View 42520 Riverwinds Drive Leonardtown, MD MLS# MDSM2003476
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    $1,999,999
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    2.0

    Baths

    2,744

    Sq.Ft.

    42520 Riverwinds Drive

    Leonardtown, MD

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    View Bayside Road Leonardtown, MD MLS# MDSM2021304
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      $1,750,000
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      2.0

      Baths

      2,130

      Sq.Ft.

      Bayside Road

      Leonardtown, MD

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      View 25845 Point Lookout Road Leonardtown, MD MLS# MDSM2020046
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        $1,740,000
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        25845 Point Lookout Road

        Leonardtown, MD

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        The time to sell is now! THE TIME TO SELL IS NOW!
        View 22164 Miller Court Leonardtown, MD MLS# MDSM2028922
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          $975,000
          4

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          3.0

          Baths

          2,700

          Sq.Ft.

          22164 Miller Court

          Leonardtown, MD

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          View 41832 Foxwell Point Lane Leonardtown, MD MLS# MDSM2027714
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            $800,000
            3

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            2.2

            Baths

            3,683

            Sq.Ft.

            41832 Foxwell Point Lane

            Leonardtown, MD

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            View 44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338
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              $772,000
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              4.1

              Baths

              3,000

              Sq.Ft.

              44798 Medleys Neck Road

              Leonardtown, MD

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              View 41810 Chelsey Faye Lane Leonardtown, MD MLS# MDSM2021276
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              $720,000
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              2.2

              Baths

              2,650

              Sq.Ft.

              41810 Chelsey Faye Lane

              Leonardtown, MD

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              View 42975 Baywood Place Leonardtown, MD MLS# MDSM2028350
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                $699,900
                4

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                2.1

                Baths

                3,372

                Sq.Ft.

                42975 Baywood Place

                Leonardtown, MD

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                View 21345 Fairwood Court Leonardtown, MD MLS# MDSM2028586
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                  OPEN HOUSE: Saturday 1/17 2:00 PM - 4:00 PM
                  $699,900
                  5

                  Beds

                  3.1

                  Baths

                  4,080

                  Sq.Ft.

                  21345 Fairwood Court

                  Leonardtown, MD

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                  View 40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2027068
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                    $679,900
                    2

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                    2.1

                    Baths

                    2,040

                    Sq.Ft.

                    40461 Old Breton Beach Road

                    Leonardtown, MD

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                    View 18937 Hodges Lane Leonardtown, MD MLS# MDSM2023654
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                      $659,000
                      3

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                      2.0

                      Baths

                      1,834

                      Sq.Ft.

                      18937 Hodges Lane

                      Leonardtown, MD

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                      View 23581 Gallent Fox Way Leonardtown, MD MLS# MDSM2028276
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                      $645,900
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                      3.1

                      Baths

                      3,736

                      Sq.Ft.

                      23581 Gallent Fox Way

                      Leonardtown, MD

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                      View 23773 Meredith Court Leonardtown, MD MLS# MDSM2022554
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                      OPEN HOUSE: Sunday 1/18 11:00 AM - 2:00 PM
                      $640,000
                      3

                      Beds

                      2.1

                      Baths

                      3,478

                      Sq.Ft.

                      23773 Meredith Court

                      Leonardtown, MD

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                      View 43018 Bluejay Lane Leonardtown, MD MLS# MDSM2027792
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                        $640,000
                        4

                        Beds

                        2.1

                        Baths

                        2,888

                        Sq.Ft.

                        43018 Bluejay Lane

                        Leonardtown, MD

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                        View 41430 Challedon Way Leonardtown, MD MLS# MDSM2028266
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                        1 of 79
                        $639,000
                        5

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                        3.1

                        Baths

                        4,500

                        Sq.Ft.

                        41430 Challedon Way

                        Leonardtown, MD

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                        View 22113 Philip Drive Leonardtown, MD MLS# MDSM2017056
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                        1 of 85
                        $630,000
                        4

                        Beds

                        3.1

                        Baths

                        3,295

                        Sq.Ft.

                        22113 Philip Drive

                        Leonardtown, MD

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                        View 40855 Spring House Lane Leonardtown, MD MLS# MDSM2028400
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                        $624,900
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                        Beds

                        3.0

                        Baths

                        3,464

                        Sq.Ft.

                        40855 Spring House Lane

                        Leonardtown, MD

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                        View 22615 Washington Street Leonardtown, MD MLS# MDSM2028632
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                          1 of 4
                          $599,950
                          Studio

                          Beds

                          0.0

                          Baths

                          1,691

                          Sq.Ft.

                          22615 Washington Street

                          Leonardtown, MD

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                          View 20260 Hawks Way Leonardtown, MD MLS# MDSM2028700
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                          1 of 29
                          $599,900
                          4

                          Beds

                          2.1

                          Baths

                          2,500

                          Sq.Ft.

                          20260 Hawks Way

                          Leonardtown, MD

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

                            Beds

                            2.0

                            Baths

                            2,824

                            Sq.Ft.

                            23264 Lindsay Drive

                            Leonardtown, MD

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                            About Leonardtown

                            Listings in Leonardtown, MD

                            64

                            Estimated median home price

                            $514,950
                            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 - 200K8
                            $200K - 300K1
                            $300K - 400K1
                            $400K - 500K18
                            $500K - 600K14
                            $600K - 700K11
                            $700K - 800K3
                            $800K - 900K0
                            $900K - 1M0
                            $1M - Max5

                            Homes for Sale by Type in Leonardtown, MD

                            Property TypeCount
                            Single Family39
                            Townhouse11
                            Condo0
                            Commercial2
                            Rental13
                            Lots and Land12
                            Condo/Town/CoOp0
                            CoOp0
                            Multi Family0
                            Mobile Home0
                            Farms0

                            (Data as of 1/16/2026)

                            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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