View 39862 Big Pine Trl Leonardtown, MD MLS# MDSM2034592
    Save 39862 Big Pine Trl Leonardtown, MD MLS# MDSM2034592
    1 of 2
    $420,000
    4

    Beds

    2.1

    Baths

    1,656

    Sq.Ft.

    39862 Big Pine Trl

    Leonardtown, MD

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    Courtesy of THE SOUTHSIDE GROUP REAL ESTATE
    View 23305 Joanne Drive Leonardtown, MD MLS# MDSM2034440
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    1 of 42
    $550,000
    4

    Beds

    3.1

    Baths

    3,348

    Sq.Ft.

    23305 Joanne Drive

    Leonardtown, MD

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    View 40751 Merlin Way Leonardtown, MD MLS# MDSM2034420
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    $495,000
    5

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    2.1

    Baths

    2,601

    Sq.Ft.

    40751 Merlin Way

    Leonardtown, MD

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    The time to sell is now! THE TIME TO SELL IS NOW!
    View 22630 Quiet Lane Leonardtown, MD MLS# MDSM2034126
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      1 of 75
      $467,000
      3

      Beds

      2.1

      Baths

      1,568

      Sq.Ft.

      22630 Quiet Lane

      Leonardtown, MD

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      Courtesy of RE/MAX REALTY GROUP
      View 22301 White Oak Road Leonardtown, MD MLS# MDSM2034276
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      1 of 32
      $489,900
      3

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      2.1

      Baths

      1,976

      Sq.Ft.

      22301 White Oak Road

      Leonardtown, MD

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      View Lot 155 - 23628 Dragonfly Lane Leonardtown, MD MLS# MDSM2034206
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      OPEN HOUSE: Friday 11/13 3:00 PM - 3:15 PM
      $495,900
      1

      Beds

      3.1

      Baths

      3,095

      Sq.Ft.

      Lot 155 - 23628 Dragonfly Lane

      Leonardtown, MD

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      View Lot 145 - 23629 Dragonfly Lane Leonardtown, MD MLS# MDSM2034234
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      1 of 30
      $479,900
      4

      Beds

      3.1

      Baths

      2,966

      Sq.Ft.

      Lot 145 - 23629 Dragonfly Lane

      Leonardtown, MD

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      View 41608 Briarwood Circle Leonardtown, MD MLS# MDSM2034160
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        OPEN HOUSE: Saturday 11/14 11:00 AM - 3:00 PM
        $430,000
        3

        Beds

        3.1

        Baths

        2,379

        Sq.Ft.

        41608 Briarwood Circle

        Leonardtown, MD

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        View 23405 Marview Court Leonardtown, MD MLS# MDSM2034018
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        1 of 48
        $450,000
        3

        Beds

        3.1

        Baths

        2,306

        Sq.Ft.

        23405 Marview Court

        Leonardtown, MD

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        View 22538 Landing Way Leonardtown, MD MLS# MDSM2034058
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          1 of 52
          $505,000
          4

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          3.1

          Baths

          2,764

          Sq.Ft.

          22538 Landing Way

          Leonardtown, MD

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          View 43705 Redmond Road Leonardtown, MD MLS# MDSM2033914
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            1 of 22
            $450,000
            3

            Beds

            2.0

            Baths

            1,462

            Sq.Ft.

            43705 Redmond Road

            Leonardtown, MD

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            View 41495 Garrett Court Leonardtown, MD MLS# MDSM2033936
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              1 of 66
              $469,900
              3

              Beds

              2.0

              Baths

              1,710

              Sq.Ft.

              41495 Garrett Court

              Leonardtown, MD

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              View 43261 Cedarwood Court Leonardtown, MD MLS# MDSM2033908
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                1 of 22
                $475,000
                4

                Beds

                2.1

                Baths

                2,200

                Sq.Ft.

                43261 Cedarwood Court

                Leonardtown, MD

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                View 23208 Clarks Rest Road Leonardtown, MD MLS# MDSM2033840
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                  1 of 31
                  $539,000
                  4

                  Beds

                  3.1

                  Baths

                  3,006

                  Sq.Ft.

                  23208 Clarks Rest Road

                  Leonardtown, MD

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                  View 20410 Chingville Road Leonardtown, MD MLS# MDSM2033190
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                    1 of 29
                    $450,000
                    4

                    Beds

                    3.0

                    Baths

                    2,604

                    Sq.Ft.

                    20410 Chingville Road

                    Leonardtown, MD

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                    View 40659 Klear Court Leonardtown, MD MLS# MDSM2033354
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                      1 of 54
                      $429,000
                      4

                      Beds

                      2.1

                      Baths

                      2,774

                      Sq.Ft.

                      40659 Klear Court

                      Leonardtown, MD

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                      View Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226
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                      Save Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226
                      1 of 44
                      OPEN HOUSE: Friday 11/13 11:00 AM - 4:00 PM
                      $454,900
                      4

                      Beds

                      3.1

                      Baths

                      Lot 143 - 23641 Dragonfly Lane

                      Leonardtown, MD

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                      View 41888 Jenkins Court Leonardtown, MD MLS# MDSM2033062
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                        1 of 53
                        OPEN HOUSE: Sunday 11/15 1:00 PM - 3:00 PM
                        $500,000
                        4

                        Beds

                        3.1

                        Baths

                        2,562

                        Sq.Ft.

                        41888 Jenkins Court

                        Leonardtown, MD

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                        View 22010 Society Hill Road Leonardtown, MD MLS# MDSM2032698
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                        1 of 45
                        $560,000
                        4

                        Beds

                        3.0

                        Baths

                        2,730

                        Sq.Ft.

                        22010 Society Hill Road

                        Leonardtown, MD

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                        View 43954 Main Way Road Leonardtown, MD MLS# MDSM2032426
                          Save 43954 Main Way Road Leonardtown, MD MLS# MDSM2032426
                          1 of 28
                          $449,900
                          3

                          Beds

                          3.0

                          Baths

                          1,691

                          Sq.Ft.

                          43954 Main Way Road

                          Leonardtown, MD

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                          About Leonardtown

                          Listings in Leonardtown, MD

                          86

                          Estimated median home price

                          $517,450
                          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 - 100K1
                          $100K - 200K5
                          $200K - 300K6
                          $300K - 400K4
                          $400K - 500K26
                          $500K - 600K16
                          $600K - 700K13
                          $700K - 800K5
                          $800K - 900K1
                          $900K - 1M1
                          $1M - Max8

                          Homes for Sale by Type in Leonardtown, MD

                          Property TypeCount
                          Single Family59
                          Townhouse14
                          Condo0
                          Commercial0
                          Rental12
                          Lots and Land13
                          Condo/Town/CoOp0
                          CoOp0
                          Multi Family0
                          Mobile Home0
                          Farms0

                          (Data as of 11/13/2026)

                          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.

                          Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

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