View 129 Parma Road Chestertown, MD MLS# MDQA2015862
    Save 129 Parma Road Chestertown, MD MLS# MDQA2015862
    1 of 5
    $330,000
    3

    Beds

    2.0

    Baths

    1,170

    Sq.Ft.

    129 Parma Road

    Chestertown, MD

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    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View 104 Iris Road Chestertown, MD MLS# MDQA2015798
    • Recently Listed
    Save 104 Iris Road Chestertown, MD MLS# MDQA2015798
    1 of 36
    $379,000
    3

    Beds

    2.0

    Baths

    1,700

    Sq.Ft.

    104 Iris Road

    Chestertown, MD

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    Courtesy of DOUG ASHLEY REALTORS, LLC
    View 213 Central Drive Chestertown, MD MLS# MDQA2015648
      Save 213 Central Drive Chestertown, MD MLS# MDQA2015648
      1 of 23
      OPEN HOUSE: Sunday 1/18 12:00 PM - 2:00 PM
      $314,900
      3

      Beds

      2.0

      Baths

      1,232

      Sq.Ft.

      213 Central Drive

      Chestertown, MD

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      Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 676 Deep Landing Road Chestertown, MD MLS# MDQA2015466
        Save 676 Deep Landing Road Chestertown, MD MLS# MDQA2015466
        1 of 24
        $315,000
        3

        Beds

        2.1

        Baths

        1,468

        Sq.Ft.

        676 Deep Landing Road

        Chestertown, MD

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        Courtesy of CROSS STREET REALTORS LLC
        View East Street Chestertown, MD MLS# MDQA2015588
          Save East Street Chestertown, MD MLS# MDQA2015588
          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 121 Primrose Road Chestertown, MD MLS# MDQA2015570
            Save 121 Primrose Road Chestertown, MD MLS# MDQA2015570
            1 of 22
            OPEN HOUSE: Sunday 1/18 10:00 AM - 12:00 PM
            $350,000
            3

            Beds

            2.1

            Baths

            2,034

            Sq.Ft.

            121 Primrose Road

            Chestertown, MD

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            Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
            View 127 Wood Duck Lane Chestertown, MD MLS# MDQA2015154
              Save 127 Wood Duck Lane Chestertown, MD MLS# MDQA2015154
              1 of 26
              $215,000
              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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                Courtesy of GUNTHER-MCCLARY REAL ESTATE
                View 108 Primrose Road Chestertown, MD MLS# MDQA2015000
                  Save 108 Primrose Road Chestertown, MD MLS# MDQA2015000
                  1 of 49
                  $375,000
                  3

                  Beds

                  2.0

                  Baths

                  1,722

                  Sq.Ft.

                  108 Primrose Road

                  Chestertown, MD

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                  Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
                  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
                    View 119 Darden Road Chestertown, MD MLS# MDQA2014828
                      Save 119 Darden Road Chestertown, MD MLS# MDQA2014828
                      1 of 2
                      $315,000
                      3

                      Beds

                      2.0

                      Baths

                      1,424

                      Sq.Ft.

                      119 Darden Road

                      Chestertown, MD

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                      Courtesy of COMPASS
                      View 134 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2013988
                        Save 134 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2013988
                        1 of 42
                        $279,000
                        3

                        Beds

                        1.0

                        Baths

                        1,128

                        Sq.Ft.

                        134 Char Nor Manor Boulevard

                        Chestertown, MD

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                        Courtesy of MEREDITH FINE PROPERTIES
                        View 165 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2013956
                        • Virtual Tour
                        Save 165 Char Nor Manor Boulevard Chestertown, MD MLS# MDQA2013956
                        1 of 67
                        $409,900
                        4

                        Beds

                        2.1

                        Baths

                        2,258

                        Sq.Ft.

                        165 Char Nor Manor Boulevard

                        Chestertown, MD

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                        Courtesy of RE/MAX EXECUTIVE
                        View 109 Wilton Road Chestertown, MD MLS# MDQA2011782
                        • Virtual Tour
                        Save 109 Wilton Road Chestertown, MD MLS# MDQA2011782
                        1 of 31
                        $344,900
                        3

                        Beds

                        2.0

                        Baths

                        1,392

                        Sq.Ft.

                        109 Wilton Road

                        Chestertown, MD

                        Bright
                        Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC

                        About Chestertown

                        Listings in Chestertown, MD

                        16

                        Estimated median home price

                        $325,000
                        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 - 100K2
                        $100K - 200K0
                        $200K - 300K2
                        $300K - 400K9
                        $400K - 500K1
                        $500K - 600K1
                        $600K - 700K0
                        $700K - 800K0
                        $800K - 900K0
                        $900K - 1M0
                        $1M - Max1

                        Homes for Sale by Type in Chestertown, MD

                        Property TypeCount
                        Single Family14
                        Townhouse0
                        Condo0
                        Commercial0
                        Rental0
                        Lots and Land2
                        Condo/Town/CoOp0
                        CoOp0
                        Multi Family0
                        Mobile Home0
                        Farms0

                        (Data as of 1/11/2026)

                        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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