View 126 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2016812
    Save 126 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2016812
    1 of 4
    $349,000
    3

    Beds

    2.0

    Baths

    1,304

    Sq.Ft.

    126 Char Nor Manor Boulevard

    Chestertown, MD

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    Courtesy of RE/MAX EXECUTIVE
    View 136 Hilltop Drive Chestertown, MD MLS# MDQA2016782
      Save 136 Hilltop Drive Chestertown, MD MLS# MDQA2016782
      $366,000
      Studio

      Beds

      0.0

      Baths

      1,432

      Sq.Ft.

      136 Hilltop Drive

      Chestertown, MD

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      Courtesy of NORTHROP REALTY
      View 107 Longfellow Drive Chestertown, MD MLS# MDQA2016720
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      1 of 37
      $295,000
      3

      Beds

      1.0

      Baths

      107 Longfellow Drive

      Chestertown, MD

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      Courtesy of DOUG ASHLEY REALTORS, LLC
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 720 Deep Landing Road Chestertown, MD MLS# MDQA2016758
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      1 of 42
      $369,999
      3

      Beds

      2.0

      Baths

      1,271

      Sq.Ft.

      720 Deep Landing Road

      Chestertown, MD

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      Courtesy of COLDWELL BANKER WATERMAN REALTY
      View 144 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2016682
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      $55,000
      Studio

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      0.0

      Baths

      144 Char Nor Manor Boulevard

      Chestertown, MD

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      Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
      View 2032 Pondtown Road Chestertown, MD MLS# MDQA2016688
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      1 of 32
      $325,000
      3

      Beds

      2.0

      Baths

      1,120

      Sq.Ft.

      2032 Pondtown Road

      Chestertown, MD

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      Courtesy of NORTHROP REALTY
      View 0 Round Top Road Chestertown, MD MLS# MDQA2016578
        Save 0 Round Top Road Chestertown, MD MLS# MDQA2016578
        1 of 23
        $200,000
        Studio

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        0.0

        Baths

        0 Round Top Road

        Chestertown, MD

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        Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
        View 206 Burchard Sawmill Road Chestertown, MD MLS# MDQA2016510
          Save 206 Burchard Sawmill Road Chestertown, MD MLS# MDQA2016510
          1 of 2
          $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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          1 of 1
          $250,000
          3

          Beds

          1.0

          Baths

          1,296

          Sq.Ft.

          113 Pear Tree Point Road

          Chestertown, MD

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          Courtesy of DOUG ASHLEY REALTORS, LLC
          View 513 Round Top Road Chestertown, MD MLS# MDQA2016458
            Save 513 Round Top Road Chestertown, MD MLS# MDQA2016458
            1 of 18
            $225,000
            4

            Beds

            1.0

            Baths

            1,248

            Sq.Ft.

            513 Round Top Road

            Chestertown, MD

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            Courtesy of CUMMINGS & CO. REALTORS
            View 109 Wilton Road Chestertown, MD MLS# MDQA2016312
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            1 of 31
            $344,900
            3

            Beds

            2.0

            Baths

            1,392

            Sq.Ft.

            109 Wilton Road

            Chestertown, MD

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            Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
            View 154 Longfellow Drive Chestertown, MD MLS# MDQA2016250
              Save 154 Longfellow Drive Chestertown, MD MLS# MDQA2016250
              1 of 27
              $299,000
              3

              Beds

              1.0

              Baths

              1,408

              Sq.Ft.

              154 Longfellow Drive

              Chestertown, MD

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              Courtesy of CROSS STREET REALTORS LLC
              View 148 Step Road Chestertown, MD MLS# MDQA2016258
                Save 148 Step Road Chestertown, MD MLS# MDQA2016258
                1 of 46
                $369,000
                4

                Beds

                2.0

                Baths

                1,400

                Sq.Ft.

                148 Step Road

                Chestertown, MD

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                Courtesy of ANNE ARUNDEL PROPERTIES, INC.
                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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                  Courtesy of SELECT LAND & HOMES, LLC
                  View 127 Wood Duck Lane Chestertown, MD MLS# MDQA2015154
                    Save 127 Wood Duck Lane Chestertown, MD MLS# MDQA2015154
                    1 of 26
                    $185,000
                    3

                    Beds

                    2.0

                    Baths

                    1,666

                    Sq.Ft.

                    127 Wood Duck Lane

                    Chestertown, MD

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                    Courtesy of RE/MAX POINT REALTY
                    View 222 Dutchess Road Chestertown, MD MLS# MDQA2014830
                      Save 222 Dutchess Road Chestertown, MD MLS# MDQA2014830
                      1 of 24
                      $320,000
                      3

                      Beds

                      1.1

                      Baths

                      1,096

                      Sq.Ft.

                      222 Dutchess Road

                      Chestertown, MD

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                      View 404 Spring Road Chestertown, MD MLS# MDQA2014990
                        Save 404 Spring Road Chestertown, MD MLS# MDQA2014990
                        1 of 11
                        $19,500
                        Studio

                        Beds

                        0.0

                        Baths

                        404 Spring Road

                        Chestertown, MD

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                        Courtesy of THE PARKER GROUP

                        About Chestertown

                        Listings in Chestertown, MD

                        24

                        Estimated median home price

                        $334,950
                        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 - 300K4
                        $300K - 400K7
                        $400K - 500K3
                        $500K - 600K2
                        $600K - 700K1
                        $700K - 800K0
                        $800K - 900K0
                        $900K - 1M1
                        $1M - Max0

                        Homes for Sale by Type in Chestertown, MD

                        Property TypeCount
                        Single Family19
                        Townhouse0
                        Condo0
                        Commercial0
                        Rental1
                        Lots and Land5
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family0
                        Mobile Home0
                        Farms0

                        (Data as of 4/11/2026)

                        Find Properties in Chestertown, MD

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                        Information deemed reliable but not guaranteed.

                        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.

                        Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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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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