View 21390 Little Saint Annes Lane Leonardtown, MD MLS# MDSM2031120
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    1 of 95
    $739,500
    4

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    3.1

    Baths

    3,500

    Sq.Ft.

    21390 Little Saint Annes Lane

    Leonardtown, MD

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    View 41655 Church Street Leonardtown, MD MLS# MDSM2029620
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      $725,000
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      2.0

      Baths

      2,834

      Sq.Ft.

      41655 Church Street

      Leonardtown, MD

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      View 41395 Omaha Court Leonardtown, MD MLS# MDSM2031298
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        $715,000
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        3.1

        Baths

        4,367

        Sq.Ft.

        41395 Omaha Court

        Leonardtown, MD

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        The time to sell is now! THE TIME TO SELL IS NOW!
        View 42195 White Point Beach Road Leonardtown, MD MLS# MDSM2030794
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          1 of 57
          $699,900
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          2.0

          Baths

          1,636

          Sq.Ft.

          42195 White Point Beach Road

          Leonardtown, MD

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          View 23592 Belmar Drive Leonardtown, MD MLS# MDSM2030098
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            1 of 63
            $680,000
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            2.1

            Baths

            3,728

            Sq.Ft.

            23592 Belmar Drive

            Leonardtown, MD

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            View 41249 Brenda Court Leonardtown, MD MLS# MDSM2030594
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              1 of 79
              $669,900
              3

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              2.1

              Baths

              3,098

              Sq.Ft.

              41249 Brenda Court

              Leonardtown, MD

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              View 42032 Starlight Drive Leonardtown, MD MLS# MDSM2030894
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                $653,000
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                3.1

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                4,340

                Sq.Ft.

                42032 Starlight Drive

                Leonardtown, MD

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                View 40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470
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                  $650,000
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                  2.1

                  Baths

                  2,040

                  Sq.Ft.

                  40461 Old Breton Beach Road

                  Leonardtown, MD

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                  View 23642 Hansel Court Leonardtown, MD MLS# MDSM2031224
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                    1 of 74
                    $649,900
                    4

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                    3.1

                    Baths

                    3,726

                    Sq.Ft.

                    23642 Hansel Court

                    Leonardtown, MD

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                    View 23773 Meredith Court Leonardtown, MD MLS# MDSM2022554
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                    1 of 91
                    $640,000
                    6

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                    Baths

                    3,478

                    Sq.Ft.

                    23773 Meredith Court

                    Leonardtown, MD

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                    View 23621 Margrave Drive Leonardtown, MD MLS# MDSM2030144
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                      1 of 49
                      $639,000
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                      Baths

                      3,664

                      Sq.Ft.

                      23621 Margrave Drive

                      Leonardtown, MD

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                      View 41585 Austin Court Leonardtown, MD MLS# MDSM2030616
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                      1 of 64
                      $635,000
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                      3.0

                      Baths

                      3,030

                      Sq.Ft.

                      41585 Austin Court

                      Leonardtown, MD

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

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                      3.1

                      Baths

                      3,295

                      Sq.Ft.

                      22113 Philip Drive

                      Leonardtown, MD

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                      View 43430 Browns Lane Leonardtown, MD MLS# MDSM2031286
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                      1 of 72
                      $605,000
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                      3.2

                      Baths

                      2,756

                      Sq.Ft.

                      43430 Browns Lane

                      Leonardtown, MD

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

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                        0.0

                        Baths

                        1,691

                        Sq.Ft.

                        22615 Washington Street

                        Leonardtown, MD

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                        View 40704 Chance Way Leonardtown, MD MLS# MDSM2030700
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                          1 of 89
                          $599,900
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                          Beds

                          2.1

                          Baths

                          3,300

                          Sq.Ft.

                          40704 Chance 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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                            View 41482 Pensive Street Leonardtown, MD MLS# MDSM2030772
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                              1 of 75
                              $574,900
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                              3.1

                              Baths

                              4,300

                              Sq.Ft.

                              41482 Pensive Street

                              Leonardtown, MD

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                              View 20260 Hawks Way Leonardtown, MD MLS# MDSM2030406
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                              1 of 45
                              $569,900
                              4

                              Beds

                              2.1

                              Baths

                              2,500

                              Sq.Ft.

                              20260 Hawks Way

                              Leonardtown, MD

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

                                84

                                Estimated median home price

                                $486,200
                                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 - 100K2
                                $100K - 200K5
                                $200K - 300K1
                                $300K - 400K4
                                $400K - 500K35
                                $500K - 600K12
                                $600K - 700K11
                                $700K - 800K7
                                $800K - 900K2
                                $900K - 1M0
                                $1M - Max5

                                Homes for Sale by Type in Leonardtown, MD

                                Property TypeCount
                                Single Family45
                                Townhouse25
                                Condo0
                                Commercial1
                                Rental16
                                Lots and Land13
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family0
                                Mobile Home0
                                Farms0

                                (Data as of 6/1/2026)

                                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.

                                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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