6,720

Leonardtown, MD Homes

Section Image
  • /56

    $500,000

    Sold Oct 23, 2025

    21056 Woodmere Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,205 Sq Ft
    • Built 1999

    Last Sold Summary

    • $227/SF
    • 108 Days On Market

    Current Estimated Value $505,725

    Last Listing Agent Kathryn Mausen Coldwell Banker Premier

    21056 Woodmere Dr, Leonardtown, MD 20650
    • /27

      Est $470,574

      Not Listed For Sale

      41952 Loker Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,084 Sq Ft
      • Built 2006
      41952 Loker Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Diane Fenwick RE/MAX One

  • /107

    $674,000

    Sold Sep 08, 2026

    20750 Deer Wood Park Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,381 Sq Ft
    • Built 1996

    Last Sold Summary

    • $199/SF
    • 4 Days On Market

    Current Estimated Value $631,720

    Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

    20750 Deer Wood Park Dr, Leonardtown, MD 20650
    • /42

      Est $793,194

      Not Listed For Sale

      41041 Knight Rd, Leonardtown, MD 20650

      • 6 Beds
      • 5 Baths
      • 5,716 Sq Ft
      • Built 2006
      41041 Knight Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Connie Gunn CENTURY 21 New Millennium

  • /45

    $449,900

    Sold May 27, 2026

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Last Sold Summary

    • $175/SF
    • 28 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
    • /22

      Est $314,111

      Not Listed For Sale

      20483 White Point Rd, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 1,160 Sq Ft
      • Built 1953
      20483 White Point Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Theresa Shoptaw CENTURY 21 New Millennium

  • /80

    $700,000

    Sold Mar 31, 2026

    39825 Sweetpea Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,442 Sq Ft
    • Built 1985

    Last Sold Summary

    • $287/SF
    • 121 Days On Market

    Current Estimated Value $699,670

    Last Listing Agent Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
    • /67

      Est $688,609

      Not Listed For Sale

      21620 Coves End Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,541 Sq Ft
      • Built 2001
      21620 Coves End Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Hannah Cole Real Broker, LLC

  • /37

    $70,000

    Sold Sep 04, 2026

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650

    • Land
    • 4.11 Acres
    • $17,032 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 71 Days On Market

    Last Listing Agent Casey Kennedy Whitetail Properties Real Estate, LLC

    0 0 Saint Andrews Church Rd, Leonardtown, MD 20650
    • /56

      Est $689,577

      Not Listed For Sale

      23960 R G Way, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,788 Sq Ft
      • Built 1993
      23960 R G Way, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Dorothy Bistransin Redfin Corp

  • /2

    $475,000

    Sold Mar 27, 2026

    40910 Starling Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 3,012 Sq Ft
    • Built 1978

    Last Sold Summary

    • $158/SF
    • 2 Days On Market

    Current Estimated Value $476,819

    Last Listing Agent Sarah Reynolds Keller Williams Realty

    40910 Starling Ct, Leonardtown, MD 20650
    • /49

      Est $769,812

      Not Listed For Sale

      22876 White Swan Way, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,984 Sq Ft
      • Built 2002
      22876 White Swan Way, Leonardtown, MD 20650

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Ross Simone RE/MAX One

  • /57

    $520,000

    Sold Jan 30, 2026

    21920 Newtowne Neck Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,291 Sq Ft
    • Built 2018

    Last Sold Summary

    • $227/SF
    • 65 Days On Market

    Current Estimated Value $517,141

    Last Listing Agent Katherine Dean RE/MAX One

    21920 Newtowne Neck Rd, Leonardtown, MD 20650
    • /46

      Est $971,691

      Not Listed For Sale

      22855 White Swan Way, Leonardtown, MD 20650

      • 5 Beds
      • 5.5 Baths
      • 6,762 Sq Ft
      • Built 2001
      22855 White Swan Way, Leonardtown, MD 20650

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Barbara Stellway KW Metro Center

  • /46

    $499,900

    Sold Apr 17, 2026

    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Last Sold Summary

    • 2% Above List Price
    • $162/SF
    • 12 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650
    • /83

      Est $1,697,983

      Not Listed For Sale

      40972 Mollies Way, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 3,459 Sq Ft
      • Built 1995
      40972 Mollies Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Mark Frisco CENTURY 21 New Millennium

  • /69

    $650,000

    Sold May 29, 2026

    23563 Belmar Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,299 Sq Ft
    • Built 2008

    Last Sold Summary

    • $197/SF
    • 42 Days On Market

    Current Estimated Value $648,963

    Last Listing Agent Heather Foster RE/MAX One

    23563 Belmar Dr, Leonardtown, MD 20650
    • /50

      Est $458,944

      Not Listed For Sale

      42601 Wilderness Rd, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,181 Sq Ft
      • Built 1997
      42601 Wilderness Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Connie Gunn CENTURY 21 New Millennium

  • /35

    $439,900

    Sold Jan 30, 2026

    Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 82 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650
    • /51

      Est $390,888

      Not Listed For Sale

      39880 Lady Baltimore Ave, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,348 Sq Ft
      • Built 1994
      39880 Lady Baltimore Ave, Leonardtown, MD 20650

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Matthew Burgan Infinitas Realty Group

  • /64

    $679,900

    Sold May 15, 2026

    23324 Lindsay Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,168 Sq Ft
    • Built 2022

    Last Sold Summary

    • 1% Above List Price
    • $163/SF
    • 2 Days On Market

    Current Estimated Value $679,543

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    23324 Lindsay Dr, Leonardtown, MD 20650
    • /70

      Est $657,857

      Not Listed For Sale

      21897 Fairway Dr, Leonardtown, MD 20650

      • 5 Beds
      • 2.5 Baths
      • 3,664 Sq Ft
      • Built 1997
      21897 Fairway Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Matthew Burgan Infinitas Realty Group

  • /57

    $629,000

    Sold Nov 18, 2025

    22305 Hanover Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,404 Sq Ft
    • Built 2005

    Last Sold Summary

    • $185/SF
    • 7 Days On Market

    Current Estimated Value $639,465

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    22305 Hanover Dr, Leonardtown, MD 20650
    • /47

      Est $399,346

      Not Listed For Sale

      40459 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,286 Sq Ft
      • Built 1989
      40459 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Chris Norris JR. Topside Realty

  • /61

    $635,000

    Sold Apr 15, 2026

    43018 Bluejay Ln, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft
    • Built 2019

    Last Sold Summary

    • $220/SF
    • 131 Days On Market

    Current Estimated Value $636,382

    Last Listing Agent Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
    • /105

      Est $889,786

      Not Listed For Sale

      21821 Rosebank Ct, Leonardtown, MD 20650

      • 5 Beds
      • 4 Baths
      • 4,200 Sq Ft
      • Built 1972
      21821 Rosebank Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

  • /34

    $439,900

    Sold Jun 18, 2026

    40295 Busy Corner Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 1,624 Sq Ft
    • Built 2002

    Last Sold Summary

    • $271/SF
    • 7 Days On Market

    Current Estimated Value $437,560

    Last Listing Agent Kelly Niland Home Towne Real Estate

    40295 Busy Corner Rd, Leonardtown, MD 20650
    • /56

      Est $892,830

      Not Listed For Sale

      21829 Rosebank Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,428 Sq Ft
      • Built 1979
      21829 Rosebank Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Janet Weaver RE/MAX One

  • /70

    $492,000

    Sold Nov 21, 2025

    21515 Our Drive Way, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1988

    Last Sold Summary

    • $266/SF
    • 2 Days On Market

    Current Estimated Value $487,698

    Last Listing Agent Kelly Padgett Century 21 Redwood Realty

    21515 Our Drive Way, Leonardtown, MD 20650
    • /61

      Est $1,036,995

      Not Listed For Sale

      41390 Philip Ln, Leonardtown, MD 20650

      • 6 Beds
      • 5 Baths
      • 5,846 Sq Ft
      • Built 1994
      41390 Philip Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Dorothy Bistransin Redfin Corp

  • /33

    $455,000

    Sold Jun 10, 2026

    41923 Sara Ann Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $224/SF
    • 14 Days On Market

    Current Estimated Value $454,350

    Last Listing Agent Jimmy Hayden RE/MAX One

    41923 Sara Ann Ct, Leonardtown, MD 20650
    • /42

      Est $395,697

      Not Listed For Sale

      42820 Lytle Ln, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1988
      42820 Lytle Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Wayne Floyd RE/MAX One

  • /2

    $579,900

    Sold May 11, 2026

    43552 Bayberry Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 3,428 Sq Ft
    • Built 1991

    Last Sold Summary

    • 3% Below List Price
    • $169/SF
    • 14 Days On Market

    Current Estimated Value $584,383

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    43552 Bayberry Ct, Leonardtown, MD 20650
    • /55

      Est $922,277

      Not Listed For Sale

      21940 Maranatha Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,814 Sq Ft
      • Built 1993
      21940 Maranatha Way, Leonardtown, MD 20650

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Adam Chambers JPAR Real Estate Professionals

  • /2

    $485,000

    Sold Jun 30, 2026

    22394 White Oak Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,507 Sq Ft
    • Built 1974

    Last Sold Summary

    • $193/SF
    • 23 Days On Market

    Current Estimated Value $479,527

    Last Listing Agent Barbara Stellway KW Metro Center

    22394 White Oak Rd, Leonardtown, MD 20650
    • /98

      Est $1,165,065

      Not Listed For Sale

      21545 Breton View Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 3,980 Sq Ft
      • Built 1985
      21545 Breton View Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /66

    $550,000

    Sold Feb 09, 2026

    22338 White Oak Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,328 Sq Ft
    • Built 1989

    Last Sold Summary

    • $236/SF
    • 169 Days On Market

    Current Estimated Value $550,141

    Last Listing Agent Kelly Padgett Century 21 Redwood Realty

    22338 White Oak Rd, Leonardtown, MD 20650
    • /50

      Est $491,190

      Not Listed For Sale

      41740 Eldon Ct, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 2,791 Sq Ft
      • Built 1988
      41740 Eldon Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Tracey Summers CENTURY 21 New Millennium

  • /43

    $457,400

    Sold Aug 20, 2026

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Last Sold Summary

    • 2% Above List Price
    • $176/SF
    • 94 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
    • /79

      Est $659,618

      Not Listed For Sale

      22325 White Oak Rd, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,975 Sq Ft
      • Built 1999
      22325 White Oak Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Sharon Cox Century 21 Redwood Realty

Showing Results 441 - 480, Page 12 of 18

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