219

Recently Sold Leonardtown, MD Homes

Section Image
  • /45

    $449,900

    Sold Jun 25, 2026

    Lot 115 - 23708 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 115 - 23708 Weeping Willow Way, Leonardtown, MD 20650
  • /82

    $675,000

    Sold Aug 14, 2025

    44074 Medleys Neck Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,830 Sq Ft
    • Built 2006

    Last Sold Summary

    • $176/SF
    • 3 Days On Market

    Current Estimated Value $684,799

    Last Listing Agent Cynthia Ballard Century 21 Redwood Realty

    44074 Medleys Neck Rd, Leonardtown, MD 20650
  • /2

    $800,000

    Sold May 05, 2026

    40737 Bobwhite Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 5,454 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $147/SF
    • 23 Days On Market

    Current Estimated Value $810,873

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    40737 Bobwhite Ln, Leonardtown, MD 20650
  • /34

    $625,000

    Sold Sep 30, 2025

    23246 Lindsay Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,876 Sq Ft
    • Built 2017

    Last Sold Summary

    • $161/SF
    • 55 Days On Market

    Current Estimated Value $645,991

    Last Listing Agent Wanda White CENTURY 21 New Millennium

    23246 Lindsay Dr, Leonardtown, MD 20650
  • /43

    $459,900

    Sold Dec 02, 2025

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft
    • Built 2025

    Last Sold Summary

    • $155/SF
    • 29 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 93- 23706 Dragonfly Ln, Leonardtown, MD 20650
  • 22323 Saint Clements Ave, Leonardtown, MD 20650

    $300,000

    Sold Oct 15, 2025

    22323 Saint Clements Ave, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1955

    Last Sold Summary

    • $250/SF
    • 0 Days On Market

    Current Estimated Value $289,644

    Last Listing Agent Matthew Burgan Infinitas Realty Group

    22323 Saint Clements Ave, Leonardtown, MD 20650
  • /2

    $300,000

    Sold Jun 05, 2026

    40743 Magee Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,474 Sq Ft
    • Built 1975

    Last Sold Summary

    • $121/SF

    Current Estimated Value $483,715

    Last Listing Agent Chris Hill CENTURY 21 New Millennium

    40743 Magee Dr, Leonardtown, MD 20650
  • /48

    $360,000

    Sold Sep 26, 2025

    40480 Parsons Mill Rd, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,884 Sq Ft
    • Built 1974

    Last Sold Summary

    • $191/SF
    • 35 Days On Market

    Current Estimated Value $370,210

    Last Listing Agent John Gatton CENTURY 21 New Millennium

    40480 Parsons Mill Rd, Leonardtown, MD 20650
  • /79

    $639,000

    Sold Feb 02, 2026

    41430 Challedon Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • $142/SF
    • 12 Days On Market

    Current Estimated Value $645,261

    Last Listing Agent Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
  • /45

    $340,000

    Sold Apr 15, 2026

    23311 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $322/SF
    • 2 Days On Market

    Current Estimated Value $339,884

    Last Listing Agent JW Abney RE/MAX One

    23311 Point Lookout Rd, Leonardtown, MD 20650
  • /77

    $728,000

    Sold May 22, 2026

    41389 Holiday Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,385 Sq Ft
    • Built 2012

    Last Sold Summary

    • 2% Above List Price
    • $166/SF
    • 0 Days On Market

    Current Estimated Value $713,168

    Last Listing Agent Laura Hefley RE/MAX One

    41389 Holiday Ct, Leonardtown, MD 20650
  • /29

    $440,000

    Sold Apr 24, 2026

    22224 Monterey Place, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,176 Sq Ft
    • Built 1976

    Last Sold Summary

    • 6% Below List Price
    • $202/SF
    • 9 Days On Market

    Current Estimated Value $446,734

    Last Listing Agent Carol Kalmus-Choporis Century 21 Redwood Realty

    22224 Monterey Place, Leonardtown, MD 20650
  • /2

    $971,725

    Sold Sep 24, 2025

    40552 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 4.5 Baths
    • 4,000 Sq Ft
    • Built 2025

    Last Sold Summary

    • $243/SF
    • 764 Days On Market

    Current Estimated Value $761,000

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40552 Breton Knolls Ct, Leonardtown, MD 20650
  • /30

    $645,000

    Sold Oct 15, 2025

    41430 Whimsical Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,907 Sq Ft
    • Built 2011

    Last Sold Summary

    • $165/SF
    • 26 Days On Market

    Current Estimated Value $655,210

    Last Listing Agent Kristen Quinn Realty Navigator

    41430 Whimsical Ct, Leonardtown, MD 20650
  • /54

    $531,000

    Sold Jul 18, 2025

    41699 Courthouse Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3 Baths
    • 2,420 Sq Ft
    • Built 2012

    Last Sold Summary

    • $219/SF
    • 5 Days On Market

    Current Estimated Value $533,686

    Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

    41699 Courthouse Dr, Leonardtown, MD 20650
  • /48

    $515,000

    Sold Apr 29, 2026

    22547 Landing Way, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,764 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Below List Price
    • $186/SF
    • 57 Days On Market

    Current Estimated Value $517,411

    Last Listing Agent Trish Brow O'Brien Realty ERA Powered

    22547 Landing Way, Leonardtown, MD 20650
  • /15

    $485,000

    Sold Nov 14, 2025

    41130 Cryer Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1955

    Last Sold Summary

    • $326/SF
    • 115 Days On Market

    Current Estimated Value $505,520

    Last Listing Agent Sharon Cox CENTURY 21 New Millennium

    41130 Cryer Ct, Leonardtown, MD 20650
  • /2

    $435,000

    Sold Apr 20, 2026

    23369 Marview Ct, Leonardtown, MD 20650

    • 3 Beds
    • 3.5 Baths
    • 2,308 Sq Ft
    • Built 2017

    Last Sold Summary

    • $188/SF
    • 38 Days On Market

    Current Estimated Value $426,300

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23369 Marview Ct, Leonardtown, MD 20650
  • /45

    $510,000

    Sold Dec 17, 2025

    41467 Osborne Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,827 Sq Ft
    • Built 2018

    Last Sold Summary

    • $180/SF
    • 13 Days On Market

    Current Estimated Value $514,244

    Last Listing Agent Susan Vogel Turtle Town Real Estate, LLC.

    41467 Osborne Ln, Leonardtown, MD 20650
  • /42

    $483,400

    Sold Jun 05, 2026

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Last Sold Summary

    • 1% Above List Price
    • $163/SF

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 137- 23667 Weeping Willow Way, Leonardtown, MD 20650
  • /88

    $1,049,900

    Sold May 19, 2026

    40840 Greenwood Ln, Leonardtown, MD 20650

    • 9 Beds
    • 5 Baths
    • 6,476 Sq Ft
    • Built 2012

    Last Sold Summary

    • $162/SF
    • 6 Days On Market

    Current Estimated Value $1,040,230

    Last Listing Agent Romy Singh Samson Properties

    40840 Greenwood Ln, Leonardtown, MD 20650
  • /85

    $695,000

    Sold Jul 02, 2025

    23055 Town Run Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 4,019 Sq Ft
    • Built 2021

    Last Sold Summary

    • $173/SF
    • 0 Days On Market

    Current Estimated Value $698,935

    Last Listing Agent Laura Hefley RE/MAX One

    23055 Town Run Dr, Leonardtown, MD 20650
  • /32

    $465,000

    Sold Jan 23, 2026

    43543 Bayberry Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft
    • Built 1991

    Last Sold Summary

    • $268/SF
    • 7 Days On Market

    Current Estimated Value $459,980

    Last Listing Agent Colin McHugh O'Brien Realty ERA Powered

    43543 Bayberry Ct, Leonardtown, MD 20650
  • /45

    $639,000

    Sold Nov 17, 2025

    23534 Belmar Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,738 Sq Ft
    • Built 2008

    Last Sold Summary

    • $135/SF
    • 96 Days On Market

    Current Estimated Value $654,636

    Last Listing Agent Bill Oosterink CENTURY 21 New Millennium

    23534 Belmar Dr, Leonardtown, MD 20650
  • /78

    $709,000

    Sold Sep 24, 2025

    21385 Fairwood Ct, Leonardtown, MD 20650

    • 4 Beds
    • 4 Baths
    • 3,970 Sq Ft
    • Built 2011

    Last Sold Summary

    • $179/SF
    • 24 Days On Market

    Current Estimated Value $710,839

    Last Listing Agent Dawn Bell RE/MAX One

    21385 Fairwood Ct, Leonardtown, MD 20650
  • /63

    $665,000

    Sold Jun 15, 2026

    23592 Belmar Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 3,728 Sq Ft
    • Built 2009

    Last Sold Summary

    • 2% Below List Price
    • $178/SF
    • 20 Days On Market

    Current Estimated Value $679,948

    Last Listing Agent Heather Foster RE/MAX One

    23592 Belmar Dr, Leonardtown, MD 20650
  • /140

    $750,000

    Sold Aug 15, 2025

    41115 Paw Hollow Ln, Leonardtown, MD 20650

    • 4 Beds
    • 5.5 Baths
    • 6,116 Sq Ft
    • Built 1997

    Last Sold Summary

    • $123/SF
    • 49 Days On Market

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    41115 Paw Hollow Ln, Leonardtown, MD 20650
  • /71

    $1,215,200

    Sold Sep 08, 2025

    21055 Breton Beach Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 3,052 Sq Ft
    • Built 2006

    Last Sold Summary

    • $398/SF
    • 5 Days On Market

    Current Estimated Value $1,200,473

    Last Listing Agent Robert Gauger EXP Realty, LLC

    21055 Breton Beach Ct, Leonardtown, MD 20650
  • /40

    $469,900

    Sold Jan 27, 2026

    Lot 103 - 23701 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 73 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 103 - 23701 Dragonfly Ln, Leonardtown, MD 20650
  • /33

    $700,000

    Sold Apr 02, 2026

    21345 Fairwood Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,080 Sq Ft
    • Built 2012

    Last Sold Summary

    • $172/SF
    • 58 Days On Market

    Current Estimated Value $698,319

    Last Listing Agent Deanna Rothstein RE/MAX One

    21345 Fairwood Ct, Leonardtown, MD 20650
  • /15

    $475,000

    Sold Nov 14, 2025

    41650 Matthew Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,230 Sq Ft
    • Built 2006

    Last Sold Summary

    • $213/SF
    • 47 Days On Market

    Current Estimated Value $479,720

    Last Listing Agent Paula Turner Pax River Realty LLC

    41650 Matthew Ct, Leonardtown, MD 20650
  • /2

    $315,000

    Sold Apr 10, 2026

    22204 Nomoni St, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1930

    Last Sold Summary

    • $312/SF
    • 11 Days On Market

    Current Estimated Value $310,797

    Last Listing Agent Tig Wright Redfin Corp

    22204 Nomoni St, Leonardtown, MD 20650
  • /36

    $415,000

    Sold Oct 24, 2025

    23745 Bayside Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1975

    Last Sold Summary

    • $309/SF
    • 4 Days On Market

    Current Estimated Value $404,970

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    23745 Bayside Rd, Leonardtown, MD 20650
  • /2

    $365,000

    Sold Apr 30, 2026

    44731 Blake Creek Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,644 Sq Ft
    • Built 1976

    Last Sold Summary

    • $222/SF
    • 0 Days On Market

    Current Estimated Value $370,050

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    44731 Blake Creek Rd, Leonardtown, MD 20650
  • /43

    $445,000

    Sold Jul 08, 2025

    40905 Knight Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,820 Sq Ft
    • Built 1980

    Last Sold Summary

    • $245/SF
    • 82 Days On Market

    Current Estimated Value $447,333

    Last Listing Agent Rob Schou EXP Realty, LLC

    40905 Knight Rd, Leonardtown, MD 20650
  • /45

    $560,000

    Sold Mar 05, 2026

    20753 Chestnut Ridge Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,594 Sq Ft
    • Built 1994

    Last Sold Summary

    • 3% Below List Price
    • $216/SF
    • 56 Days On Market

    Current Estimated Value $561,971

    Last Listing Agent Tracey Summers CENTURY 21 New Millennium

    20753 Chestnut Ridge Dr, Leonardtown, MD 20650
  • /89

    $686,000

    Sold Oct 02, 2025

    23080 Town Run Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,794 Sq Ft
    • Built 2023

    Last Sold Summary

    • $181/SF
    • 36 Days On Market

    Current Estimated Value $693,036

    Last Listing Agent Laura Hefley RE/MAX One

    23080 Town Run Dr, Leonardtown, MD 20650
  • /2

    $287,000

    Sold Sep 15, 2025

    21784 Potomac View Dr, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1962

    Last Sold Summary

    • $272/SF
    • 4 Days On Market

    Current Estimated Value $292,266

    Last Listing Agent Mike Benton Home Towne Real Estate

    21784 Potomac View Dr, Leonardtown, MD 20650
  • /2

    $366,000

    Sold Jul 02, 2025

    24554 Pin Cushion Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft
    • Built 1965

    Last Sold Summary

    • $197/SF
    • 2 Days On Market

    Current Estimated Value $370,180

    Last Listing Agent Connie Fitzgerald RE/MAX One

    24554 Pin Cushion Rd, Leonardtown, MD 20650
  • /26

    $584,000

    Sold Sep 12, 2025

    23330 Lindsay Dr, Leonardtown, MD 20650

    • 3 Beds
    • 3 Baths
    • 1,926 Sq Ft
    • Built 2022

    Last Sold Summary

    • $303/SF
    • 0 Days On Market

    Current Estimated Value $570,695

    Last Listing Agent Kristen Quinn Realty Navigator

    23330 Lindsay Dr, Leonardtown, MD 20650

Showing Results 81 - 120, Page 3 of 6

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