View 118 Grant Court Chestertown, MD MLS# MDQA2017356
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    OPEN HOUSE: Saturday 5/30 12:00 PM - 2:00 PM
    $457,500
    3

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    2.0

    Baths

    1,664

    Sq.Ft.

    118 Grant Court

    Chestertown, MD

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    View 127 Wood Duck Lane Chestertown, MD MLS# MDQA2017354
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    $138,000
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    2.0

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    1,666

    Sq.Ft.

    127 Wood Duck Lane

    Chestertown, MD

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    View 228 Merganser Drive Chestertown, MD MLS# MDQA2017240
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    $99,000
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    0.0

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    228 Merganser Drive

    Chestertown, MD

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    The time to sell is now! THE TIME TO SELL IS NOW!
    View 109 2Nd Street Chestertown, MD MLS# MDQA2017232
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    $150,000
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    109 2Nd Street

    Chestertown, MD

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    View 215 Fairview Drive Chestertown, MD MLS# MDQA2017090
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    $425,000
    3

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    2.1

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    1,784

    Sq.Ft.

    215 Fairview Drive

    Chestertown, MD

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    View 208 Central Drive Chestertown, MD MLS# MDQA2016836
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      $299,000
      3

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      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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      OPEN HOUSE: Sunday 5/31 12:00 PM - 2:00 PM
      $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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      $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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      View 2032 Pondtown Road Chestertown, MD MLS# MDQA2016688
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      $325,000
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      2.0

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      1,120

      Sq.Ft.

      2032 Pondtown Road

      Chestertown, MD

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

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        2.0

        Baths

        1,271

        Sq.Ft.

        720 Deep Landing Road

        Chestertown, MD

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        View 704 Truslow Road Chestertown, MD MLS# MDQA2016632
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        $440,000
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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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          1 of 56
          $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 72
          $899,500
          4

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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

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            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

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              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
                3

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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
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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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                  1 of 27
                  $299,000
                  3

                  Beds

                  1.0

                  Baths

                  1,408

                  Sq.Ft.

                  154 Longfellow Drive

                  Chestertown, MD

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                  View 204 Double Creek Road Chestertown, MD MLS# MDQA2015996
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                  $598,000
                  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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                    $88,900
                    Studio

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                    0.0

                    Baths

                    East Street

                    Chestertown, MD

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                    About Chestertown

                    Listings in Chestertown, MD

                    22

                    Estimated median home price

                    $322,500
                    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 - 200K3
                    $200K - 300K3
                    $300K - 400K5
                    $400K - 500K4
                    $500K - 600K2
                    $600K - 700K0
                    $700K - 800K0
                    $800K - 900K1
                    $900K - 1M0
                    $1M - Max0

                    Homes for Sale by Type in Chestertown, MD

                    Property TypeCount
                    Single Family16
                    Townhouse0
                    Condo0
                    Commercial0
                    Rental1
                    Lots and Land6
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family0
                    Mobile Home0
                    Farms0

                    (Data as of 5/22/2026)

                    Find Properties in Chestertown, MD

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                    Information deemed reliable but not guaranteed.

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                    Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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