
                            Mobile Home0
                            Farms0

                            (Data as of 3/16/2026)

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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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