View 20753 Chestnut Ridge Drive Leonardtown, MD MLS# MDSM2028218
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    1 of 45
    $574,900
    4

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    2.1

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    2,594

    Sq.Ft.

    20753 Chestnut Ridge Drive

    Leonardtown, MD

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    View 20697 Chingville Road Leonardtown, MD MLS# MDSM2028196
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      1 of 87
      $475,000
      3

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      2.0

      Baths

      2,458

      Sq.Ft.

      20697 Chingville Road

      Leonardtown, MD

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      View Lot 104 - 23695 Dragonfly Lane Leonardtown, MD MLS# MDSM2028144
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      Save Lot 104 - 23695 Dragonfly Lane Leonardtown, MD MLS# MDSM2028144
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      OPEN HOUSE: Friday 1/9 1:00 PM - 4:00 PM
      $449,900
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      Baths

      Lot 104 - 23695 Dragonfly Lane

      Leonardtown, MD

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      The time to sell is now! THE TIME TO SELL IS NOW!
      View lot 106 - 23683 Dragonfly Lane Leonardtown, MD MLS# MDSM2028148
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      OPEN HOUSE: Friday 1/9 1:00 PM - 4:00 PM
      $449,900
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      Baths

      lot 106 - 23683 Dragonfly Lane

      Leonardtown, MD

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      View Lot 105 - 23689 Dragonfly Lane Leonardtown, MD MLS# MDSM2028150
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      OPEN HOUSE: Friday 1/9 1:00 PM - 4:00 PM
      $449,900
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      Baths

      Lot 105 - 23689 Dragonfly Lane

      Leonardtown, MD

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      View 41492 Charismatic Way Leonardtown, MD MLS# MDSM2028074
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      1 of 49
      $639,900
      4

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      3.1

      Baths

      3,322

      Sq.Ft.

      41492 Charismatic Way

      Leonardtown, MD

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      View 40412 B Somerville Lane Leonardtown, MD MLS# MDSM2027980
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        1 of 28
        $149,900
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        0.0

        Baths

        40412 B Somerville Lane

        Leonardtown, MD

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        View 23264 Lindsay Drive Leonardtown, MD MLS# MDSM2027806
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          1 of 59
          $599,000
          3

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          2.0

          Baths

          2,824

          Sq.Ft.

          23264 Lindsay Drive

          Leonardtown, MD

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          View 43018 Bluejay Lane Leonardtown, MD MLS# MDSM2027792
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            1 of 66
            $645,900
            4

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            2.1

            Baths

            2,888

            Sq.Ft.

            43018 Bluejay Lane

            Leonardtown, MD

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            View 21117 Catnip Court Leonardtown, MD MLS# MDSM2027750
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              1 of 49
              $610,000
              5

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              3.1

              Baths

              3,526

              Sq.Ft.

              21117 Catnip Court

              Leonardtown, MD

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              View 43488 Medleys Neck Road Leonardtown, MD MLS# MDSM2027738
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                $215,000
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                0.0

                Baths

                43488 Medleys Neck Road

                Leonardtown, MD

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                View Sunset Drive Leonardtown, MD MLS# MDSM2027604
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                  1 of 1
                  $25,000
                  Studio

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                  0.0

                  Baths

                  Sunset Drive

                  Leonardtown, MD

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                  View 21925 Budds Creek Road Leonardtown, MD MLS# MDSM2027122
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                    1 of 31
                    $465,000
                    3

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                    2.0

                    Baths

                    2,527

                    Sq.Ft.

                    21925 Budds Creek Road

                    Leonardtown, MD

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                    View Lot 103 - 23701 Dragonfly Lane Leonardtown, MD MLS# MDSM2027274
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                    $489,900
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                    Lot 103 - 23701 Dragonfly Lane

                    Leonardtown, MD

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                    View 21920 Newtowne Neck Road Leonardtown, MD MLS# MDSM2027316
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                      1 of 57
                      $510,000
                      4

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                      2.1

                      Baths

                      2,291

                      Sq.Ft.

                      21920 Newtowne Neck Road

                      Leonardtown, MD

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                      View Lot 95 - 23718 Dragonfly Lane Leonardtown, MD MLS# MDSM2027394
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                      $449,900
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                      Lot 95 - 23718 Dragonfly Lane

                      Leonardtown, MD

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                      View Lot 107-23677 Dragonfly Lane Leonardtown, MD MLS# MDSM2027396
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                      1 of 58
                      $479,900
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                      Lot 107-23677 Dragonfly Lane

                      Leonardtown, MD

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                      View 42043 Starlight Drive Leonardtown, MD MLS# MDSM2027150
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                        1 of 50
                        $539,900
                        4

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                        3.1

                        Baths

                        2,472

                        Sq.Ft.

                        42043 Starlight Drive

                        Leonardtown, MD

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                        View 21039 Woodmere Drive Leonardtown, MD MLS# MDSM2027164
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                          1 of 60
                          $580,000
                          5

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                          2.1

                          Baths

                          4,112

                          Sq.Ft.

                          21039 Woodmere Drive

                          Leonardtown, MD

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                          View 41536 Fairwood Court Leonardtown, MD MLS# MDSM2027022
                            Save 41536 Fairwood Court Leonardtown, MD MLS# MDSM2027022
                            1 of 85
                            $569,000
                            4

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                            3.1

                            Baths

                            3,308

                            Sq.Ft.

                            41536 Fairwood Court

                            Leonardtown, MD

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                            About Leonardtown

                            Listings in Leonardtown, MD

                            62

                            Estimated median home price

                            $524,950
                            Leonardtown MD Homes for Sale & Properties

                            Weichert Realtors is one of the nation's leading providers of Leonardtown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Leonardtown, MD.

                            Homes for Sale by Price in Leonardtown, MD

                            PriceCount
                            $0 - 100K3
                            $100K - 200K6
                            $200K - 300K2
                            $300K - 400K1
                            $400K - 500K16
                            $500K - 600K14
                            $600K - 700K12
                            $700K - 800K3
                            $800K - 900K0
                            $900K - 1M0
                            $1M - Max5

                            Homes for Sale by Type in Leonardtown, MD

                            Property TypeCount
                            Single Family39
                            Townhouse10
                            Condo0
                            Commercial2
                            Rental17
                            Lots and Land11
                            Condo/Town/CoOp0
                            CoOp0
                            Multi Family0
                            Mobile Home0
                            Farms0

                            (Data as of 1/3/2026)

                            Find Properties in Leonardtown, MD

                            Leonardtown, MD Information

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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.

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