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

Bright
Courtesy of RE/MAX ONE
View 23207 Moakley Street Leonardtown, MD MLS# MDSM2030226
    Save 23207 Moakley Street Leonardtown, MD MLS# MDSM2030226
    1 of 60
    $520,000
    3

    Beds

    2.1

    Baths

    1,926

    Sq.Ft.

    23207 Moakley Street

    Leonardtown, MD

    Bright
    Courtesy of RE/MAX ONE
    View Lot 110 - 23678 Weeping Willow Way Leonardtown, MD MLS# MDSM2030030
    • New Construction
    Save Lot 110 - 23678 Weeping Willow Way Leonardtown, MD MLS# MDSM2030030
    1 of 45
    OPEN HOUSE: Thursday 4/23 11:00 AM - 4:00 PM
    $449,900
    4

    Beds

    3.1

    Baths

    2,571

    Sq.Ft.

    Lot 110 - 23678 Weeping Willow Way

    Leonardtown, MD

    Bright
    Courtesy of RE/MAX ONE
    The time to sell is now! THE TIME TO SELL IS NOW!
    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 45
    OPEN HOUSE: Thursday 4/23 11:00 AM - 3:45 PM
    $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 21767 Potomac View Drive Leonardtown, MD MLS# MDSM2030068
      Save 21767 Potomac View Drive Leonardtown, MD MLS# MDSM2030068
      1 of 81
      $555,000
      4

      Beds

      3.1

      Baths

      4,384

      Sq.Ft.

      21767 Potomac View Drive

      Leonardtown, MD

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      Courtesy of CENTURY 21 NEW MILLENNIUM
      View 23590 Margrave Drive Leonardtown, MD MLS# MDSM2030104
        Save 23590 Margrave Drive Leonardtown, MD MLS# MDSM2030104
        1 of 56
        $635,000
        4

        Beds

        3.1

        Baths

        3,736

        Sq.Ft.

        23590 Margrave Drive

        Leonardtown, MD

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        Courtesy of RE/MAX ONE
        View 43552 Bayberry Court Leonardtown, MD MLS# MDSM2029930
          Save 43552 Bayberry Court Leonardtown, MD MLS# MDSM2029930
          1 of 32
          $579,900
          4

          Beds

          2.1

          Baths

          3,428

          Sq.Ft.

          43552 Bayberry Court

          Leonardtown, MD

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          Courtesy of CENTURY 21 NEW MILLENNIUM
          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 23299 Jenifer Court Leonardtown, MD MLS# MDSM2029912
            Save 23299 Jenifer Court Leonardtown, MD MLS# MDSM2029912
            1 of 57
            $550,000
            5

            Beds

            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
              Save 44731 Blake Creek Road Leonardtown, MD MLS# MDSM2029840
              1 of 1
              $365,000
              3

              Beds

              2.0

              Baths

              1,644

              Sq.Ft.

              44731 Blake Creek Road

              Leonardtown, MD

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              Courtesy of EXP REALTY, LLC
              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

                Beds

                0.0

                Baths

                0 Saint Andrews Church Rd

                Leonardtown, MD

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                Courtesy of WHITETAIL PROPERTIES REAL ESTATE, LLC
                View 22394 White Oak Road Leonardtown, MD MLS# MDSM2029800
                • Virtual Tour
                Save 22394 White Oak Road Leonardtown, MD MLS# MDSM2029800
                1 of 32
                $495,000
                4

                Beds

                3.0

                Baths

                2,507

                Sq.Ft.

                22394 White Oak Road

                Leonardtown, MD

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                Courtesy of KW METRO CENTER
                View 41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722
                • Virtual Tour
                Save 41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722
                1 of 63
                $620,000
                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 41497 Affirmed Way Leonardtown, MD MLS# MDSM2029650
                  Save 41497 Affirmed Way Leonardtown, MD MLS# MDSM2029650
                  1 of 83
                  $655,000
                  5

                  Beds

                  3.1

                  Baths

                  3,934

                  Sq.Ft.

                  41497 Affirmed Way

                  Leonardtown, MD

                  Bright
                  Courtesy of RE/MAX ONE
                  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

                    Bright
                    Courtesy of RE/MAX ONE
                    View 22224 Monterey Place Leonardtown, MD MLS# MDSM2029434
                      Save 22224 Monterey Place Leonardtown, MD MLS# MDSM2029434
                      1 of 29
                      $459,900
                      4

                      Beds

                      3.0

                      Baths

                      2,176

                      Sq.Ft.

                      22224 Monterey Place

                      Leonardtown, MD

                      Bright
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                      View Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482
                      • New Construction with Virtual Tour
                      Save Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482
                      1 of 42
                      $479,900
                      4

                      Beds

                      3.1

                      Baths

                      Lot 113 - 23696 Weeping Willow Way

                      Leonardtown, MD

                      Bright
                      Courtesy of RE/MAX ONE
                      View Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484
                      • New Construction with Virtual Tour
                      Save Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484
                      1 of 40
                      $489,900
                      4

                      Beds

                      3.1

                      Baths

                      Lot 133 - 23691 Weeping Willow Way

                      Leonardtown, MD

                      Bright
                      Courtesy of RE/MAX ONE
                      View Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486
                      • New Construction with Virtual Tour
                      Save Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486
                      1 of 34
                      OPEN HOUSE: Thursday 4/23 11:00 AM - 4:00 PM
                      $449,900
                      4

                      Beds

                      3.1

                      Baths

                      Lot 101 - 23713 Dragonfly Lane

                      Leonardtown, MD

                      Bright
                      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 35
                      OPEN HOUSE: Thursday 4/23 11:00 AM - 4:00 PM
                      $449,900
                      4

                      Beds

                      3.1

                      Baths

                      Lot 99 - 23725 Dragonfly Lane

                      Leonardtown, MD

                      Bright
                      Courtesy of RE/MAX ONE

                      About Leonardtown

                      Listings in Leonardtown, MD

                      90

                      Estimated median home price

                      $535,000
                      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 - 300K1
                      $300K - 400K5
                      $400K - 500K28
                      $500K - 600K12
                      $600K - 700K15
                      $700K - 800K8
                      $800K - 900K4
                      $900K - 1M1
                      $1M - Max7

                      Homes for Sale by Type in Leonardtown, MD

                      Property TypeCount
                      Single Family55
                      Townhouse20
                      Condo1
                      Commercial1
                      Rental20
                      Lots and Land13
                      Condo/Town/CoOp0
                      CoOp0
                      Multi Family0
                      Mobile Home0
                      Farms0

                      (Data as of 4/23/2026)

                      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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