View 860 & 870 High Street Chestertown, MD MLS# MDKE2003850
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$2,800,000
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0.0

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16,977

Sq.Ft.

860 & 870 High Street

Chestertown, MD

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Courtesy of TAYLOR PROPERTIES
View 8974 S Bayview Drive Chestertown, MD MLS# MDKE2003854
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$2,395,000
4

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3.1

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3,232

Sq.Ft.

8974 S Bayview Drive

Chestertown, MD

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Courtesy of CROSS STREET REALTORS LLC
View 22900 Handy Point Road Handy Point Road Chestertown, MD MLS# MDKE2003350
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    $1,765,000
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    4,885

    Sq.Ft.

    22900 Handy Point Road Handy Point Road

    Chestertown, MD

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    Courtesy of DAVIS REAL ESTATE, INC.
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 201 N Water Street Chestertown, MD MLS# MDKE2002790
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    $1,725,000
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    5,195

    Sq.Ft.

    201 N Water Street

    Chestertown, MD

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    Courtesy of MARYLAND HERITAGE PROPERTIES
    View Little Harbor Way # 1 Chestertown, MD MLS# MDKE2002724
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    $1,449,000
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    2,315

    Sq.Ft.

    Little Harbor Way # 1

    Chestertown, MD

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    View 22956 Fairgale Farm Lane Chestertown, MD MLS# MDKE2003704
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      $1,360,000
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      6,459

      Sq.Ft.

      22956 Fairgale Farm Lane

      Chestertown, MD

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      Courtesy of DOUG ASHLEY REALTORS, LLC
      View 9545 Chantilly Farm Lane Chestertown, MD MLS# MDKE2003762
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        $1,349,000
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        3.1

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        2,200

        Sq.Ft.

        9545 Chantilly Farm Lane

        Chestertown, MD

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          $1,349,000
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          2,200

          Sq.Ft.

          9545 Chantilly Farm Lane

          Chestertown, MD

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          View 9220 N Bayview Avenue Chestertown, MD MLS# MDKE2003836
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            $1,200,000
            3

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            2.0

            Baths

            2,028

            Sq.Ft.

            9220 N Bayview Avenue

            Chestertown, MD

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            View 131, 133 and 129 Flatland Road Chestertown, MD MLS# MDKE2003342
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            $1,095,000
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            131, 133 and 129 Flatland Road

            Chestertown, MD

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            $1,095,000
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            2.0

            Baths

            4,684

            Sq.Ft.

            131, 133 and 129 Flatland Road

            Chestertown, MD

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            View 226 S Water Street Chestertown, MD MLS# MDKE2001618
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            $995,000
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            226 S Water Street

            Chestertown, MD

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            View 230 S Water Street # 1 Chestertown, MD MLS# MDKE2001598
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            $995,000
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            2,490

            Sq.Ft.

            230 S Water Street # 1

            Chestertown, MD

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            View 7755 Waterview Lane Chestertown, MD MLS# MDKE2003814
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              1 of 65
              $975,000
              4

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              2.1

              Baths

              4,730

              Sq.Ft.

              7755 Waterview Lane

              Chestertown, MD

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              View 228 S Water Street Chestertown, MD MLS# MDKE2001612
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              $950,000
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              228 S Water Street

              Chestertown, MD

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              View Landing Lane # 25 Chestertown, MD MLS# MDKE2002704
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              $949,900
              4

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              3.1

              Baths

              2,784

              Sq.Ft.

              Landing Lane # 25

              Chestertown, MD

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              View 343 Calvert Street Chestertown, MD MLS# MDKE2003750
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                $900,000
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                343 Calvert Street

                Chestertown, MD

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                View 98 Cannon Street Chestertown, MD MLS# MDKE2002356
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                  1 of 22
                  $899,000
                  Studio

                  Beds

                  0.0

                  Baths

                  5,094

                  Sq.Ft.

                  98 Cannon Street

                  Chestertown, MD

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                  View 515 Washington Avenue Chestertown, MD MLS# MDKE2000776
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                    $895,000
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                    42,000

                    Sq.Ft.

                    515 Washington Avenue

                    Chestertown, MD

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                    View Little Harbor Way # 19 Chestertown, MD MLS# MDKE2003932
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                    $864,000
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                    2.1

                    Baths

                    1,964

                    Sq.Ft.

                    Little Harbor Way # 19

                    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

                    90

                    Estimated median home price

                    $309,450
                    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 - 100K32
                    $100K - 200K5
                    $200K - 300K8
                    $300K - 400K7
                    $400K - 500K7
                    $500K - 600K0
                    $600K - 700K3
                    $700K - 800K4
                    $800K - 900K8
                    $900K - 1M5
                    $1M - Max11

                    Homes for Sale by Type in Chestertown, MD

                    Property TypeCount
                    Single Family33
                    Townhouse7
                    Condo4
                    Commercial5
                    Rental13
                    Lots and Land36
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family4
                    Mobile Home0
                    Farms1

                    (Data as of 5/11/2024)

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