View Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006302
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$225,000

Haacke Drive Lot 3

Chestertown, MD

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View 10484 Cogar Road Chestertown, MD MLS# MDKE2007056
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    OPEN HOUSE: Sunday 10/18 11:00 AM - 1:00 PM
    $238,000
    3

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    1.0

    Baths

    1,008

    Sq.Ft.

    10484 Cogar Road

    Chestertown, MD

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    View 104 Conley Drive Chestertown, MD MLS# MDKE2006686
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      $239,900
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      Baths

      1,280

      Sq.Ft.

      104 Conley Drive

      Chestertown, MD

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      The time to sell is now! THE TIME TO SELL IS NOW!
      View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290
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        $250,000
        0.0

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        Scheeler Road Lot 2

        Chestertown, MD

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        View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006298
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        $250,000
        37,026

        Sq.Ft.

        Scheeler Road Lot 2

        Chestertown, MD

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        View 115 Chester Arms Drive Chestertown, MD MLS# MDKE2006958
          Save 115 Chester Arms Drive Chestertown, MD MLS# MDKE2006958
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          $259,000
          3

          Beds

          2.0

          Baths

          1,140

          Sq.Ft.

          115 Chester Arms Drive

          Chestertown, MD

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          View 115 Metcalf Road Chestertown, MD MLS# MDKE2006826
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          OPEN HOUSE: Tuesday 10/13 6:00 PM - 7:00 PM
          $259,900
          3

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          1.1

          Baths

          1,280

          Sq.Ft.

          115 Metcalf Road

          Chestertown, MD

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          View 103 Metcalf Road Chestertown, MD MLS# MDKE2007148
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          $259,900
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          1,280

          Sq.Ft.

          103 Metcalf Road

          Chestertown, MD

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          View 121 Metcalf Road Chestertown, MD MLS# MDKE2006678
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          $264,900
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          121 Metcalf Road

          Chestertown, MD

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          View 10540 Tonopah Road Chestertown, MD MLS# MDKE2006880
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            1 of 21
            $269,000
            3

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            2.0

            Baths

            1,404

            Sq.Ft.

            10540 Tonopah Road

            Chestertown, MD

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            View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
              Save 611 Cannon Street Chestertown, MD MLS# MDKE2005906
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              $275,000
              2

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              1.1

              Baths

              920

              Sq.Ft.

              611 Cannon Street

              Chestertown, MD

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              View 956 Washington Avenue Chestertown, MD MLS# MDKE2006394
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              $275,000
              3

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              1.0

              Baths

              1,248

              Sq.Ft.

              956 Washington Avenue

              Chestertown, MD

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              View 104 Acorn Drive Chestertown, MD MLS# MDKE2006668
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                $275,000
                3

                Beds

                2.1

                Baths

                1,900

                Sq.Ft.

                104 Acorn Drive

                Chestertown, MD

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                View 7482 Poplar Avenue Chestertown, MD MLS# MDKE2007042
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                  $275,000
                  3

                  Beds

                  1.0

                  Baths

                  975

                  Sq.Ft.

                  7482 Poplar Avenue

                  Chestertown, MD

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                  View Cannon Street Chestertown, MD MLS# MDKE2006944
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                    $281,000
                    0.0

                    Baths

                    Cannon Street

                    Chestertown, MD

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                    View 104 Lincoln Drive Chestertown, MD MLS# MDKE2007032
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                    $285,000
                    3

                    Beds

                    1.0

                    Baths

                    960

                    Sq.Ft.

                    104 Lincoln Drive

                    Chestertown, MD

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                    View 8732 Elm Road Chestertown, MD MLS# MDKE2007082
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                      $289,000
                      3

                      Beds

                      2.0

                      Baths

                      1,056

                      Sq.Ft.

                      8732 Elm Road

                      Chestertown, MD

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                      View 203 Manor Avenue Chestertown, MD MLS# MDKE2007180
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                        OPEN HOUSE: Saturday 10/17 11:00 AM - 2:00 PM
                        $296,000
                        3

                        Beds

                        1.1

                        Baths

                        1,248

                        Sq.Ft.

                        203 Manor Avenue

                        Chestertown, MD

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                        View 201 N Lynchburg Street # LOTS 4, 5, 6 & 7 Chestertown, MD MLS# MDKE2006846
                          Save 201 N Lynchburg Street # LOTS 4, 5, 6 & 7 Chestertown, MD MLS# MDKE2006846
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                          $300,000
                          0.0

                          Baths

                          201 N Lynchburg Street # LOTS 4, 5, 6 & 7

                          Chestertown, MD

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                          View 7464 Shortall Street Chestertown, MD MLS# MDKE2006988
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                          $304,000
                          3

                          Beds

                          2.0

                          Baths

                          1,232

                          Sq.Ft.

                          7464 Shortall Street

                          Chestertown, MD

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                          About Chestertown

                          Home of George Washington College, Chestertown is the center of amenities and the hub of life in Kent County.  Located on the banks of the Chester River, Chestertown began as a prosperous shipbuilding, trade and government center during the colonial movement and still maintains the state’s oldest records.  The popular autumn Candlelight Walking Tour offers a glimpse into many of the spectacular homes built by wealthy merchants of the 18th and 19th centuries.  Quaint red-brick sidewalks and broad, shaded streets form an idyllic backdrop for specialty shops, galleries and eateries.  On cool summer evenings, residents can relax to the strains of concerts held around the antique fountain in the town square.  Lovely homes, a stimulating college-town atmosphere and community pride make Chestertown the ideal place to call home. 

                          Listings in Chestertown, MD

                          129

                          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 - 100K34
                          $100K - 200K4
                          $200K - 300K20
                          $300K - 400K21
                          $400K - 500K9
                          $500K - 600K2
                          $600K - 700K6
                          $700K - 800K10
                          $800K - 900K7
                          $900K - 1M0
                          $1M - Max16

                          Homes for Sale by Type in Chestertown, MD

                          Property TypeCount
                          Single Family51
                          Townhouse7
                          Condo15
                          Commercial12
                          Rental9
                          Lots and Land43
                          Condo/Town/CoOp0
                          CoOp0
                          Multi Family0
                          Mobile Home0
                          Farms1

                          (Data as of 10/12/2026)

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