6,772

Leonardtown, MD Homes

Section Image
  • /35

    $449,900

    Sold Apr 16, 2026

    Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 109 - 23672 Weeping Willow Way, Leonardtown, MD 20650
    • /37

      Est $637,547

      Not Listed For Sale

      41625 Ferber Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 4,524 Sq Ft
      • Built 2005
      41625 Ferber Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /35

    $840,000

    • Land
    • 10.2 Acres
    • $82,353 per Acre

    0 Ferny Hills Ln, Leonardtown, MD 20650

    Discover the ultimate canvas for your vision at this 10.2-acre waterfront parcel overlooking Breton Bay. This rare offering combines natural beauty, privacy, and opportunity—an ideal setting to create your own waterfront retreat.With perc approval already in place, the property is ready for your dream home. The land features a mix of open fields and wooded areas, with views of the bay and

    Jennifer Goddard CENTURY 21 New Millennium

    0 Ferny Hills Ln, Leonardtown, MD 20650
  • /86

    $595,000

    Sold Apr 14, 2026

    21749 Pinehurst Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,410 Sq Ft
    • Built 1993

    Last Sold Summary

    • 4% Above List Price
    • $174/SF
    • 2 Days On Market

    Current Estimated Value $589,826

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    21749 Pinehurst Ct, Leonardtown, MD 20650
    • /67

      Est $599,773

      Not Listed For Sale

      23626 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,916 Sq Ft
      • Built 2005
      23626 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 59 Days On Market

  • /82

    $675,000

    Sold Aug 14, 2025

    44074 Medleys Neck Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,830 Sq Ft
    • Built 2006

    Last Sold Summary

    • $176/SF
    • 3 Days On Market

    Current Estimated Value $684,799

    Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

    44074 Medleys Neck Rd, Leonardtown, MD 20650
    • /88

      Est $608,962

      Not Listed For Sale

      23689 Jm Gough Ct, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,828 Sq Ft
      • Built 2005
      23689 Jm Gough Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /41

    $572,000

    Sold Jun 09, 2025

    23635 Abraham Dr, Leonardtown, MD 20650

    • 6 Beds
    • 4 Baths
    • 3,272 Sq Ft
    • Built 2004

    Last Sold Summary

    • $175/SF
    • 2 Days On Market

    Current Estimated Value $576,477

    Last Listing Agent Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

    23635 Abraham Dr, Leonardtown, MD 20650
    • /43

      Est $578,711

      Not Listed For Sale

      21081 Rosebay St, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft
      • Built 2002
      21081 Rosebay St, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • /2

    $800,000

    Sold May 05, 2026

    40737 Bobwhite Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 5,454 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $147/SF
    • 23 Days On Market

    Current Estimated Value $810,873

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    40737 Bobwhite Ln, Leonardtown, MD 20650
    • /82

      Est $595,545

      Not Listed For Sale

      22030 Cartwright Rd, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 2,475 Sq Ft
      • Built 2005
      22030 Cartwright Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 24 Days On Market

  • /34

    $625,000

    Sold Sep 30, 2025

    23246 Lindsay Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,876 Sq Ft
    • Built 2017

    Last Sold Summary

    • $161/SF
    • 55 Days On Market

    Current Estimated Value $645,991

    Last Listing Agent Wanda White CENTURY 21 New Millennium

    23246 Lindsay Dr, Leonardtown, MD 20650
    • /30

      Est $334,572

      Not Listed For Sale

      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 1,344 Sq Ft
      • Built 1991
      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 61 Days On Market

  • /43

    $459,900

    Sold Dec 02, 2025

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft
    • Built 2025

    Last Sold Summary

    • $155/SF
    • 29 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
    • /42

      Est $657,653

      Not Listed For Sale

      20708 Waterside Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft
      • Built 1925
      20708 Waterside Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • 22323 Saint Clements Ave, Leonardtown, MD 20650

    $300,000

    Sold Oct 15, 2025

    22323 Saint Clements Ave, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1955

    Last Sold Summary

    • $250/SF
    • 0 Days On Market

    Current Estimated Value $289,644

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    22323 Saint Clements Ave, Leonardtown, MD 20650
    • /57

      Est $539,175

      Not Listed For Sale

      41898 Jenkins Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,689 Sq Ft
      • Built 2005
      41898 Jenkins Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /48

    $360,000

    Sold Sep 26, 2025

    40480 Parsons Mill Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,884 Sq Ft
    • Built 1974

    Last Sold Summary

    • $191/SF
    • 35 Days On Market

    Current Estimated Value $370,210

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    40480 Parsons Mill Rd, Leonardtown, MD 20650
    • /40

      Est $641,070

      Not Listed For Sale

      23258 Jenifer Ct, Leonardtown, MD 20650

      • 4 Beds
      • 5 Baths
      • 5,100 Sq Ft
      • Built 2005
      23258 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • /79

    $639,000

    Sold Feb 02, 2026

    41430 Challedon Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • $142/SF
    • 12 Days On Market

    Current Estimated Value $645,261

    Last Listing Agent Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
    • /18

      Est $404,180

      Not Listed For Sale

      40443 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,604 Sq Ft
      • Built 1994
      40443 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 36 Days On Market

  • /45

    $340,000

    Sold Apr 15, 2026

    23311 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $322/SF
    • 2 Days On Market

    Current Estimated Value $339,884

    Last Listing Agent JW Abney RE/MAX One

    23311 Point Lookout Rd, Leonardtown, MD 20650
    • /55

      Est $568,156

      Not Listed For Sale

      41935 Green Hills Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1998
      41935 Green Hills Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /77

    $728,000

    Sold May 22, 2026

    41389 Holiday Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,385 Sq Ft
    • Built 2012

    Last Sold Summary

    • 2% Above List Price
    • $166/SF
    • 0 Days On Market

    Current Estimated Value $713,168

    Last Listing Agent Laura Hefley RE/MAX One

    41389 Holiday Ct, Leonardtown, MD 20650
    • /41

      Est $444,372

      Not Listed For Sale

      21717 Meadow Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,488 Sq Ft
      • Built 1981
      21717 Meadow Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

  • /29

    $440,000

    Sold Apr 24, 2026

    22224 Monterey Place, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,176 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $202/SF
    • 9 Days On Market

    Current Estimated Value $446,734

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    22224 Monterey Place, Leonardtown, MD 20650
    • /72

      Est $577,465

      Not Listed For Sale

      23638 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 3,352 Sq Ft
      • Built 2005
      23638 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /2

    $971,725

    Sold Sep 24, 2025

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft
    • Built 2025

    Last Sold Summary

    • $243/SF
    • 764 Days On Market

    Current Estimated Value $761,000

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
    • /37

      Est $396,664

      Not Listed For Sale

      39862 Big Pine Trail, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 1,656 Sq Ft
      • Built 2002
      39862 Big Pine Trail, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /30

    $645,000

    Sold Oct 15, 2025

    41430 Whimsical Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft
    • Built 2011

    Last Sold Summary

    • $165/SF
    • 26 Days On Market

    Current Estimated Value $655,210

    Last Listing Agent Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
    • /37

      Est $498,593

      Not Listed For Sale

      41805 Meynard Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,715 Sq Ft
      • Built 2005
      41805 Meynard Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 47 Days On Market

  • /54

    $531,000

    Sold Jul 18, 2025

    41699 Courthouse Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3 Baths
    • 2,420 Sq Ft
    • Built 2012

    Last Sold Summary

    • $219/SF
    • 5 Days On Market

    Current Estimated Value $533,686

    Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

    41699 Courthouse Dr, Leonardtown, MD 20650
    • /28

      Est $408,054

      Not Listed For Sale

      39919 Lake Cecil Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,008 Sq Ft
      • Built 2004
      39919 Lake Cecil Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • /48

    $515,000

    Sold Apr 29, 2026

    22547 Landing Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $186/SF
    • 57 Days On Market

    Current Estimated Value $517,411

    Last Listing Agent Trish Brow O'Brien Realty ERA Powered

    22547 Landing Way, Leonardtown, MD 20650
    • /55

      Est $398,841

      Not Listed For Sale

      40905 Spring House Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1962
      40905 Spring House Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /15

    $485,000

    Sold Nov 14, 2025

    41130 Cryer Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1955

    Last Sold Summary

    • $326/SF
    • 115 Days On Market

    Current Estimated Value $505,520

    Last Listing Agent Sharon Cox CENTURY 21 New Millennium

    41130 Cryer Ct, Leonardtown, MD 20650
    • /80

      Est $654,168

      Not Listed For Sale

      23259 Jenifer Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,078 Sq Ft
      • Built 2005
      23259 Jenifer Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • /2

    $435,000

    Sold Apr 20, 2026

    23369 Marview Ct, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,308 Sq Ft
    • Built 2017

    Last Sold Summary

    • $188/SF
    • 38 Days On Market

    Current Estimated Value $426,300

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23369 Marview Ct, Leonardtown, MD 20650
    • /51

      Est $623,780

      Not Listed For Sale

      22202 Hanover Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 3,261 Sq Ft
      • Built 2005
      22202 Hanover Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • /45

    $510,000

    Sold Dec 17, 2025

    41467 Osborne Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,827 Sq Ft
    • Built 2018

    Last Sold Summary

    • $180/SF
    • 13 Days On Market

    Current Estimated Value $514,244

    Last Listing Agent Susan Vogel Turtle Town Real Estate, LLC.

    41467 Osborne Ln, Leonardtown, MD 20650

Showing Results 241 - 280, Page 7 of 18

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