219

Recently Sold Leonardtown, MD Homes

Section Image
  • /20

    $330,000

    Sold Sep 16, 2025

    23280 Hollywood Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,402 Sq Ft
    • Built 1956

    Last Sold Summary

    • $235/SF
    • 7 Days On Market

    Current Estimated Value $335,694

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    23280 Hollywood Rd, Leonardtown, MD 20650
  • /43

    $710,000

    Sold Sep 05, 2025

    20620 Laurel Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3 Baths
    • 3,500 Sq Ft
    • Built 2001

    Last Sold Summary

    • $203/SF
    • 4 Days On Market

    Current Estimated Value $708,287

    Last Listing Agent Amy Gallo RE/MAX One

    20620 Laurel Ct, Leonardtown, MD 20650
  • /34

    $615,000

    Sold Jun 27, 2025

    20540 Deer Wood Park Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,850 Sq Ft
    • Built 1995

    Last Sold Summary

    • $160/SF
    • 9 Days On Market

    Current Estimated Value $624,175

    Last Listing Agent Kelly Parks Coldwell Banker Realty

    20540 Deer Wood Park Dr, Leonardtown, MD 20650
  • /41

    $459,900

    Sold Feb 17, 2026

    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 37 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650
  • /57

    $560,000

    Sold Apr 24, 2026

    23299 Jenifer Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3 Baths
    • 3,482 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $161/SF
    • 10 Days On Market

    Current Estimated Value $553,775

    Last Listing Agent Conor Loughran CENTURY 21 New Millennium

    23299 Jenifer Ct, Leonardtown, MD 20650
  • /78

    $540,000

    Sold Jun 04, 2026

    40855 Spring House Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3 Baths
    • 3,464 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Below List Price
    • $156/SF
    • 22 Days On Market

    Current Estimated Value $564,778

    Last Listing Agent Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    40855 Spring House Ln, Leonardtown, MD 20650
  • /59

    $665,000

    Sold Nov 20, 2025

    41435 Osborne Ln, Leonardtown, MD 20650

    • 6 Beds
    • 4.5 Baths
    • 4,145 Sq Ft
    • Built 2018

    Last Sold Summary

    • $160/SF
    • 21 Days On Market

    Current Estimated Value $668,153

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    41435 Osborne Ln, Leonardtown, MD 20650
  • /50

    $406,000

    Sold Jul 25, 2025

    23745 Hicks Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 984 Sq Ft
    • Built 1978

    Last Sold Summary

    • $413/SF
    • 19 Days On Market

    Current Estimated Value $394,600

    Last Listing Agent Neil Smith Blackwell Real Estate, LLC

    23745 Hicks Dr, Leonardtown, MD 20650
  • /60

    $580,000

    Sold Jan 08, 2026

    21039 Woodmere Dr, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 4,112 Sq Ft
    • Built 1999

    Last Sold Summary

    • $141/SF
    • 48 Days On Market

    Current Estimated Value $597,180

    Last Listing Agent Wayne & Christine Floyd RE/MAX Realty Group

    21039 Woodmere Dr, Leonardtown, MD 20650
  • /68

    $578,000

    Sold Apr 14, 2026

    21117 Catnip Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,526 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $164/SF
    • 4 Days On Market

    Current Estimated Value $582,337

    Last Listing Agent Melissa Rodriguez RE/MAX One

    21117 Catnip Ct, Leonardtown, MD 20650
  • /25

    $302,000

    Sold May 12, 2026

    41810 Eastwick Ln Unit 2301, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,101 Sq Ft
    • Built 2009

    Last Sold Summary

    • 6% Above List Price
    • $274/SF
    • 1 Day On Market

    Current Estimated Value $287,111

    Last Listing Agent Patrick Dugan O'Brien Realty ERA Powered

    41810 Eastwick Ln Unit 2301, Leonardtown, MD 20650
  • /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 $505,219

    Last Listing Agent Kathryn Mausen Coldwell Banker Premier

    21056 Woodmere Dr, Leonardtown, MD 20650
  • /75

    $595,000

    Sold Jul 11, 2025

    23578 Pine Bluff Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 3,188 Sq Ft
    • Built 2011

    Last Sold Summary

    • $187/SF
    • 29 Days On Market

    Current Estimated Value $603,457

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    23578 Pine Bluff Way, Leonardtown, MD 20650
  • /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 Hefley RE/MAX One

    Lot 110 - 23678 Weeping Willow Way, Leonardtown, MD 20650
  • /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 $681,503

    Last Listing Agent Mary Helen Wiley Daly RE/MAX One

    39825 Sweetpea Ln, Leonardtown, MD 20650
  • /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 $476,349

    Last Listing Agent Sarah Reynolds Keller Williams Realty

    40910 Starling Ct, Leonardtown, MD 20650
  • /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 $516,314

    Last Listing Agent Katherine Dean RE/MAX One

    21920 Newtowne Neck Rd, Leonardtown, MD 20650
  • /72

    $449,900

    Sold Jul 31, 2025

    41554 Briarwood Cir, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,379 Sq Ft
    • Built 2022

    Last Sold Summary

    • $189/SF
    • 12 Days On Market

    Current Estimated Value $455,850

    Last Listing Agent Wayne & Christine Floyd RE/MAX Realty Group

    41554 Briarwood Cir, Leonardtown, MD 20650
  • /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 Hefley RE/MAX One

    Lot 112 - 23690 Weeping Willow Way, Leonardtown, MD 20650
  • /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 $648,452

    Last Listing Agent Heather Foster RE/MAX One

    23563 Belmar Dr, Leonardtown, MD 20650
  • /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 Hefley RE/MAX One

    Lot 95 - 23718 Dragonfly Ln, Leonardtown, MD 20650
  • /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 $671,719

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    23324 Lindsay Dr, Leonardtown, MD 20650
  • /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 $629,596

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    22305 Hanover Dr, Leonardtown, MD 20650
  • /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 $633,564

    Last Listing Agent Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
  • /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 $436,026

    Last Listing Agent Kelly Niland Home Towne Real Estate

    40295 Busy Corner Rd, Leonardtown, MD 20650
  • /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 $488,477

    Last Listing Agent Kelly Padgett Century 21 Redwood Realty

    21515 Our Drive Way, Leonardtown, MD 20650
  • /3

    $212,000

    Sold Aug 11, 2025

    20837 Camp Cosoma Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,016 Sq Ft
    • Built 1950

    Last Sold Summary

    • $209/SF
    • 3 Days On Market

    Current Estimated Value $225,580

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    20837 Camp Cosoma Rd, Leonardtown, MD 20650
  • /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 $458,780

    Last Listing Agent Jimmy Hayden RE/MAX One

    41923 Sara Ann Ct, Leonardtown, MD 20650
  • /41

    $479,900

    Sold Jul 31, 2025

    41997 Loker Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,330 Sq Ft
    • Built 2006

    Last Sold Summary

    • $206/SF
    • 5 Days On Market

    Current Estimated Value $482,286

    Last Listing Agent Jimmy Hayden RE/MAX One

    41997 Loker Ct, Leonardtown, MD 20650
  • /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 $582,717

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    43552 Bayberry Ct, Leonardtown, MD 20650
  • /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 $548,644

    Last Listing Agent Kelly Padgett Century 21 Redwood Realty

    22338 White Oak Rd, Leonardtown, MD 20650
  • /3

    $175,000

    Sold Dec 18, 2025

    40533 Breton Knolls Ct, Leonardtown, MD 20650

    • Land
    • 1.87 Acres
    • $93,583 per Acre

    Last Sold Summary

    • 1,153 Days On Market

    Current Estimated Value $362,558

    Last Listing Agent Mark Posey Greenmark Real Estate

    40533 Breton Knolls Ct, Leonardtown, MD 20650
  • /2

    $724,000

    Sold Apr 14, 2026

    44545 Brewer Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,243 Sq Ft
    • Built 2011

    Last Sold Summary

    • 7% Above List Price
    • $223/SF
    • 5 Days On Market

    Current Estimated Value $710,367

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    44545 Brewer Ln, Leonardtown, MD 20650
  • /2

    $635,000

    Sold May 28, 2026

    23590 Margrave Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft
    • Built 2014

    Last Sold Summary

    • $170/SF
    • 2 Days On Market

    Current Estimated Value $632,833

    Last Listing Agent Darrin Carter RE/MAX One

    23590 Margrave Dr, Leonardtown, MD 20650
  • /40

    $439,900

    Sold Dec 09, 2025

    Lot 92- 23700 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 29 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 92- 23700 Dragonfly Ln, Leonardtown, MD 20650
  • /50

    $681,000

    Sold Dec 10, 2025

    23098 Town Run Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,642 Sq Ft
    • Built 2022

    Last Sold Summary

    • $187/SF
    • 40 Days On Market

    Current Estimated Value $675,423

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    23098 Town Run Dr, Leonardtown, MD 20650
  • /34

    $449,900

    Sold May 26, 2026

    Lot 134 - 23685 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Last Sold Summary

    • $176/SF

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 134 - 23685 Weeping Willow Way, Leonardtown, MD 20650
  • /64

    $1,100,000

    Sold Jul 01, 2025

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650

    • 5 Beds
    • 5.5 Baths
    • 6,508 Sq Ft
    • Built 2009

    Last Sold Summary

    • $169/SF
    • 7 Days On Market

    Current Estimated Value $1,095,020

    Last Listing Agent Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
  • /25

    $400,000

    Sold Aug 15, 2025

    23888 Hollywood Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 1972

    Last Sold Summary

    • $276/SF
    • 3 Days On Market

    Current Estimated Value $414,361

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    23888 Hollywood Rd, Leonardtown, MD 20650
  • /13

    $100,000

    Sold May 08, 2026

    19921 Tower Hill Rd, Leonardtown, MD 20650

    • Land
    • 5.09 Acres
    • $19,646 per Acre

    Last Sold Summary

    • 71 Days On Market

    Last Listing Agent Jimmy Hayden RE/MAX One

    19921 Tower Hill Rd, Leonardtown, MD 20650

Showing Results 161 - 200, Page 5 of 6

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