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

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    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

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      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 40003 Tippit Road Leonardtown, MD MLS# MDSM2030260
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          $995,000
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          3.0

          Baths

          2,490

          Sq.Ft.

          40003 Tippit Road

          Leonardtown, MD

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          View 40171 Little Woods Lane Leonardtown, MD MLS# MDSM2030192
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            1 of 64
            $875,000
            4

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            2.0

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            2,586

            Sq.Ft.

            40171 Little Woods Lane

            Leonardtown, MD

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            View Ferny Hills Lane Leonardtown, MD MLS# MDSM2030128
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              $840,000
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              Ferny Hills Lane

              Leonardtown, MD

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              View 39577 Potomac Avenue Leonardtown, MD MLS# MDSM2030378
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                $839,900
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                2.1

                Baths

                3,412

                Sq.Ft.

                39577 Potomac Avenue

                Leonardtown, MD

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                View 21130 Someday Farm Lane Leonardtown, MD MLS# MDSM2030588
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                $800,000
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                2.1

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                3,122

                Sq.Ft.

                21130 Someday Farm Lane

                Leonardtown, MD

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                View 39645 Sweetpea Lane Leonardtown, MD MLS# MDSM2031258
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                $799,900
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                39645 Sweetpea Lane

                Leonardtown, MD

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                View 40624 Breton Oaks Lane Leonardtown, MD MLS# MDSM2030230
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                $779,000
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                3.1

                Baths

                2,745

                Sq.Ft.

                40624 Breton Oaks Lane

                Leonardtown, MD

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                View 22393 Saint Clements Avenue Leonardtown, MD MLS# MDSM2029036
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                $774,900
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                2.2

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                2,097

                Sq.Ft.

                22393 Saint Clements Avenue

                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 20752 Penansey Lane Leonardtown, MD MLS# MDSM2029892
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                    $750,000
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                    3.1

                    Baths

                    2,936

                    Sq.Ft.

                    20752 Penansey Lane

                    Leonardtown, MD

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                    View 21390 Little Saint Annes Lane Leonardtown, MD MLS# MDSM2031120
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                      1 of 95
                      $739,500
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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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                        1 of 91
                        $715,000
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                        Beds

                        3.1

                        Baths

                        4,367

                        Sq.Ft.

                        41395 Omaha Court

                        Leonardtown, MD

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                        View 42195 White Point Beach Road Leonardtown, MD MLS# MDSM2030794
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                          1 of 57
                          $699,900
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                          Beds

                          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
                            4

                            Beds

                            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

                              Beds

                              2.1

                              Baths

                              3,098

                              Sq.Ft.

                              41249 Brenda Court

                              Leonardtown, MD

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                              View 23563 Belmar Drive Leonardtown, MD MLS# MDSM2029898
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                                1 of 69
                                $650,000
                                4

                                Beds

                                3.1

                                Baths

                                3,299

                                Sq.Ft.

                                23563 Belmar Drive

                                Leonardtown, MD

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                                About Leonardtown

                                Listings in Leonardtown, MD

                                92

                                Estimated median home price

                                $489,900
                                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 - 300K1
                                $300K - 400K6
                                $400K - 500K32
                                $500K - 600K12
                                $600K - 700K14
                                $700K - 800K9
                                $800K - 900K3
                                $900K - 1M1
                                $1M - Max5

                                Homes for Sale by Type in Leonardtown, MD

                                Property TypeCount
                                Single Family53
                                Townhouse24
                                Condo0
                                Commercial1
                                Rental18
                                Lots and Land14
                                Condo/Town/CoOp0
                                CoOp0
                                Multi Family0
                                Mobile Home0
                                Farms0

                                (Data as of 5/23/2026)

                                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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