View 204 Double Creek Road Chestertown, MD MLS# MDQA2015996
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$545,000
3

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2.1

Baths

2,927

Sq.Ft.

204 Double Creek Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 240 Merganser Drive Chestertown, MD MLS# MDQA2016900
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$365,000
3

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2.0

Baths

1,120

Sq.Ft.

240 Merganser Drive

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 123 Heath Road Chestertown, MD MLS# MDQA2017994
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$349,000
3

Beds

2.0

Baths

1,792

Sq.Ft.

123 Heath Road

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 217 Edmore Road Chestertown, MD MLS# MDQA2018386
    Save 217 Edmore Road Chestertown, MD MLS# MDQA2018386
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    $345,000
    3

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    1.1

    Baths

    1,398

    Sq.Ft.

    217 Edmore Road

    Chestertown, MD

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    Courtesy of DOUG ASHLEY REALTORS, LLC
    View 222 Dutchess Road Chestertown, MD MLS# MDQA2014830
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      1 of 25
      $320,000
      3

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      1.1

      Baths

      1,096

      Sq.Ft.

      222 Dutchess Road

      Chestertown, MD

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      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 109 Parma Road Chestertown, MD MLS# MDQA2018184
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        OPEN HOUSE: Saturday 9/5 10:00 AM - 12:00 PM
        $315,000
        3

        Beds

        2.0

        Baths

        1,288

        Sq.Ft.

        109 Parma Road

        Chestertown, MD

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        Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
        View 124 Wilton Road Chestertown, MD MLS# MDQA2018272
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        Save 124 Wilton Road Chestertown, MD MLS# MDQA2018272
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        $299,900
        3

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        1.0

        Baths

        1,056

        Sq.Ft.

        124 Wilton Road

        Chestertown, MD

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        Courtesy of DOUG ASHLEY REALTORS, LLC
        View 240 Round Top Road Chestertown, MD MLS# MDQA2018166
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          $295,000
          3

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          2.0

          Baths

          1,132

          Sq.Ft.

          240 Round Top Road

          Chestertown, MD

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          Courtesy of CLARK & CO REALTY, LLC
          View 533 Round Top Road Chestertown, MD MLS# MDQA2018038
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            $225,000
            4

            Beds

            1.1

            Baths

            1,800

            Sq.Ft.

            533 Round Top Road

            Chestertown, MD

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            Courtesy of EXP REALTY, LLC
            View 0 Round Top Road Chestertown, MD MLS# MDQA2016578
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              $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 109 2Nd Street Chestertown, MD MLS# MDQA2017232
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                $135,000
                Studio

                Beds

                0.0

                Baths

                109 2Nd Street

                Chestertown, MD

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                Courtesy of CROSS STREET REALTORS LLC
                View 1906 Pondtown Road Chestertown, MD MLS# MDQA2017476
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                  1 of 4
                  $110,000
                  Studio

                  Beds

                  0.0

                  Baths

                  1906 Pondtown Road

                  Chestertown, MD

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                  Courtesy of KELLER WILLIAMS FLAGSHIP
                  View 233 Merganser Drive Chestertown, MD MLS# MDQA2017912
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                    $60,000
                    Studio

                    Beds

                    0.0

                    Baths

                    233 Merganser Drive

                    Chestertown, MD

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                    Courtesy of LONG & FOSTER REAL ESTATE, INC.
                    View 404 Spring Road Chestertown, MD MLS# MDQA2014990
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                      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

                      15

                      Estimated median home price

                      $299,900
                      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 - 200K3
                      $200K - 300K3
                      $300K - 400K5
                      $400K - 500K0
                      $500K - 600K1
                      $600K - 700K1
                      $700K - 800K0
                      $800K - 900K0
                      $900K - 1M0
                      $1M - Max0

                      Homes for Sale by Type in Chestertown, MD

                      Property TypeCount
                      Single Family10
                      Townhouse0
                      Condo0
                      Commercial0
                      Rental2
                      Lots and Land5
                      Condo/Town/CoOp0
                      CoOp0
                      Multi Family0
                      Mobile Home0
                      Farms0

                      (Data as of 8/25/2026)

                      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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