View 22338 White Oak Road Leonardtown, MD MLS# MDSM2025664
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    1 of 66
    $550,000
    4

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    2.1

    Baths

    2,328

    Sq.Ft.

    22338 White Oak Road

    Leonardtown, MD

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    View 42043 Starlight Drive Leonardtown, MD MLS# MDSM2027150
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      OPEN HOUSE: Friday 1/2 11:00 AM - 1:00 PM
      $539,900
      4

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      3.1

      Baths

      2,472

      Sq.Ft.

      42043 Starlight Drive

      Leonardtown, MD

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      View 41895 Tomey Court Leonardtown, MD MLS# MDSM2028424
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        $529,900
        5

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        3.1

        Baths

        3,482

        Sq.Ft.

        41895 Tomey Court

        Leonardtown, MD

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        The time to sell is now! THE TIME TO SELL IS NOW!
        View 22547 Landing Way Leonardtown, MD MLS# MDSM2028512
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        1 of 46
        $520,000
        3

        Beds

        3.1

        Baths

        2,764

        Sq.Ft.

        22547 Landing Way

        Leonardtown, MD

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        View 20250 Hawks Way Leonardtown, MD MLS# MDSM2028410
        • New Construction
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        1 of 30
        $519,900
        3

        Beds

        2.0

        Baths

        1,557

        Sq.Ft.

        20250 Hawks Way

        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 25365 Point Lookout Road Leonardtown, MD MLS# MDSM2022468
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            1 of 5
            $497,500
            3

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            1.2

            Baths

            2,952

            Sq.Ft.

            25365 Point Lookout Road

            Leonardtown, MD

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            View 25365 Point Lookout Road Leonardtown, MD MLS# MDSM2022480
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              1 of 9
              $497,500
              2,952

              Sq.Ft.

              25365 Point Lookout Road

              Leonardtown, MD

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              View 21738 Pinehurst Court Leonardtown, MD MLS# MDSM2028668
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                $495,000
                4

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                2.1

                Baths

                1,952

                Sq.Ft.

                21738 Pinehurst Court

                Leonardtown, MD

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                View Lot 103 - 23701 Dragonfly Lane Leonardtown, MD MLS# MDSM2027274
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                Save Lot 103 - 23701 Dragonfly Lane Leonardtown, MD MLS# MDSM2027274
                1 of 49
                $489,900
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                Baths

                Lot 103 - 23701 Dragonfly Lane

                Leonardtown, MD

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                View Lot 138- 23671 Dragonfly Lane Leonardtown, MD MLS# MDSM2028534
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                1 of 38
                $487,400
                4

                Beds

                3.1

                Baths

                3,095

                Sq.Ft.

                Lot 138- 23671 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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                Baths

                Lot 107-23677 Dragonfly Lane

                Leonardtown, MD

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                View Lot 108- 23666 Weeping Willow Way Leonardtown, MD MLS# MDSM2028518
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                Save Lot 108- 23666 Weeping Willow Way Leonardtown, MD MLS# MDSM2028518
                1 of 39
                $479,900
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                Baths

                Lot 108- 23666 Weeping Willow Way

                Leonardtown, MD

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                View Lot 137- 23667 Weeping Willow Way Leonardtown, MD MLS# MDSM2028536
                • New Construction with Virtual Tour
                Save Lot 137- 23667 Weeping Willow Way Leonardtown, MD MLS# MDSM2028536
                1 of 42
                $479,900
                4

                Beds

                3.1

                Baths

                2,966

                Sq.Ft.

                Lot 137- 23667 Weeping Willow Way

                Leonardtown, MD

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

                  Beds

                  2.0

                  Baths

                  2,458

                  Sq.Ft.

                  20697 Chingville Road

                  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

                    Beds

                    2.0

                    Baths

                    2,527

                    Sq.Ft.

                    21925 Budds Creek Road

                    Leonardtown, MD

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                    View 41656 Fenwick Street Leonardtown, MD MLS# MDSM2016828
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                    $450,000
                    3,000

                    Sq.Ft.

                    41656 Fenwick Street

                    Leonardtown, MD

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

                    Lot 95 - 23718 Dragonfly Lane

                    Leonardtown, MD

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                    View Lot 104 - 23695 Dragonfly Lane Leonardtown, MD MLS# MDSM2028144
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                    1 of 47
                    OPEN HOUSE: Saturday 1/3 11:00 AM - 2:00 PM
                    $449,900
                    4

                    Beds

                    3.1

                    Baths

                    Lot 104 - 23695 Dragonfly Lane

                    Leonardtown, MD

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                    View lot 106 - 23683 Dragonfly Lane Leonardtown, MD MLS# MDSM2028148
                    • New Construction with Virtual Tour
                    Save lot 106 - 23683 Dragonfly Lane Leonardtown, MD MLS# MDSM2028148
                    1 of 41
                    $449,900
                    4

                    Beds

                    3.1

                    Baths

                    lot 106 - 23683 Dragonfly Lane

                    Leonardtown, MD

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                    About Leonardtown

                    Listings in Leonardtown, MD

                    67

                    Estimated median home price

                    $520,000
                    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 - 100K4
                    $100K - 200K6
                    $200K - 300K3
                    $300K - 400K1
                    $400K - 500K17
                    $500K - 600K14
                    $600K - 700K12
                    $700K - 800K4
                    $800K - 900K1
                    $900K - 1M0
                    $1M - Max5

                    Homes for Sale by Type in Leonardtown, MD

                    Property TypeCount
                    Single Family41
                    Townhouse10
                    Condo0
                    Commercial2
                    Rental16
                    Lots and Land14
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family0
                    Mobile Home0
                    Farms0

                    (Data as of 12/27/2025)

                    Find Properties in Leonardtown, MD

                    Leonardtown, MD Information

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