View 23299 Jenifer Court Leonardtown, MD MLS# MDSM2029912
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    $550,000
    5

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    3.0

    Baths

    3,482

    Sq.Ft.

    23299 Jenifer Court

    Leonardtown, MD

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    View 44731 Blake Creek Road Leonardtown, MD MLS# MDSM2029840
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      $365,000
      3

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      2.0

      Baths

      1,644

      Sq.Ft.

      44731 Blake Creek Road

      Leonardtown, MD

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      View 41488 Pensive Street Leonardtown, MD MLS# MDSM2029900
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      1 of 74
      $680,000
      5

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      3.1

      Baths

      3,992

      Sq.Ft.

      41488 Pensive Street

      Leonardtown, MD

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      The time to sell is now! THE TIME TO SELL IS NOW!
      View 0 Saint Andrews Church Rd Leonardtown, MD MLS# MDSM2029792
        Save 0 Saint Andrews Church Rd Leonardtown, MD MLS# MDSM2029792
        1 of 34
        $98,900
        Studio

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        0.0

        Baths

        0 Saint Andrews Church Rd

        Leonardtown, MD

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        View 22394 White Oak Road Leonardtown, MD MLS# MDSM2029800
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        $495,000
        4

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        3.0

        Baths

        2,507

        Sq.Ft.

        22394 White Oak Road

        Leonardtown, MD

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        View 41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722
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        1 of 63
        $620,000
        5

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        4.0

        Baths

        3,724

        Sq.Ft.

        41377 Doctors Crossing Road

        Leonardtown, MD

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        View 20798 Waterside Drive Leonardtown, MD MLS# MDSM2029666
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          1 of 33
          $450,000
          2

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          1.0

          Baths

          1,018

          Sq.Ft.

          20798 Waterside Drive

          Leonardtown, MD

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          View Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482
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          $479,900
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          Lot 113 - 23696 Weeping Willow Way

          Leonardtown, MD

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          View Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484
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          $489,900
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          Lot 133 - 23691 Weeping Willow Way

          Leonardtown, MD

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          View Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486
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          OPEN HOUSE: Thursday 4/30 11:00 AM - 4:00 PM
          $449,900
          4

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          3.1

          Baths

          Lot 101 - 23713 Dragonfly Lane

          Leonardtown, MD

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          View Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488
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          OPEN HOUSE: Thursday 4/30 11:00 AM - 4:00 PM
          $449,900
          4

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          3.1

          Baths

          Lot 99 - 23725 Dragonfly Lane

          Leonardtown, MD

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          View 41516 Marwood Circle Leonardtown, MD MLS# MDSM2029470
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            1 of 55
            $437,000
            3

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            3.1

            Baths

            2,402

            Sq.Ft.

            41516 Marwood Circle

            Leonardtown, MD

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            View 22175 Bayside Road Leonardtown, MD MLS# MDSM2029056
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              1 of 25
              $315,000
              2

              Beds

              2.0

              Baths

              1,192

              Sq.Ft.

              22175 Bayside Road

              Leonardtown, MD

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              View Lot 100 - 23719 Dragonfly Lane Leonardtown, MD MLS# MDSM2029208
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              1 of 45
              $449,900
              4

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              3.1

              Baths

              2,571

              Sq.Ft.

              Lot 100 - 23719 Dragonfly Lane

              Leonardtown, MD

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              View Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218
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              Save Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218
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              $489,900
              4

              Beds

              3.1

              Baths

              3,095

              Sq.Ft.

              Lot 117 - 23720 Weeping Willow Way

              Leonardtown, MD

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              View Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202
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              $479,900
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              Lot 102 - 23707 Dragonfly Lane

              Leonardtown, MD

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              View 22547 Landing Way Leonardtown, MD MLS# MDSM2029148
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                1 of 48
                $515,000
                3

                Beds

                3.1

                Baths

                2,764

                Sq.Ft.

                22547 Landing Way

                Leonardtown, MD

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                View St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070
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                  1 of 6
                  $175,000
                  Studio

                  Beds

                  0.0

                  Baths

                  St. Andrews Church Road

                  Leonardtown, MD

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                  View 20265 Hawks Way Leonardtown, MD MLS# MDSM2028774
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                    $149,900
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                    0.0

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                    20265 Hawks Way

                    Leonardtown, MD

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

                      Beds

                      0.0

                      Baths

                      1,691

                      Sq.Ft.

                      22615 Washington Street

                      Leonardtown, MD

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                      About Leonardtown

                      Listings in Leonardtown, MD

                      93

                      Estimated median home price

                      $550,000
                      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 - 100K2
                      $100K - 200K7
                      $200K - 300K2
                      $300K - 400K4
                      $400K - 500K28
                      $500K - 600K13
                      $600K - 700K17
                      $700K - 800K8
                      $800K - 900K4
                      $900K - 1M1
                      $1M - Max7

                      Homes for Sale by Type in Leonardtown, MD

                      Property TypeCount
                      Single Family57
                      Townhouse21
                      Condo1
                      Commercial1
                      Rental20
                      Lots and Land13
                      Condo/Town/CoOp0
                      CoOp0
                      Multi Family0
                      Mobile Home0
                      Farms0

                      (Data as of 4/30/2026)

                      Find Properties in Leonardtown, MD

                      Leonardtown, MD Information

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