View 41600 Miss Bessie Drive Leonardtown, MD MLS# MDSM2031384
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$428,799
3

Beds

2.0

Baths

1,910

Sq.Ft.

41600 Miss Bessie Drive

Leonardtown, MD

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View 39944 Lady Baltimore Avenue Leonardtown, MD MLS# MDSM2031394
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$395,000
5

Beds

2.1

Baths

2,169

Sq.Ft.

39944 Lady Baltimore Avenue

Leonardtown, MD

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View Lot 156 - 23634 Dragonfly Lane Leonardtown, MD MLS# MDSM2031220
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Save Lot 156 - 23634 Dragonfly Lane Leonardtown, MD MLS# MDSM2031220
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$449,900
4

Beds

3.1

Baths

2,554

Sq.Ft.

Lot 156 - 23634 Dragonfly Lane

Leonardtown, MD

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The time to sell is now! THE TIME TO SELL IS NOW!
View 41395 Omaha Court Leonardtown, MD MLS# MDSM2031298
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$715,000
5

Beds

3.1

Baths

4,367

Sq.Ft.

41395 Omaha Court

Leonardtown, MD

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View 43430 Browns Lane Leonardtown, MD MLS# MDSM2031286
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$605,000
5

Beds

3.2

Baths

2,756

Sq.Ft.

43430 Browns Lane

Leonardtown, MD

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View 39645 Sweetpea Lane Leonardtown, MD MLS# MDSM2031258
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$799,900
Studio

Beds

0.0

Baths

39645 Sweetpea Lane

Leonardtown, MD

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View 23642 Hansel Court Leonardtown, MD MLS# MDSM2031224
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$649,900
4

Beds

3.1

Baths

3,726

Sq.Ft.

23642 Hansel Court

Leonardtown, MD

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View 21390 Little Saint Annes Lane Leonardtown, MD MLS# MDSM2031120
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    $739,500
    4

    Beds

    3.1

    Baths

    3,500

    Sq.Ft.

    21390 Little Saint Annes Lane

    Leonardtown, MD

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    View 21737 Pinehurst Court Leonardtown, MD MLS# MDSM2031122
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    $540,000
    3

    Beds

    2.0

    Baths

    3,014

    Sq.Ft.

    21737 Pinehurst Court

    Leonardtown, MD

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    View 22381 Cedar Street Leonardtown, MD MLS# MDSM2031080
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      $329,900
      3

      Beds

      2.0

      Baths

      1,287

      Sq.Ft.

      22381 Cedar Street

      Leonardtown, MD

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      View 21983 Point Lookout Road Leonardtown, MD MLS# MDSM2031060
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      $389,900
      3

      Beds

      2.0

      Baths

      1,144

      Sq.Ft.

      21983 Point Lookout Road

      Leonardtown, MD

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      View Lot 131 - 23703 Weeping Willow Way Way Leonardtown, MD MLS# MDSM2031070
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      Save Lot 131 - 23703 Weeping Willow Way Way Leonardtown, MD MLS# MDSM2031070
      1 of 34
      $449,900
      4

      Beds

      3.1

      Baths

      2,554

      Sq.Ft.

      Lot 131 - 23703 Weeping Willow Way Way

      Leonardtown, MD

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      View Lot 140 - 23659 Dragonfly Lane Leonardtown, MD MLS# MDSM2031072
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      1 of 45
      $449,900
      4

      Beds

      3.1

      Baths

      2,604

      Sq.Ft.

      Lot 140 - 23659 Dragonfly Lane

      Leonardtown, MD

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      View Lot 159 - 23652 Dragonfly Lane Leonardtown, MD MLS# MDSM2031076
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      Save Lot 159 - 23652 Dragonfly Lane Leonardtown, MD MLS# MDSM2031076
      1 of 30
      $479,900
      4

      Beds

      3.1

      Baths

      2,966

      Sq.Ft.

      Lot 159 - 23652 Dragonfly Lane

      Leonardtown, MD

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      View Lot 151 - 23790 Wisteria Lane Leonardtown, MD MLS# MDSM2031078
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      Save Lot 151 - 23790 Wisteria Lane Leonardtown, MD MLS# MDSM2031078
      1 of 46
      $489,900
      4

      Beds

      3.1

      Baths

      3,095

      Sq.Ft.

      Lot 151 - 23790 Wisteria Lane

      Leonardtown, MD

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      View 23008 Hopton Lane Leonardtown, MD MLS# MDSM2031024
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        1 of 43
        $559,900
        3

        Beds

        3.0

        Baths

        2,688

        Sq.Ft.

        23008 Hopton Lane

        Leonardtown, MD

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        View Lot 136 - 23673 Weeping Willow Way Leonardtown, MD MLS# MDSM2031006
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        1 of 48
        $449,900
        4

        Beds

        3.1

        Baths

        2,554

        Sq.Ft.

        Lot 136 - 23673 Weeping Willow Way

        Leonardtown, MD

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        View Lot 134 - 23685 Weeping Willow Way Leonardtown, MD MLS# MDSM2031008
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        Save Lot 134 - 23685 Weeping Willow Way Leonardtown, MD MLS# MDSM2031008
        1 of 34
        $449,900
        4

        Beds

        3.1

        Baths

        2,554

        Sq.Ft.

        Lot 134 - 23685 Weeping Willow Way

        Leonardtown, MD

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        View Lot 158 - 23646 Dragonfly Lane Leonardtown, MD MLS# MDSM2031014
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        Save Lot 158 - 23646 Dragonfly Lane Leonardtown, MD MLS# MDSM2031014
        1 of 34
        $449,900
        4

        Beds

        3.1

        Baths

        2,554

        Sq.Ft.

        Lot 158 - 23646 Dragonfly Lane

        Leonardtown, MD

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        View 22394 White Oak Road Leonardtown, MD MLS# MDSM2030988
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          1 of 32
          $485,000
          4

          Beds

          3.0

          Baths

          2,507

          Sq.Ft.

          22394 White Oak Road

          Leonardtown, MD

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          About Leonardtown

          Listings in Leonardtown, MD

          92

          Estimated median home price

          $489,900
          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 - 100K3
          $100K - 200K6
          $200K - 300K1
          $300K - 400K6
          $400K - 500K32
          $500K - 600K12
          $600K - 700K14
          $700K - 800K9
          $800K - 900K3
          $900K - 1M1
          $1M - Max5

          Homes for Sale by Type in Leonardtown, MD

          Property TypeCount
          Single Family53
          Townhouse24
          Condo0
          Commercial1
          Rental18
          Lots and Land14
          Condo/Town/CoOp0
          CoOp0
          Multi Family0
          Mobile Home0
          Farms0

          (Data as of 5/23/2026)

          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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