6,740

Leonardtown, MD Homes

Section Image
    • /99

      Est $628,701

      Not Listed For Sale

      21104 Rosebay Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,680 Sq Ft
      • Built 2003
      21104 Rosebay Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Melissa Rodriguez RE/MAX One

  • /95

    $753,000

    Sold Jun 05, 2026

    21390 Little Saint Annes Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • Built 2003

    Last Sold Summary

    • 12% Above List Price
    • $215/SF
    • 2 Days On Market

    Current Estimated Value $743,137

    Last Listing Agent Jan Barnes CENTURY 21 New Millennium

    21390 Little Saint Annes Ln, Leonardtown, MD 20650
    • /25

      Est $447,469

      Not Listed For Sale

      21684 Potomac View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,504 Sq Ft
      • Built 2002
      21684 Potomac View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Terry Tenney Atlantic Southern Realty INC

  • /96

    $880,000

    Sold Jun 19, 2026

    21130 Someday Farm Ln, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 3,122 Sq Ft
    • Built 2011

    Last Sold Summary

    • 10% Above List Price
    • $282/SF
    • 6 Days On Market

    Current Estimated Value $863,637

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    21130 Someday Farm Ln, Leonardtown, MD 20650
    • /34

      Est $629,018

      Not Listed For Sale

      20540 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,850 Sq Ft
      • Built 1995
      20540 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kelly Parks Coldwell Banker Realty

  • /36

    $465,000

    Sold Nov 21, 2025

    44504 Watson Ln, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,304 Sq Ft
    • Built 2003

    Last Sold Summary

    • $202/SF
    • 17 Days On Market

    Current Estimated Value $470,605

    Last Listing Agent Danny Morris O'Brien Realty ERA Powered

    44504 Watson Ln, Leonardtown, MD 20650
    • /42

      Est $336,819

      Not Listed For Sale

      23255 Hollywood Rd, Leonardtown, MD 20650

      • 3 Beds
      • 1.5 Baths
      • 1,584 Sq Ft
      • Built 1930
      23255 Hollywood Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Kelly Padgett Century 21 Redwood Realty

  • /2

    $630,000

    Sold Aug 20, 2025

    41460 Challedon Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,252 Sq Ft
    • Built 2010

    Last Sold Summary

    • $194/SF
    • 2 Days On Market

    Current Estimated Value $636,968

    Last Listing Agent Heather Foster RE/MAX One

    41460 Challedon Way, Leonardtown, MD 20650
    • /95

      Est $564,549

      Not Listed For Sale

      40883 Meadow Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3 Baths
      • 2,264 Sq Ft
      • Built 1980
      40883 Meadow Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Ron Leonard Leonard Realty, Inc.

  • /18

    $175,000

    Sold Feb 02, 2026

    0 Kiskadee Ln, Leonardtown, MD 20650

    • Land
    • 3.53 Acres
    • $49,575 per Acre

    Last Sold Summary

    • 156 Days On Market

    Last Listing Agent Pattee McInerney Scott McInerney RE/MAX One

    0 Kiskadee Ln, Leonardtown, MD 20650
    • /74

      Est $624,077

      Not Listed For Sale

      43225 Prince Pine Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,960 Sq Ft
      • Built 1992
      43225 Prince Pine Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Natalya Ford RE/MAX One

  • /76

    $615,000

    Sold Jul 13, 2026

    21822 Riviera Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,384 Sq Ft
    • Built 1997

    Last Sold Summary

    • 3% Above List Price
    • $182/SF
    • 2 Days On Market

    Current Estimated Value $601,024

    Last Listing Agent Laura Lee Hefley RE/MAX One

    21822 Riviera Ct, Leonardtown, MD 20650
    • /109

      Est $676,572

      Not Listed For Sale

      40721 Merlin Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,469 Sq Ft
      • Built 2002
      40721 Merlin Way, Leonardtown, MD 20650

      Last Sold Summary

      • 110 Days On Market

      Last Listing Agent Ron Leonard Leonard Realty, Inc.

  • /32

    $425,000

    Sold Oct 22, 2025

    22362 Armstrong Dr, Leonardtown, MD 20650

    • 3 Beds
    • 3 Baths
    • 2,028 Sq Ft
    • Built 1973

    Last Sold Summary

    • 10% Below List Price
    • $210/SF
    • 207 Days On Market

    Current Estimated Value $420,539

    Last Listing Agent Chris Hill CENTURY 21 New Millennium

    22362 Armstrong Dr, Leonardtown, MD 20650
    • /40

      Est $523,889

      Not Listed For Sale

      20990 Woodmere Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,404 Sq Ft
      • Built 2001
      20990 Woodmere Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Amy Scott OE Realty

  • /27

    $335,000

    Sold Jul 07, 2026

    22381 Cedar St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft
    • Built 1961

    Last Sold Summary

    • 2% Above List Price
    • $260/SF
    • 16 Days On Market

    Current Estimated Value $324,811

    Last Listing Agent Deanna Rothstein RE/MAX One

    22381 Cedar St, Leonardtown, MD 20650
    • /71

      Est $602,334

      Not Listed For Sale

      42261 Bird Haven Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,233 Sq Ft
      • Built 2002
      42261 Bird Haven Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Melissa Rodriguez RE/MAX One

  • /50

    $520,000

    Sold Feb 17, 2026

    42043 Starlight Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft
    • Built 2004

    Last Sold Summary

    • $210/SF
    • 119 Days On Market

    Current Estimated Value $532,341

    Last Listing Agent Kimberly St. Laurent RE/MAX One

    42043 Starlight Dr, Leonardtown, MD 20650
    • /30

      Est $478,581

      Not Listed For Sale

      40812 Spring House Ln, Leonardtown, MD 20650

      • 5 Beds
      • 3 Baths
      • 3,628 Sq Ft
      • Built 1986
      40812 Spring House Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Helen Mattingly Wernecke Berkshire Hathaway HomeServices PenFed Realty

  • /52

    $540,000

    Sold Jul 16, 2026

    21737 Pinehurst Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 3,014 Sq Ft
    • Built 1990

    Last Sold Summary

    • $179/SF
    • 35 Days On Market

    Current Estimated Value $536,877

    Last Listing Agent Patrick Deighan CENTURY 21 New Millennium

    21737 Pinehurst Ct, Leonardtown, MD 20650
    • /54

      Est $477,867

      Not Listed For Sale

      44661 Deerfield Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 2,016 Sq Ft
      • Built 1991
      44661 Deerfield Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Theresa Shoptaw CENTURY 21 New Millennium

  • /40

    $497,400

    Sold May 12, 2026

    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 2% Above List Price

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650
    • /62

      Est $664,333

      Not Listed For Sale

      41585 Yoke Ct, Leonardtown, MD 20650

      • 4 Beds
      • 4.5 Baths
      • 3,717 Sq Ft
      • Built 1999
      41585 Yoke Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Jimmy Hayden RE/MAX One

  • /42

    $340,000

    Sold Jul 31, 2026

    22281 Nomoni St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1987

    Last Sold Summary

    • 6% Below List Price
    • $295/SF
    • 100 Days On Market

    Current Estimated Value $350,719

    Last Listing Agent Paul Fenton Coldwell Banker Premier

    22281 Nomoni St, Leonardtown, MD 20650
    • /22

      Est $269,603

      Not Listed For Sale

      22264 Nomoni St, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft
      • Built 1983
      22264 Nomoni St, Leonardtown, MD 20650

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Tammy Garner-Donegan Five Star Real Estate

  • /58

    $459,900

    Sold Nov 25, 2025

    Lot 97- 23730 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 18 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 97- 23730 Dragonfly Ln, Leonardtown, MD 20650
    • /44

      Est $605,097

      Not Listed For Sale

      20760 Chestnut Ridge Dr, Leonardtown, MD 20650

      • 6 Beds
      • 3.5 Baths
      • 3,492 Sq Ft
      • Built 1993
      20760 Chestnut Ridge Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Charlotte Long EXP Realty, LLC

  • /31

    $465,000

    Sold Feb 11, 2026

    21925 Budds Creek Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,527 Sq Ft
    • Built 1970

    Last Sold Summary

    • $184/SF
    • 72 Days On Market

    Current Estimated Value $463,552

    Last Listing Agent Jimmy Hayden RE/MAX One

    21925 Budds Creek Rd, Leonardtown, MD 20650
    • /112

      Est $718,725

      Not Listed For Sale

      40929 Falcon Way, Leonardtown, MD 20650

      • 3 Beds
      • 5 Baths
      • 3,712 Sq Ft
      • Built 1997
      40929 Falcon Way, Leonardtown, MD 20650

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

  • /55

    $328,000

    Sold Jul 23, 2026

    41704 Courthouse Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Above List Price
    • $171/SF
    • 1 Day On Market

    Current Estimated Value $309,979

    Last Listing Agent Heather Foster RE/MAX One

    41704 Courthouse Dr, Leonardtown, MD 20650
    • /56

      Est $477,244

      Not Listed For Sale

      22158 Monterey Place, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,782 Sq Ft
      • Built 1975
      22158 Monterey Place, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent C. Brandon Harrington PAX Real Estate

  • /41

    $599,900

    Sold Oct 30, 2025

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,061 Sq Ft
    • Built 1995

    Last Sold Summary

    • $196/SF
    • 94 Days On Market

    Current Estimated Value $622,913

    Last Listing Agent Lauren Garner EXP Realty, LLC

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    • /54

      Est $643,511

      Not Listed For Sale

      20640 Laurel Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,692 Sq Ft
      • Built 2001
      20640 Laurel Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

  • /2

    $750,000

    Sold May 28, 2026

    20752 Penansey Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 2,936 Sq Ft
    • Built 2010

    Last Sold Summary

    • $255/SF
    • 0 Days On Market

    Current Estimated Value $744,900

    Last Listing Agent Heather Foster RE/MAX One

    20752 Penansey Ln, Leonardtown, MD 20650
    • /8

      Est $257,139

      Not Listed For Sale

      42742 Moll Dyer Rd, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 736 Sq Ft
      • Built 1975
      42742 Moll Dyer Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 94 Days On Market

      Last Listing Agent Billy Rabbitt The Southside Group Real Estate

  • /72

    $537,500

    Sold Sep 30, 2025

    23674 Jm Gough Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,697 Sq Ft
    • Built 2005

    Last Sold Summary

    • $199/SF
    • 96 Days On Market

    Current Estimated Value $543,465

    Last Listing Agent Heather Foster RE/MAX One

    23674 Jm Gough Ct, Leonardtown, MD 20650
    • /6

      Est $324,198

      Not Listed For Sale

      44662 Blake Creek Rd, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 1,344 Sq Ft
      • Built 1963
      44662 Blake Creek Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Ruth Mudd RE/MAX One

  • 23092 Town Run Dr, Leonardtown, MD 20650

    $619,000

    Sold Oct 10, 2025

    23092 Town Run Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,806 Sq Ft
    • Built 2023

    Last Sold Summary

    • $163/SF
    • 32 Days On Market

    Current Estimated Value $646,912

    Last Listing Agent Robin Errington CENTURY 21 New Millennium

    23092 Town Run Dr, Leonardtown, MD 20650
    • /48

      Est $673,737

      Not Listed For Sale

      22835 Avenmar Dr, Leonardtown, MD 20650

      • 5 Beds
      • 2.5 Baths
      • 3,498 Sq Ft
      • Built 2001
      22835 Avenmar Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Rachel Hutton JPAR Real Estate Professionals

  • /40

    $457,400

    Sold Aug 03, 2026

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 2% Above List Price
    • 129 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

Showing Results 361 - 400, Page 10 of 18

How to Buy a Home How to Finance a Home How to Sell a Home