View 208 Central Drive Chestertown, MD MLS# MDQA2016836
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$315,000
3

Beds

1.0

Baths

1,120

Sq.Ft.

208 Central Drive

Chestertown, MD

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View 240 Merganser Drive Chestertown, MD MLS# MDQA2016900
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    $425,000
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    2.0

    Baths

    1,120

    Sq.Ft.

    240 Merganser Drive

    Chestertown, MD

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    View 126 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2016812
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      OPEN HOUSE: Friday 4/24 5:00 PM - 7:00 PM
      $349,000
      3

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      2.0

      Baths

      1,304

      Sq.Ft.

      126 Char Nor Manor Boulevard

      Chestertown, MD

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      The time to sell is now! THE TIME TO SELL IS NOW!
      View 136 Hilltop Drive Chestertown, MD MLS# MDQA2016782
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      $366,000
      3

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      2.0

      Baths

      1,432

      Sq.Ft.

      136 Hilltop Drive

      Chestertown, MD

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      View 107 Longfellow Drive Chestertown, MD MLS# MDQA2016720
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      $295,000
      3

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      Baths

      107 Longfellow Drive

      Chestertown, MD

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      View 720 Deep Landing Road Chestertown, MD MLS# MDQA2016758
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        $369,999
        3

        Beds

        2.0

        Baths

        1,271

        Sq.Ft.

        720 Deep Landing Road

        Chestertown, MD

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        View 144 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2016682
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        $55,000
        Studio

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        144 Char Nor Manor Boulevard

        Chestertown, MD

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        View 704 Truslow Road Chestertown, MD MLS# MDQA2016632
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        $440,000
        3

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        2.1

        Baths

        2,060

        Sq.Ft.

        704 Truslow Road

        Chestertown, MD

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        View 101 Coleman Drive Chestertown, MD MLS# MDQA2016624
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          OPEN HOUSE: Saturday 4/25 11:00 AM - 2:00 PM
          $524,900
          3

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          2.1

          Baths

          2,268

          Sq.Ft.

          101 Coleman Drive

          Chestertown, MD

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          View 205 River Road Chestertown, MD MLS# MDQA2016560
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          1 of 15
          $949,000
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          2.1

          Baths

          2,877

          Sq.Ft.

          205 River Road

          Chestertown, MD

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          View 0 Round Top Road Chestertown, MD MLS# MDQA2016578
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            $200,000
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            0.0

            Baths

            0 Round Top Road

            Chestertown, MD

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            View 206 Burchard Sawmill Road Chestertown, MD MLS# MDQA2016510
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              $29,000
              Studio

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              0.0

              Baths

              206 Burchard Sawmill Road

              Chestertown, MD

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              View 113 Pear Tree Point Road Chestertown, MD MLS# MDQA2016478
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              $250,000
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              1.0

              Baths

              1,296

              Sq.Ft.

              113 Pear Tree Point Road

              Chestertown, MD

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              View 109 Wilton Road Chestertown, MD MLS# MDQA2016312
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              $344,900
              3

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              2.0

              Baths

              1,392

              Sq.Ft.

              109 Wilton Road

              Chestertown, MD

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              View 154 Longfellow Drive Chestertown, MD MLS# MDQA2016250
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                $299,000
                3

                Beds

                1.0

                Baths

                1,408

                Sq.Ft.

                154 Longfellow Drive

                Chestertown, MD

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                View 101 Pine Tree Road Chestertown, MD MLS# MDQA2016188
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                  $480,000
                  4

                  Beds

                  2.0

                  Baths

                  1,848

                  Sq.Ft.

                  101 Pine Tree Road

                  Chestertown, MD

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                  View 204 Double Creek Road Chestertown, MD MLS# MDQA2015996
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                  $612,000
                  3

                  Beds

                  2.1

                  Baths

                  2,927

                  Sq.Ft.

                  204 Double Creek Road

                  Chestertown, MD

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                  View East Street Chestertown, MD MLS# MDQA2015588
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                    1 of 8
                    $88,900
                    Studio

                    Beds

                    0.0

                    Baths

                    East Street

                    Chestertown, MD

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                    View 127 Wood Duck Lane Chestertown, MD MLS# MDQA2015154
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                      1 of 26
                      $185,000
                      3

                      Beds

                      2.0

                      Baths

                      1,666

                      Sq.Ft.

                      127 Wood Duck Lane

                      Chestertown, MD

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                      View 222 Dutchess Road Chestertown, MD MLS# MDQA2014830
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                        $320,000
                        3

                        Beds

                        1.1

                        Baths

                        1,096

                        Sq.Ft.

                        222 Dutchess Road

                        Chestertown, MD

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                        About Chestertown

                        Listings in Chestertown, MD

                        21

                        Estimated median home price

                        $320,000
                        Chestertown MD Homes for Sale & Properties

                        Weichert Realtors is one of the nation's leading providers of Chestertown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, MD.

                        Homes for Sale by Price in Chestertown, MD

                        PriceCount
                        $0 - 100K4
                        $100K - 200K2
                        $200K - 300K3
                        $300K - 400K6
                        $400K - 500K3
                        $500K - 600K1
                        $600K - 700K1
                        $700K - 800K0
                        $800K - 900K0
                        $900K - 1M1
                        $1M - Max0

                        Homes for Sale by Type in Chestertown, MD

                        Property TypeCount
                        Single Family16
                        Townhouse0
                        Condo0
                        Commercial0
                        Rental2
                        Lots and Land5
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family0
                        Mobile Home0
                        Farms0

                        (Data as of 4/19/2026)

                        Find Properties in Chestertown, MD

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                        Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

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