View 21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756
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$299,000
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21365 Bogies Lane

Leonardtown, MD

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Courtesy of CENTURY 21 REDWOOD REALTY
View 41650 Miss Bessie Drive Leonardtown, MD MLS# MDSM2032186
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$155,000
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41650 Miss Bessie Drive

Leonardtown, MD

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Courtesy of CENTURY 21 NEW MILLENNIUM
View 43954 Main Way Road Leonardtown, MD MLS# MDSM2032426
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$469,900
3

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3.0

Baths

1,691

Sq.Ft.

43954 Main Way Road

Leonardtown, MD

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The time to sell is now! THE TIME TO SELL IS NOW!
View 40743 Magee Drive Leonardtown, MD MLS# MDSM2032410
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$359,777
4

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2.0

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2,474

Sq.Ft.

40743 Magee Drive

Leonardtown, MD

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Courtesy of REAL OF PENNSYLVANIA
View 40582 Port Place Leonardtown, MD MLS# MDSM2032246
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    1 of 46
    $439,900
    3

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    2.0

    Baths

    2,196

    Sq.Ft.

    40582 Port Place

    Leonardtown, MD

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    Courtesy of CENTURY 21 REDWOOD REALTY
    View 22332 Cedar Street Leonardtown, MD MLS# MDSM2032152
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      $329,900
      2

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      1.0

      Baths

      1,000

      Sq.Ft.

      22332 Cedar Street

      Leonardtown, MD

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      Courtesy of CENTURY 21 REDWOOD REALTY
      View 18800 Mckays Beach Road Leonardtown, MD MLS# MDSM2032014
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        1 of 16
        $465,000
        3

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        2.0

        Baths

        1,667

        Sq.Ft.

        18800 Mckays Beach Road

        Leonardtown, MD

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        Courtesy of RE/MAX ONE
        View Parcel 323 Tract 2 Washington Street Leonardtown, MD MLS# MDSM2032220
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          $399,000
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          Parcel 323 Tract 2 Washington Street

          Leonardtown, MD

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          Courtesy of EXP REALTY, LLC
          View 40659 Klear Court Leonardtown, MD MLS# MDSM2032108
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            $485,000
            4

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            2.1

            Baths

            2,774

            Sq.Ft.

            40659 Klear Court

            Leonardtown, MD

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            Courtesy of BALDUS REAL ESTATE, INC.
            View Whirlwind Road Leonardtown, MD MLS# MDSM2032048
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              1 of 17
              $288,900
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              0.0

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              Whirlwind Road

              Leonardtown, MD

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              Courtesy of RE/MAX ONE
              View Lot 114 - 23702 Weeping Willow Way Leonardtown, MD MLS# MDSM2031212
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              1 of 44
              $449,900
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              3.1

              Baths

              2,554

              Sq.Ft.

              Lot 114 - 23702 Weeping Willow Way

              Leonardtown, MD

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              View Lot 116 - 23714 Weeping Willow Way Leonardtown, MD MLS# MDSM2031214
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              OPEN HOUSE: Thursday 7/30 11:00 AM - 4:00 PM
              $449,900
              4

              Beds

              3.1

              Baths

              2,554

              Sq.Ft.

              Lot 116 - 23714 Weeping Willow Way

              Leonardtown, MD

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              View 23898 Speith Road Leonardtown, MD MLS# MDSM2031902
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                1 of 37
                $429,000
                3

                Beds

                2.0

                Baths

                1,632

                Sq.Ft.

                23898 Speith Road

                Leonardtown, MD

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                View 0 Saint Andrews Church Rd Leonardtown, MD MLS# MDSM2031794
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                  1 of 37
                  $93,500
                  Studio

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                  0.0

                  Baths

                  0 Saint Andrews Church Rd

                  Leonardtown, MD

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                  Courtesy of WHITETAIL PROPERTIES REAL ESTATE, LLC
                  View 42700 Moll Dyer Road Leonardtown, MD MLS# MDSM2031772
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                    $300,000
                    Studio

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                    0.0

                    Baths

                    42700 Moll Dyer Road

                    Leonardtown, MD

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                    Courtesy of COLDWELL BANKER PREMIER
                    View Lot 157 - 23640 Dragonfly Lane Leonardtown, MD MLS# MDSM2031226
                    • New Construction with Virtual Tour
                    Save Lot 157 - 23640 Dragonfly Lane Leonardtown, MD MLS# MDSM2031226
                    1 of 45
                    $454,900
                    4

                    Beds

                    3.1

                    Baths

                    2,571

                    Sq.Ft.

                    Lot 157 - 23640 Dragonfly Lane

                    Leonardtown, MD

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                    Courtesy of RE/MAX ONE
                    View Lot 130 - 23709 Weeping Willow Way Leonardtown, MD MLS# MDSM2031222
                    • New Construction with Virtual Tour
                    Save Lot 130 - 23709 Weeping Willow Way Leonardtown, MD MLS# MDSM2031222
                    1 of 16
                    $449,900
                    4

                    Beds

                    3.1

                    Baths

                    2,571

                    Sq.Ft.

                    Lot 130 - 23709 Weeping Willow Way

                    Leonardtown, MD

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                    View Lot 129 - 23715 Weeping Willow Way Leonardtown, MD MLS# MDSM2031218
                    • New Construction with Virtual Tour
                    Save Lot 129 - 23715 Weeping Willow Way Leonardtown, MD MLS# MDSM2031218
                    1 of 18
                    $449,900
                    4

                    Beds

                    3.1

                    Baths

                    2,554

                    Sq.Ft.

                    Lot 129 - 23715 Weeping Willow Way

                    Leonardtown, MD

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                    Courtesy of RE/MAX ONE
                    View Lot 154 - 23808 Wisteria Lane Leonardtown, MD MLS# MDSM2031458
                    • New Construction
                    Save Lot 154 - 23808 Wisteria Lane Leonardtown, MD MLS# MDSM2031458
                    1 of 16
                    $479,900
                    4

                    Beds

                    3.1

                    Baths

                    2,966

                    Sq.Ft.

                    Lot 154 - 23808 Wisteria Lane

                    Leonardtown, MD

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                    Courtesy of RE/MAX ONE
                    View Lot 156 - 23634 Dragonfly Lane Leonardtown, MD MLS# MDSM2031220
                    • New Construction with Virtual Tour
                    Save Lot 156 - 23634 Dragonfly Lane Leonardtown, MD MLS# MDSM2031220
                    1 of 7
                    $454,900
                    4

                    Beds

                    3.1

                    Baths

                    2,554

                    Sq.Ft.

                    Lot 156 - 23634 Dragonfly Lane

                    Leonardtown, MD

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                    Courtesy of RE/MAX ONE

                    About Leonardtown

                    Listings in Leonardtown, MD

                    79

                    Estimated median home price

                    $487,400
                    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 - 200K4
                    $200K - 300K4
                    $300K - 400K6
                    $400K - 500K28
                    $500K - 600K5
                    $600K - 700K13
                    $700K - 800K7
                    $800K - 900K2
                    $900K - 1M0
                    $1M - Max8

                    Homes for Sale by Type in Leonardtown, MD

                    Property TypeCount
                    Single Family42
                    Townhouse22
                    Condo0
                    Commercial0
                    Rental26
                    Lots and Land15
                    Condo/Town/CoOp0
                    CoOp0
                    Multi Family0
                    Mobile Home0
                    Farms0

                    (Data as of 7/28/2026)

                    Find Properties in Leonardtown, MD

                    Leonardtown, MD Information

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