6,740

Leonardtown, MD Homes

Section Image
    • 42297 Riverwinds Dr, Leonardtown, MD 20650
      42297 Riverwinds Dr, Leonardtown, MD 20650
      42297 Riverwinds Dr, Leonardtown, MD 20650
      /56

      Est $1,497,544

      Not Listed For Sale

      42297 Riverwinds Dr, Leonardtown, MD 20650

      • 4 Beds
      • 7 Baths
      • 3,709 Sq Ft
      • Built 1983
      42297 Riverwinds Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

  • 43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, 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 $634,208

    Last Listing Agent Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
    • 40880 Cooper Dr, Leonardtown, MD 20650
      40880 Cooper Dr, Leonardtown, MD 20650
      40880 Cooper Dr, Leonardtown, MD 20650
      /51

      Est $633,417

      Not Listed For Sale

      40880 Cooper Dr, Leonardtown, MD 20650

      • 4 Beds
      • 4 Baths
      • 3,156 Sq Ft
      • Built 1978
      40880 Cooper Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Leslie Suarez RLAH @properties

  • 40295 Busy Corner Rd, Leonardtown, MD 20650
    40295 Busy Corner Rd, Leonardtown, MD 20650
    40295 Busy Corner Rd, 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 $435,936

    Last Listing Agent Kelly Niland Home Towne Real Estate

    40295 Busy Corner Rd, Leonardtown, MD 20650
    • 40907 Cooper Dr, Leonardtown, MD 20650
      40907 Cooper Dr, Leonardtown, MD 20650
      40907 Cooper Dr, Leonardtown, MD 20650
      /56

      Est $460,527

      Not Listed For Sale

      40907 Cooper Dr, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 2,226 Sq Ft
      • Built 1984
      40907 Cooper Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Barbara Blades CENTURY 21 New Millennium

  • 21515 Our Drive Way, Leonardtown, MD 20650
    21515 Our Drive Way, Leonardtown, MD 20650
    21515 Our Drive Way, 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 $487,698

    Last Listing Agent Kelly Padgett Century 21 Redwood Realty

    21515 Our Drive Way, Leonardtown, MD 20650
    • 40481 Old Breton Beach Rd, Leonardtown, MD 20650
      40481 Old Breton Beach Rd, Leonardtown, MD 20650
      40481 Old Breton Beach Rd, Leonardtown, MD 20650
      /64

      Est $611,000

      Not Listed For Sale

      40481 Old Breton Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 2 Baths
      • 1,144 Sq Ft
      • Built 1961
      40481 Old Breton Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Dawn Riley Deep Roots Real Estate

  • 41923 Sara Ann Ct, Leonardtown, MD 20650
    41923 Sara Ann Ct, Leonardtown, MD 20650
    41923 Sara Ann Ct, 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 $454,350

    Last Listing Agent Jimmy Hayden RE/MAX One

    41923 Sara Ann Ct, Leonardtown, MD 20650
    • 21821 Cove Ln, Leonardtown, MD 20650
      21821 Cove Ln, Leonardtown, MD 20650
      21821 Cove Ln, Leonardtown, MD 20650
      /17

      Est $712,668

      Not Listed For Sale

      21821 Cove Ln, Leonardtown, MD 20650

      • 2 Beds
      • 3 Baths
      • 2,748 Sq Ft
      • Built 1967
      21821 Cove Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Barbara Stellway KW Metro Center

  • 43552 Bayberry Ct, Leonardtown, MD 20650
    43552 Bayberry 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 $584,383

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    43552 Bayberry Ct, Leonardtown, MD 20650
    • 40808 S 40 Dr, Leonardtown, MD 20650
      40808 S 40 Dr, Leonardtown, MD 20650
      40808 S 40 Dr, Leonardtown, MD 20650
      /24

      Est $449,101

      Not Listed For Sale

      40808 S 40 Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 2,242 Sq Ft
      • Built 1972
      40808 S 40 Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

  • 22394 White Oak Rd, Leonardtown, MD 20650
    22394 White Oak Rd, Leonardtown, MD 20650
    /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
    • 40778 S 40 Dr, Leonardtown, MD 20650
      40778 S 40 Dr, Leonardtown, MD 20650
      40778 S 40 Dr, Leonardtown, MD 20650
      /40

      Est $434,586

      Not Listed For Sale

      40778 S 40 Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1985
      40778 S 40 Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Tracey Summers CENTURY 21 New Millennium

  • 22338 White Oak Rd, Leonardtown, MD 20650
    22338 White Oak Rd, Leonardtown, MD 20650
    22338 White Oak Rd, 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 $550,141

    Last Listing Agent Kelly Padgett Century 21 Redwood Realty

    22338 White Oak Rd, Leonardtown, MD 20650
    • 21919 Budds Creek Rd, Leonardtown, MD 20650
      21919 Budds Creek Rd, Leonardtown, MD 20650
      21919 Budds Creek Rd, Leonardtown, MD 20650
      /48

      Est $375,271

      Not Listed For Sale

      21919 Budds Creek Rd, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 1,680 Sq Ft
      • Built 1957
      21919 Budds Creek Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Kimberly Scott RE/MAX Realty Group

  • 41482 Pensive St, Leonardtown, MD 20650
    41482 Pensive St, Leonardtown, MD 20650
    41482 Pensive St, Leonardtown, MD 20650
    /75

    $551,200

    Sold Jul 17, 2026

    41482 Pensive St, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,300 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Below List Price
    • $128/SF
    • 14 Days On Market

    Current Estimated Value $570,766

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    41482 Pensive St, Leonardtown, MD 20650
    • 23420 Hollywood Rd, Leonardtown, MD 20650
      23420 Hollywood Rd, Leonardtown, MD 20650
      23420 Hollywood Rd, Leonardtown, MD 20650
      /41

      Est $326,817

      Not Listed For Sale

      23420 Hollywood Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,466 Sq Ft
      • Built 1950
      23420 Hollywood Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Rita Jones The Southside Group Real Estate

  • 40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, Leonardtown, MD 20650
    40533 Breton Knolls Ct, 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 $354,146

    Last Listing Agent Mark Posey Greenmark Real Estate

    40533 Breton Knolls Ct, Leonardtown, MD 20650
    • 22380 White Oak Rd, Leonardtown, MD 20650
      22380 White Oak Rd, Leonardtown, MD 20650
      22380 White Oak Rd, Leonardtown, MD 20650
      /53

      Est $463,274

      Not Listed For Sale

      22380 White Oak Rd, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,680 Sq Ft
      • Built 1975
      22380 White Oak Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Diana Washabaugh CENTURY 21 New Millennium

  • 44545 Brewer Ln, Leonardtown, MD 20650
    44545 Brewer Ln, 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 $709,059

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    44545 Brewer Ln, Leonardtown, MD 20650
    • 20230 Big Oak Ln, Leonardtown, MD 20650
      20230 Big Oak Ln, Leonardtown, MD 20650
      20230 Big Oak Ln, Leonardtown, MD 20650
      /21

      Est $284,801

      Not Listed For Sale

      20230 Big Oak Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,588 Sq Ft
      • Built 1946
      20230 Big Oak Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Billy Rabbitt The Southside Group Real Estate

  • 23590 Margrave Dr, Leonardtown, MD 20650
    23590 Margrave Dr, 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 $634,828

    Last Listing Agent Darrin Carter RE/MAX One

    23590 Margrave Dr, Leonardtown, MD 20650
    • 40325 Rosebank Ln, Leonardtown, MD 20650
      40325 Rosebank Ln, Leonardtown, MD 20650
      40325 Rosebank Ln, Leonardtown, MD 20650
      /69

      Est $701,896

      Not Listed For Sale

      40325 Rosebank Ln, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,620 Sq Ft
      • Built 1966
      40325 Rosebank Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium

  • Lot 92- 23700 Dragonfly Ln, Leonardtown, MD 20650
    Lot 92- 23700 Dragonfly Ln, Leonardtown, MD 20650
    Lot 92- 23700 Dragonfly Ln, 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 Lee Hefley RE/MAX One

    Lot 92- 23700 Dragonfly Ln, Leonardtown, MD 20650
    • 41700 Mattingly St, Leonardtown, MD 20650
      41700 Mattingly St, Leonardtown, MD 20650
      41700 Mattingly St, Leonardtown, MD 20650
      /34

      Est $394,798

      Not Listed For Sale

      41700 Mattingly St, Leonardtown, MD 20650

      • 4 Beds
      • 2 Baths
      • 1,860 Sq Ft
      • Built 1952
      41700 Mattingly St, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Adam Chambers JPAR Real Estate Professionals

  • 23098 Town Run Dr, Leonardtown, MD 20650
    23098 Town Run Dr, Leonardtown, MD 20650
    23098 Town Run Dr, 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 $680,694

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    23098 Town Run Dr, Leonardtown, MD 20650
    • 21790 Cove Ln, Leonardtown, MD 20650
      21790 Cove Ln, Leonardtown, MD 20650
      21790 Cove Ln, Leonardtown, MD 20650
      /36

      Est $909,407

      Not Listed For Sale

      21790 Cove Ln, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,150 Sq Ft
      • Built 1961
      21790 Cove Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Mark Frisco CENTURY 21 New Millennium

  • Lot 134 - 23685 Weeping Willow Way, Leonardtown, MD 20650
    Lot 134 - 23685 Weeping Willow Way, Leonardtown, MD 20650
    Lot 134 - 23685 Weeping Willow Way, 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 Lee Hefley RE/MAX One

    Lot 134 - 23685 Weeping Willow Way, Leonardtown, MD 20650
    • 22331 Leonard St, Leonardtown, MD 20650
      22331 Leonard St, Leonardtown, MD 20650
      22331 Leonard St, Leonardtown, MD 20650
      /50

      Est $307,808

      Not Listed For Sale

      22331 Leonard St, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 1,152 Sq Ft
      • Built 1931
      22331 Leonard St, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Janet Weaver RE/MAX One

  • 23888 Hollywood Rd, Leonardtown, MD 20650
    23888 Hollywood Rd, Leonardtown, MD 20650
    23888 Hollywood Rd, 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 $399,087

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    23888 Hollywood Rd, Leonardtown, MD 20650
    • 23295 Maypole Rd, Leonardtown, MD 20650
      23295 Maypole Rd, Leonardtown, MD 20650
      23295 Maypole Rd, Leonardtown, MD 20650
      /56

      Est $422,728

      Not Listed For Sale

      23295 Maypole Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,947 Sq Ft
      • Built 1968
      23295 Maypole Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Jackie Randell CENTURY 21 New Millennium

  • 19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill Rd, Leonardtown, MD 20650
    19921 Tower Hill 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
    • 40688 S 40 Dr, Leonardtown, MD 20650
      40688 S 40 Dr, Leonardtown, MD 20650
      40688 S 40 Dr, Leonardtown, MD 20650
      /74

      Est $473,181

      Not Listed For Sale

      40688 S 40 Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,318 Sq Ft
      • Built 1978
      40688 S 40 Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Robin Errington CENTURY 21 New Millennium

  • 41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    /74

    $680,000

    Sold May 21, 2026

    41488 Pensive St, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,992 Sq Ft
    • Built 2008

    Last Sold Summary

    • $170/SF
    • 15 Days On Market

    Current Estimated Value $678,307

    Last Listing Agent Heather Foster RE/MAX One

    41488 Pensive St, Leonardtown, MD 20650
    • 20503 Deer Wood Park Dr, Leonardtown, MD 20650
      20503 Deer Wood Park Dr, Leonardtown, MD 20650
      20503 Deer Wood Park Dr, Leonardtown, MD 20650
      /117

      Est $761,300

      Not Listed For Sale

      20503 Deer Wood Park Dr, Leonardtown, MD 20650

      • 5 Beds
      • 5 Baths
      • 5,862 Sq Ft
      • Built 1997
      20503 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Tracey Summers CENTURY 21 New Millennium

  • 23220 Brandon Ct, Leonardtown, MD 20650
    23220 Brandon Ct, Leonardtown, MD 20650
    23220 Brandon Ct, Leonardtown, MD 20650
    /61

    $545,000

    Sold Sep 26, 2025

    23220 Brandon Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,102 Sq Ft
    • Built 2004

    Last Sold Summary

    • $259/SF
    • 3 Days On Market

    Current Estimated Value $542,254

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23220 Brandon Ct, Leonardtown, MD 20650
    • 20533 Deer Wood Park Dr, Leonardtown, MD 20650
      20533 Deer Wood Park Dr, Leonardtown, MD 20650
      20533 Deer Wood Park Dr, Leonardtown, MD 20650
      /87

      Est $741,284

      Not Listed For Sale

      20533 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 5,720 Sq Ft
      • Built 1997
      20533 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium

  • 22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, Leonardtown, MD 20650
    22798 Lawrence Ave, Leonardtown, MD 20650
    /46

    $350,000

    Sold Sep 19, 2025

    22798 Lawrence Ave, Leonardtown, MD 20650

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft
    • Built 1978

    Last Sold Summary

    • $302/SF
    • 28 Days On Market

    Current Estimated Value $348,744

    Last Listing Agent Barbara Click O'Brien Realty ERA Powered

    22798 Lawrence Ave, Leonardtown, MD 20650
    • 20418 Scarlet Tanager Way, Leonardtown, MD 20650
      20418 Scarlet Tanager Way, Leonardtown, MD 20650
      20418 Scarlet Tanager Way, Leonardtown, MD 20650
      /46

      Est $454,549

      Not Listed For Sale

      20418 Scarlet Tanager Way, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 2,116 Sq Ft
      • Built 1990
      20418 Scarlet Tanager Way, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Michele Hughes RE/MAX Realty Group

  • 23073 Town Run Dr, Leonardtown, MD 20650
    23073 Town Run Dr, Leonardtown, MD 20650
    23073 Town Run Dr, Leonardtown, MD 20650
    /47

    $646,000

    Sold May 28, 2026

    23073 Town Run Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,854 Sq Ft
    • Built 2022

    Last Sold Summary

    • 1% Above List Price
    • $226/SF
    • 2 Days On Market

    Current Estimated Value $641,383

    Last Listing Agent Laura Lee Hefley RE/MAX One

    23073 Town Run Dr, Leonardtown, MD 20650

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