6,736

Leonardtown, MD Homes

Section Image
  • 23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    23092 Town Run Dr, Leonardtown, MD 20650
    /76

    $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 $621,909

    Last Listing Agent Robin Errington CENTURY 21 New Millennium

    23092 Town Run Dr, Leonardtown, MD 20650
    • 21871 Fairway Dr, Leonardtown, MD 20650
      21871 Fairway Dr, Leonardtown, MD 20650
      21871 Fairway Dr, Leonardtown, MD 20650
      /44

      Est $654,519 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 3,332 Sq Ft

      21871 Fairway Dr, Leonardtown, MD 20650

      21871 Fairway Dr, Leonardtown, MD 20650
  • 42279 Bird Haven Dr, Leonardtown, MD 20650
    42279 Bird Haven Dr, Leonardtown, MD 20650
    42279 Bird Haven Dr, Leonardtown, MD 20650
    /65

    $600,000 Sold Jun 17, 2025

    42279 Bird Haven Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,139 Sq Ft
    • Built 2002

    Last Sold Summary

    • $191/SF
    • 4 Days On Market

    Current Estimated Value $602,018

    Last Listing Agent Mike Jordan CENTURY 21 New Millennium

    42279 Bird Haven Dr, Leonardtown, MD 20650
    • 39834 Big Pine Trail, Leonardtown, MD 20650
      39834 Big Pine Trail, Leonardtown, MD 20650
      39834 Big Pine Trail, Leonardtown, MD 20650
      /12

      Est $350,733 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      39834 Big Pine Trail, Leonardtown, MD 20650

      39834 Big Pine Trail, Leonardtown, MD 20650
  • 40095 Greentree Dr, Leonardtown, MD 20650
    40095 Greentree Dr, Leonardtown, MD 20650
    40095 Greentree Dr, Leonardtown, MD 20650
    /90

    $961,000 Sold Mar 14, 2025

    40095 Greentree Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,416 Sq Ft
    • Built 2022

    Last Sold Summary

    • $218/SF
    • 14 Days On Market

    Current Estimated Value $958,584

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    40095 Greentree Dr, Leonardtown, MD 20650
    • 22135 Cartwright Rd, Leonardtown, MD 20650
      22135 Cartwright Rd, Leonardtown, MD 20650
      22135 Cartwright Rd, Leonardtown, MD 20650
      /30

      Est $459,750 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,836 Sq Ft

      22135 Cartwright Rd, Leonardtown, MD 20650

      22135 Cartwright Rd, Leonardtown, MD 20650
  • 45474 Medleys Neck Rd, Leonardtown, MD 20650
    45474 Medleys Neck Rd, Leonardtown, MD 20650
    45474 Medleys Neck Rd, Leonardtown, MD 20650
    /88

    $635,000 Sold Dec 15, 2025

    45474 Medleys Neck Rd, Leonardtown, MD 20650

    • 3 Beds
    • 3 Baths
    • 2,653 Sq Ft
    • Built 1981

    Last Sold Summary

    • $239/SF
    • 31 Days On Market

    Last Listing Agent Erin Barber CENTURY 21 New Millennium

    45474 Medleys Neck Rd, Leonardtown, MD 20650
    • 21104 Rosebay Way, Leonardtown, MD 20650
      21104 Rosebay Way, Leonardtown, MD 20650
      21104 Rosebay Way, Leonardtown, MD 20650
      /99

      Est $634,168 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,680 Sq Ft

      21104 Rosebay Way, Leonardtown, MD 20650

      21104 Rosebay Way, Leonardtown, MD 20650
  • Lot 91- 23694 Dragonfly Ln, Leonardtown, MD 20650
    Lot 91- 23694 Dragonfly Ln, Leonardtown, MD 20650
    Lot 91- 23694 Dragonfly Ln, Leonardtown, MD 20650
    /40

    $439,900 Sold Dec 03, 2025

    Lot 91- 23694 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 34 Days On Market

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 91- 23694 Dragonfly Ln, Leonardtown, MD 20650
    • 18878 Hodges Ln, Leonardtown, MD 20650
      18878 Hodges Ln, Leonardtown, MD 20650
      18878 Hodges Ln, Leonardtown, MD 20650
      /91

      Est $1,126,625 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 4,184 Sq Ft

      18878 Hodges Ln, Leonardtown, MD 20650

      18878 Hodges Ln, Leonardtown, MD 20650
  • 40459 Breton View Dr, Leonardtown, MD 20650
    40459 Breton View Dr, Leonardtown, MD 20650
    40459 Breton View Dr, Leonardtown, MD 20650
    /47

    $375,000 Sold Jan 30, 2025

    40459 Breton View Dr, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,286 Sq Ft
    • Built 1989

    Last Sold Summary

    • $164/SF
    • 10 Days On Market

    Current Estimated Value $390,580

    Last Listing Agent Chris Norris JR. Topside Realty

    40459 Breton View Dr, Leonardtown, MD 20650
    • 21764 Potomac View Dr, Leonardtown, MD 20650
      21764 Potomac View Dr, Leonardtown, MD 20650
      21764 Potomac View Dr, Leonardtown, MD 20650
      /68

      Est $456,709 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,264 Sq Ft

      21764 Potomac View Dr, Leonardtown, MD 20650

      21764 Potomac View Dr, Leonardtown, MD 20650
  • 23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    23730 Hicks Dr, Leonardtown, MD 20650
    /25

    $402,000 Sold Oct 31, 2025

    23730 Hicks Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft
    • Built 1975

    Last Sold Summary

    • $202/SF
    • 49 Days On Market

    Last Listing Agent Kimberlee Randall Group EXP Realty, LLC

    23730 Hicks Dr, Leonardtown, MD 20650
    • 23255 Hollywood Rd, Leonardtown, MD 20650
      23255 Hollywood Rd, Leonardtown, MD 20650
      23255 Hollywood Rd, Leonardtown, MD 20650
      /42

      Est $343,005 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,584 Sq Ft

      23255 Hollywood Rd, Leonardtown, MD 20650

      23255 Hollywood Rd, Leonardtown, MD 20650
  • 40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee Ln, Leonardtown, MD 20650
    40801 Kiskadee Ln, Leonardtown, MD 20650
    /72

    $740,000 Sold Sep 18, 2025

    40801 Kiskadee Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3 Baths
    • 6,064 Sq Ft
    • Built 2002

    Last Sold Summary

    • $122/SF
    • 8 Days On Market

    Current Estimated Value $750,552

    Last Listing Agent Pattee McInerney Scott McInerney RE/MAX One

    40801 Kiskadee Ln, Leonardtown, MD 20650
    • 40883 Meadow Dr, Leonardtown, MD 20650
      40883 Meadow Dr, Leonardtown, MD 20650
      40883 Meadow Dr, Leonardtown, MD 20650
      /95

      Est $555,759 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,264 Sq Ft

      40883 Meadow Dr, Leonardtown, MD 20650

      40883 Meadow Dr, Leonardtown, MD 20650
  • 23641 Belmar Dr, Leonardtown, MD 20650
    23641 Belmar Dr, Leonardtown, MD 20650
    23641 Belmar Dr, Leonardtown, MD 20650
    /42

    $630,000 Sold Jul 10, 2025

    23641 Belmar Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,236 Sq Ft
    • Built 2012

    Last Sold Summary

    • $195/SF
    • 0 Days On Market

    Current Estimated Value $628,219

    Last Listing Agent Heather Foster RE/MAX One

    23641 Belmar Dr, Leonardtown, MD 20650
    • 43225 Prince Pine Ct, Leonardtown, MD 20650
      43225 Prince Pine Ct, Leonardtown, MD 20650
      43225 Prince Pine Ct, Leonardtown, MD 20650
      /74

      Est $626,980 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,960 Sq Ft

      43225 Prince Pine Ct, Leonardtown, MD 20650

      43225 Prince Pine Ct, Leonardtown, MD 20650
  • 22542 Landing Way, Leonardtown, MD 20650
    22542 Landing Way, Leonardtown, MD 20650
    22542 Landing Way, Leonardtown, MD 20650
    /42

    $517,000 Sold Aug 27, 2025

    22542 Landing Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,752 Sq Ft
    • Built 2005

    Last Sold Summary

    • $188/SF
    • 21 Days On Market

    Current Estimated Value $517,631

    Last Listing Agent Trish Brow EXP Realty, LLC

    22542 Landing Way, Leonardtown, MD 20650
    • 20990 Woodmere Dr, Leonardtown, MD 20650
      20990 Woodmere Dr, Leonardtown, MD 20650
      20990 Woodmere Dr, Leonardtown, MD 20650
      /40

      Est $523,566 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,404 Sq Ft

      20990 Woodmere Dr, Leonardtown, MD 20650

      20990 Woodmere Dr, Leonardtown, MD 20650
  • 22855 White Swan Way, Leonardtown, MD 20650
    22855 White Swan Way, Leonardtown, MD 20650
    22855 White Swan Way, Leonardtown, MD 20650
    /46

    $950,000 Sold Jun 02, 2025

    22855 White Swan Way, Leonardtown, MD 20650

    • 5 Beds
    • 5.5 Baths
    • 6,762 Sq Ft
    • Built 2001

    Last Sold Summary

    • $140/SF
    • 30 Days On Market

    Current Estimated Value $950,194

    Last Listing Agent Barbara Stellway KW Metro Center

    22855 White Swan Way, Leonardtown, MD 20650
    • 40812 Spring House Ln, Leonardtown, MD 20650
      40812 Spring House Ln, Leonardtown, MD 20650
      40812 Spring House Ln, Leonardtown, MD 20650
      /30

      Est $474,307 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,628 Sq Ft

      40812 Spring House Ln, Leonardtown, MD 20650

      40812 Spring House Ln, Leonardtown, MD 20650
  • 23265 Lindsay Dr, Leonardtown, MD 20650
    23265 Lindsay Dr, Leonardtown, MD 20650
    23265 Lindsay Dr, Leonardtown, MD 20650
    /59

    $435,000 Sold Aug 07, 2025

    23265 Lindsay Dr, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,306 Sq Ft
    • Built 2017

    Last Sold Summary

    • $189/SF
    • 3 Days On Market

    Current Estimated Value $435,007

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

    23265 Lindsay Dr, Leonardtown, MD 20650
    • 41910 Nazareth Ct, Leonardtown, MD 20650
      41910 Nazareth Ct, Leonardtown, MD 20650
      41910 Nazareth Ct, Leonardtown, MD 20650
      /41

      Est $493,277 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,861 Sq Ft

      41910 Nazareth Ct, Leonardtown, MD 20650

      41910 Nazareth Ct, Leonardtown, MD 20650
  • 40972 Mollies Way, Leonardtown, MD 20650
    40972 Mollies Way, Leonardtown, MD 20650
    40972 Mollies Way, Leonardtown, MD 20650
    /83

    $1,700,000 Sold Aug 21, 2025

    40972 Mollies Way, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 3,459 Sq Ft
    • Built 1995

    Last Sold Summary

    • $491/SF
    • 3 Days On Market

    Current Estimated Value $1,677,195

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    40972 Mollies Way, Leonardtown, MD 20650
    • 44661 Deerfield Rd, Leonardtown, MD 20650
      44661 Deerfield Rd, Leonardtown, MD 20650
      44661 Deerfield Rd, Leonardtown, MD 20650
      /54

      Est $488,162 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,016 Sq Ft

      44661 Deerfield Rd, Leonardtown, MD 20650

      44661 Deerfield Rd, Leonardtown, MD 20650
  • 41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    /53

    $680,000 Sold Oct 24, 2025

    41480 Whimsical Ct, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,825 Sq Ft
    • Built 2010

    Last Sold Summary

    • $178/SF
    • 32 Days On Market

    Last Listing Agent Fran Slade Compass

    41480 Whimsical Ct, Leonardtown, MD 20650
    • 41585 Yoke Ct, Leonardtown, MD 20650
      41585 Yoke Ct, Leonardtown, MD 20650
      41585 Yoke Ct, Leonardtown, MD 20650
      /62

      Est $669,187 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,717 Sq Ft

      41585 Yoke Ct, Leonardtown, MD 20650

      41585 Yoke Ct, Leonardtown, MD 20650
  • 22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    /65

    $614,900 Sold Dec 11, 2025

    22626 Chickadee Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,048 Sq Ft
    • Built 2002

    Last Sold Summary

    • $202/SF
    • 110 Days On Market

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    22626 Chickadee Ln, Leonardtown, MD 20650
    • 42291 Bird Haven Dr, Leonardtown, MD 20650
      42291 Bird Haven Dr, Leonardtown, MD 20650
      42291 Bird Haven Dr, Leonardtown, MD 20650
      /55

      Est $580,547 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,332 Sq Ft

      42291 Bird Haven Dr, Leonardtown, MD 20650

      42291 Bird Haven Dr, Leonardtown, MD 20650
  • 23647 Hansel Ct, Leonardtown, MD 20650
    23647 Hansel Ct, Leonardtown, MD 20650
    23647 Hansel Ct, Leonardtown, MD 20650
    /74

    $660,000 Sold Sep 29, 2025

    23647 Hansel Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,194 Sq Ft
    • Built 2010

    Last Sold Summary

    • $207/SF
    • 12 Days On Market

    Current Estimated Value $656,725

    Last Listing Agent Heather Foster RE/MAX One

    23647 Hansel Ct, Leonardtown, MD 20650
    • 43731 Stephenson Dr, Leonardtown, MD 20650
      43731 Stephenson Dr, Leonardtown, MD 20650
      43731 Stephenson Dr, Leonardtown, MD 20650
      /25

      Est $493,861 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,398 Sq Ft

      43731 Stephenson Dr, Leonardtown, MD 20650

      43731 Stephenson Dr, Leonardtown, MD 20650
  • 42297 Riverwinds Dr, Leonardtown, MD 20650
    42297 Riverwinds Dr, Leonardtown, MD 20650
    42297 Riverwinds Dr, Leonardtown, MD 20650
    /56

    $1,450,000 Sold Mar 26, 2025

    42297 Riverwinds Dr, Leonardtown, MD 20650

    • 4 Beds
    • 7 Baths
    • 3,709 Sq Ft
    • Built 1983

    Last Sold Summary

    • $391/SF
    • 4 Days On Market

    Current Estimated Value $1,474,447

    Last Listing Agent Carol Kalmus-Choporis CENTURY 21 New Millennium

    42297 Riverwinds Dr, Leonardtown, MD 20650
    • 20947 Chestnut Ridge Dr, Leonardtown, MD 20650
      20947 Chestnut Ridge Dr, Leonardtown, MD 20650
      20947 Chestnut Ridge Dr, Leonardtown, MD 20650
      /60

      Est $565,504 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,386 Sq Ft

      20947 Chestnut Ridge Dr, Leonardtown, MD 20650

      20947 Chestnut Ridge Dr, Leonardtown, MD 20650
  • 41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    /53

    $625,000 Sold Dec 10, 2025

    41402 Silver Charm Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,046 Sq Ft
    • Built 2010

    Last Sold Summary

    • $154/SF
    • 25 Days On Market

    Last Listing Agent Billy Rabbitt The Southside Group Real Estate

    41402 Silver Charm Ct, Leonardtown, MD 20650
    • 22264 Nomoni St, Leonardtown, MD 20650
      22264 Nomoni St, Leonardtown, MD 20650
      22264 Nomoni St, Leonardtown, MD 20650
      /22

      Est $268,598 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 864 Sq Ft

      22264 Nomoni St, Leonardtown, MD 20650

      22264 Nomoni St, Leonardtown, MD 20650
  • Lot 94- 23712 Dragonfly Ln, Leonardtown, MD 20650
    Lot 94- 23712 Dragonfly Ln, Leonardtown, MD 20650
    Lot 94- 23712 Dragonfly Ln, Leonardtown, MD 20650
    /51

    $469,900 Sold Nov 25, 2025

    Lot 94- 23712 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Bernth RE/MAX One

    Lot 94- 23712 Dragonfly Ln, Leonardtown, MD 20650
    • 41850 Tomey Ct, Leonardtown, MD 20650
      41850 Tomey Ct, Leonardtown, MD 20650
      41850 Tomey Ct, Leonardtown, MD 20650
      /31

      Est $447,359 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,760 Sq Ft

      41850 Tomey Ct, Leonardtown, MD 20650

      41850 Tomey Ct, Leonardtown, MD 20650
  • 23280 Hollywood Rd, Leonardtown, MD 20650
    23280 Hollywood Rd, Leonardtown, MD 20650
    23280 Hollywood Rd, Leonardtown, MD 20650
    /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 $334,170

    Last Listing Agent Carol Kalmus-Choporis CENTURY 21 New Millennium

    23280 Hollywood Rd, Leonardtown, MD 20650
    • 44143 Woodmont Dr, Leonardtown, MD 20650
      44143 Woodmont Dr, Leonardtown, MD 20650
      44143 Woodmont Dr, Leonardtown, MD 20650
      /65

      Est $633,546 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,748 Sq Ft

      44143 Woodmont Dr, Leonardtown, MD 20650

      44143 Woodmont Dr, Leonardtown, MD 20650

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Maryland St Marys County Leonardtown

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