View 42032 Starlight Drive Leonardtown, MD MLS# MDSM2030894
    Save 42032 Starlight Drive Leonardtown, MD MLS# MDSM2030894
    1 of 57
    $653,000
    5

    Beds

    3.1

    Baths

    4,340

    Sq.Ft.

    42032 Starlight Drive

    Leonardtown, MD

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    Courtesy of CENTURY 21 NEW MILLENNIUM
    View Lot 144 - 23635 Dragonfly Lane Leonardtown, MD MLS# MDSM2030872
    • New Construction with Virtual Tour
    Save Lot 144 - 23635 Dragonfly Lane Leonardtown, MD MLS# MDSM2030872
    1 of 45
    $449,900
    4

    Beds

    3.1

    Baths

    2,604

    Sq.Ft.

    Lot 144 - 23635 Dragonfly Lane

    Leonardtown, MD

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    Courtesy of RE/MAX ONE
    View Lot 115 - 23708 Weeping Willow Way Leonardtown, MD MLS# MDSM2030874
    • New Construction with Virtual Tour
    Save Lot 115 - 23708 Weeping Willow Way Leonardtown, MD MLS# MDSM2030874
    1 of 45
    $449,900
    4

    Beds

    3.1

    Baths

    Lot 115 - 23708 Weeping Willow Way

    Leonardtown, MD

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    Courtesy of RE/MAX ONE
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 42195 White Point Beach Road Leonardtown, MD MLS# MDSM2030794
      Save 42195 White Point Beach Road Leonardtown, MD MLS# MDSM2030794
      1 of 57
      $699,900
      3

      Beds

      2.0

      Baths

      1,636

      Sq.Ft.

      42195 White Point Beach Road

      Leonardtown, MD

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      Courtesy of FRANZEN REALTORS, INC.
      View 40704 Chance Way Leonardtown, MD MLS# MDSM2030700
        Save 40704 Chance Way Leonardtown, MD MLS# MDSM2030700
        1 of 89
        $599,900
        4

        Beds

        2.1

        Baths

        3,300

        Sq.Ft.

        40704 Chance Way

        Leonardtown, MD

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        Courtesy of CENTURY 21 REDWOOD REALTY
        View 41708 Fenwick Street Leonardtown, MD MLS# MDSM2030598
          Save 41708 Fenwick Street Leonardtown, MD MLS# MDSM2030598
          1 of 22
          $300,000
          Studio

          Beds

          0.0

          Baths

          41708 Fenwick Street

          Leonardtown, MD

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          Courtesy of REDFIN CORP
          View 40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470
            Save 40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470
            1 of 42
            $650,000
            2

            Beds

            2.1

            Baths

            2,040

            Sq.Ft.

            40461 Old Breton Beach Road

            Leonardtown, MD

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            Courtesy of THE SOUTHSIDE GROUP REAL ESTATE
            View 41620 Church Street Leonardtown, MD MLS# MDSM2030446
              Save 41620 Church Street Leonardtown, MD MLS# MDSM2030446
              1 of 70
              $399,000
              3

              Beds

              2.0

              Baths

              1,728

              Sq.Ft.

              41620 Church Street

              Leonardtown, MD

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              Courtesy of EVERGREEN PROPERTIES
              View Lot 111 - 23684 Weeping Willow Way Leonardtown, MD MLS# MDSM2030402
              • New Construction with Virtual Tour
              Save Lot 111 - 23684 Weeping Willow Way Leonardtown, MD MLS# MDSM2030402
              1 of 43
              $449,900
              4

              Beds

              3.1

              Baths

              2,554

              Sq.Ft.

              Lot 111 - 23684 Weeping Willow Way

              Leonardtown, MD

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              Courtesy of RE/MAX ONE
              View Lot 142 - 23647 Dragonfly Lane Leonardtown, MD MLS# MDSM2030268
              • New Construction with Virtual Tour
              Save Lot 142 - 23647 Dragonfly Lane Leonardtown, MD MLS# MDSM2030268
              1 of 46
              $489,900
              4

              Beds

              3.1

              Baths

              3,095

              Sq.Ft.

              Lot 142 - 23647 Dragonfly Lane

              Leonardtown, MD

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              Courtesy of RE/MAX ONE
              View Lot 141 - 23653 Dragonfly Lane Leonardtown, MD MLS# MDSM2030224
              • New Construction with Virtual Tour
              Save Lot 141 - 23653 Dragonfly Lane Leonardtown, MD MLS# MDSM2030224
              1 of 41
              $479,900
              4

              Beds

              3.1

              Baths

              Lot 141 - 23653 Dragonfly Lane

              Leonardtown, MD

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              Courtesy of RE/MAX ONE
              View 22281 Nomoni Street Leonardtown, MD MLS# MDSM2030234
                Save 22281 Nomoni Street Leonardtown, MD MLS# MDSM2030234
                1 of 42
                $355,000
                3

                Beds

                2.0

                Baths

                1,152

                Sq.Ft.

                22281 Nomoni Street

                Leonardtown, MD

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                Courtesy of COLDWELL BANKER PREMIER
                View 18866 Russell Road Leonardtown, MD MLS# MDSM2030238
                  Save 18866 Russell Road Leonardtown, MD MLS# MDSM2030238
                  1 of 3
                  $450,000
                  3

                  Beds

                  2.0

                  Baths

                  1,128

                  Sq.Ft.

                  18866 Russell Road

                  Leonardtown, MD

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                  Courtesy of KW METRO CENTER
                  View Lot 128 - 23721 Weeping Willow Way Leonardtown, MD MLS# MDSM2029480
                  • New Construction with Virtual Tour
                  Save Lot 128 - 23721 Weeping Willow Way Leonardtown, MD MLS# MDSM2029480
                  1 of 41
                  $479,900
                  4

                  Beds

                  3.1

                  Baths

                  2,966

                  Sq.Ft.

                  Lot 128 - 23721 Weeping Willow Way

                  Leonardtown, MD

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                  Courtesy of RE/MAX ONE
                  View Lot 135 - 23679 Weeping Willow Way Leonardtown, MD MLS# MDSM2030032
                  • New Construction with Virtual Tour
                  Save Lot 135 - 23679 Weeping Willow Way Leonardtown, MD MLS# MDSM2030032
                  1 of 50
                  $449,900
                  4

                  Beds

                  3.1

                  Baths

                  2,604

                  Sq.Ft.

                  Lot 135 - 23679 Weeping Willow Way

                  Leonardtown, MD

                  Bright
                  Courtesy of RE/MAX ONE
                  View Lot 132 - 23697 Weeping Willow Way Leonardtown, MD MLS# MDSM2029994
                  • New Construction with Virtual Tour
                  Save Lot 132 - 23697 Weeping Willow Way Leonardtown, MD MLS# MDSM2029994
                  1 of 46
                  $489,900
                  4

                  Beds

                  3.1

                  Baths

                  3,095

                  Sq.Ft.

                  Lot 132 - 23697 Weeping Willow Way

                  Leonardtown, MD

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                  Courtesy of RE/MAX ONE
                  View 41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722
                  • Virtual Tour
                  Save 41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722
                  1 of 57
                  $610,000
                  5

                  Beds

                  4.0

                  Baths

                  3,724

                  Sq.Ft.

                  41377 Doctors Crossing Road

                  Leonardtown, MD

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                  Courtesy of KELLER WILLIAMS REALTY/LEE BEAVER & ASSOC.
                  View 20798 Waterside Drive Leonardtown, MD MLS# MDSM2029666
                    Save 20798 Waterside Drive Leonardtown, MD MLS# MDSM2029666
                    1 of 33
                    $450,000
                    2

                    Beds

                    1.0

                    Baths

                    1,018

                    Sq.Ft.

                    20798 Waterside Drive

                    Leonardtown, MD

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                    Courtesy of RE/MAX ONE
                    View Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488
                    • New Construction with Virtual Tour
                    Save Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488
                    1 of 40
                    $449,900
                    4

                    Beds

                    3.1

                    Baths

                    Lot 99 - 23725 Dragonfly Lane

                    Leonardtown, MD

                    Bright
                    Courtesy of RE/MAX ONE
                    View Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218
                    • New Construction with Virtual Tour
                    Save Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218
                    1 of 47
                    $489,900
                    4

                    Beds

                    3.1

                    Baths

                    3,095

                    Sq.Ft.

                    Lot 117 - 23720 Weeping Willow Way

                    Leonardtown, MD

                    Bright
                    Courtesy of RE/MAX ONE

                    About Leonardtown

                    Listings in Leonardtown, MD

                    84

                    Estimated median home price

                    $488,650
                    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 - 300K2
                    $300K - 400K6
                    $400K - 500K31
                    $500K - 600K9
                    $600K - 700K14
                    $700K - 800K7
                    $800K - 900K2
                    $900K - 1M0
                    $1M - Max6

                    Homes for Sale by Type in Leonardtown, MD

                    Property TypeCount
                    Single Family45
                    Townhouse25
                    Condo0
                    Commercial1
                    Rental20
                    Lots and Land13
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family0
                    Mobile Home0
                    Farms0

                    (Data as of 6/23/2026)

                    Find Properties in Leonardtown, MD

                    Leonardtown, MD Information

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