View 9 Country Woods Drive Chester, NY MLS# 925049
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$725,000
5

Beds

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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    $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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      $699,990
      4

      Beds

      3.0

      Baths

      1,867

      Sq.Ft.

      34 Mountainside Drive

      Chester, NY

      Courtesy of OUR HOUSE REAL ESTATE GROUP
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 360 Prospect Road Chester, NY MLS# 944607
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        $699,000
        3

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        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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        OPEN HOUSE: Sunday 3/8 12:00 PM - 2:00 PM
        $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 101 Oxford Road Chester, NY MLS# 943068
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          $669,000
          3

          Beds

          1.1

          Baths

          1,816

          Sq.Ft.

          101 Oxford Road

          Chester, NY

          Courtesy of LOOP REALTY INC
          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 44 Cedar Pond Lane Chester, NY MLS# 942578
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              $600,000
              3

              Beds

              2.0

              Baths

              1,876

              Sq.Ft.

              44 Cedar Pond Lane

              Chester, NY

              Courtesy of EXP REALTY
              View 391 Bull Mill Road Chester, NY MLS# 880804
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              $509,999
              3

              Beds

              2.0

              Baths

              1,800

              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 6 Vista Drive Chester, NY MLS# 944968
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                $499,900
                3

                Beds

                2.1

                Baths

                1,934

                Sq.Ft.

                6 Vista Drive

                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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                    $449,000
                    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
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                      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 2915 Whispering Hills Chester, NY MLS# 927990
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                      1 of 23
                      $369,000
                      3

                      Beds

                      2.1

                      Baths

                      1,331

                      Sq.Ft.

                      2915 Whispering Hills

                      Chester, NY

                      Courtesy of CENTURY 21 FULL SERVICE 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

                        About Chester

                        Listings in Chester, NY

                        60

                        Estimated median home price

                        $555,000
                        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 - 100K0
                        $100K - 200K3
                        $200K - 300K10
                        $300K - 400K8
                        $400K - 500K8
                        $500K - 600K2
                        $600K - 700K5
                        $700K - 800K7
                        $800K - 900K6
                        $900K - 1M4
                        $1M - Max7

                        Homes for Sale by Type in Chester, NY

                        Property TypeCount
                        Single Family33
                        Townhouse0
                        Condo10
                        Commercial5
                        Rental25
                        Lots and Land12
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family0
                        Mobile Home0
                        Farms0

                        (Data as of 3/5/2026)

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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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