218

Recently Sold Leonardtown, MD Homes

Section Image
  • /83

    $655,000

    Sold Apr 24, 2026

    41497 Affirmed Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,934 Sq Ft
    • Built 2008

    Last Sold Summary

    • $166/SF
    • 2 Days On Market

    Current Estimated Value $653,952

    Last Listing Agent Heather Foster RE/MAX One

    41497 Affirmed Way, Leonardtown, MD 20650
  • /86

    $633,000

    Sold Sep 19, 2025

    22272 Orchard Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,745 Sq Ft
    • Built 2004

    Last Sold Summary

    • $169/SF
    • 1 Day On Market

    Current Estimated Value $646,198

    Last Listing Agent Christina Reed RE/MAX One

    22272 Orchard Ct, Leonardtown, MD 20650
  • /2

    $1,100,000

    Sold May 15, 2026

    20045 Tower Hill Rd, Leonardtown, MD 20650

    • 5 Beds
    • 7 Baths
    • 7,376 Sq Ft
    • Built 1973

    Last Sold Summary

    • 24% Below List Price
    • $149/SF
    • 12 Days On Market

    Current Estimated Value $1,141,458

    Last Listing Agent Barbara Stellway KW Metro Center

    20045 Tower Hill Rd, Leonardtown, MD 20650
  • /21

    $731,084

    Sold Dec 04, 2025

    40744 Fawns Rest Way, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 3,313 Sq Ft
    • Built 2025

    Last Sold Summary

    • $221/SF
    • 0 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    40744 Fawns Rest Way, Leonardtown, MD 20650
  • /56

    $961,000

    Sold May 28, 2026

    40003 Tippit Rd, Leonardtown, MD 20650

    • 3 Beds
    • 3 Baths
    • 2,490 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $386/SF
    • 23 Days On Market

    Current Estimated Value $930,561

    Last Listing Agent Charlotte Long EXP Realty, LLC

    40003 Tippit Rd, Leonardtown, MD 20650
  • /32

    $518,500

    Sold Dec 05, 2025

    22539 Landing Way, Leonardtown, MD 20650

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

    Last Sold Summary

    • $188/SF
    • 12 Days On Market

    Current Estimated Value $517,622

    Last Listing Agent Trish Brow O'Brien Realty ERA Powered

    22539 Landing Way, Leonardtown, MD 20650
  • /79

    $639,000

    Sold Oct 30, 2025

    41474 Charismatic Way, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,647 Sq Ft
    • Built 2015

    Last Sold Summary

    • $175/SF
    • 57 Days On Market

    Current Estimated Value $650,300

    Last Listing Agent Laura Hefley RE/MAX One

    41474 Charismatic Way, Leonardtown, MD 20650
  • /91

    $720,000

    Sold Jun 26, 2026

    41395 Omaha Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,367 Sq Ft
    • Built 2012

    Last Sold Summary

    • 1% Above List Price
    • $165/SF
    • 1 Day On Market

    Current Estimated Value $711,947

    Last Listing Agent Andrew Shemeta CENTURY 21 New Millennium

    41395 Omaha Ct, Leonardtown, MD 20650
  • /90

    $575,000

    Sold Mar 05, 2026

    21060 Woodmere Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,075 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Above List Price
    • $187/SF
    • 18 Days On Market

    Current Estimated Value $574,309

    Last Listing Agent Sharon Cox Century 21 Redwood Realty

    21060 Woodmere Dr, Leonardtown, MD 20650
  • /50

    $459,900

    Sold Jun 17, 2026

    40810 Meadow Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • Built 1963

    Last Sold Summary

    • $336/SF
    • 14 Days On Market

    Current Estimated Value $453,935

    Last Listing Agent Cheryl Bare CENTURY 21 New Millennium

    40810 Meadow Dr, Leonardtown, MD 20650
  • /59

    $600,000

    Sold Oct 01, 2025

    43571 Bayberry Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • Built 1993

    Last Sold Summary

    • $204/SF
    • 22 Days On Market

    Current Estimated Value $614,828

    Last Listing Agent Jenny Norris EXP Realty, LLC

    43571 Bayberry Ct, Leonardtown, MD 20650
  • /18

    $570,000

    Sold Apr 16, 2026

    43641 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,184 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Below List Price
    • $261/SF
    • 0 Days On Market

    Current Estimated Value $571,870

    Last Listing Agent Jimmy Hayden RE/MAX One

    43641 Redmond Rd, Leonardtown, MD 20650
  • /3

    $310,000

    Sold Apr 17, 2026

    39725 Lady Baltimore Ave, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Below List Price
    • $164/SF
    • 4 Days On Market

    Current Estimated Value $361,918

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    39725 Lady Baltimore Ave, Leonardtown, MD 20650
  • /64

    $865,000

    Sold May 28, 2026

    40171 Little Woods Ln, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,586 Sq Ft
    • Built 1954

    Last Sold Summary

    • 1% Below List Price
    • $334/SF
    • 6 Days On Market

    Current Estimated Value $858,663

    Last Listing Agent Barbara Blades CENTURY 21 New Millennium

    40171 Little Woods Ln, Leonardtown, MD 20650
  • /54

    $510,000

    Sold Dec 22, 2025

    41535 Singletree Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft
    • Built 2002

    Last Sold Summary

    • $225/SF
    • 44 Days On Market

    Current Estimated Value $518,609

    Last Listing Agent Karen Taylor JPAR Real Estate Professionals

    41535 Singletree Dr, Leonardtown, MD 20650
  • /48

    $447,400

    Sold Oct 09, 2025

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft
    • Built 2025

    Last Sold Summary

    • $175/SF
    • 58 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 87-23670 Dragonfly Ln, Leonardtown, MD 20650
  • /2

    $400,000

    Sold Aug 18, 2025

    22190 Bull Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 1987

    Last Sold Summary

    • $290/SF

    Current Estimated Value $403,683

    Last Listing Agent Gabriela Montgomery RE/MAX Realty Group

    22190 Bull Rd, Leonardtown, MD 20650
  • /30

    $479,900

    Sold May 29, 2026

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 35 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 102 - 23707 Dragonfly Ln, Leonardtown, MD 20650
  • /16

    $281,650

    Sold Sep 30, 2025

    43658 Redmond Rd, Leonardtown, MD 20650

    • 4 Beds
    • 1.5 Baths
    • 2,078 Sq Ft
    • Built 1959

    Last Sold Summary

    • $136/SF
    • 12 Days On Market

    Current Estimated Value $320,501

    Last Listing Agent Candide Rayle CENTURY 21 New Millennium

    43658 Redmond Rd, Leonardtown, MD 20650
  • /49

    $447,400

    Sold Dec 11, 2025

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650
  • /55

    $430,000

    Sold Dec 01, 2025

    22592 Quiet Ln, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1991

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $429,289

    Last Listing Agent Paul Bell NOVA Brokers, LLC.

    22592 Quiet Ln, Leonardtown, MD 20650
  • /42

    $555,000

    Sold Sep 26, 2025

    21137 Marigold St, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,382 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 6 Days On Market

    Current Estimated Value $559,365

    Last Listing Agent Shem varhaftik District Pro Realty

    21137 Marigold St, Leonardtown, MD 20650
  • /2

    $959,600

    Sold Aug 13, 2025

    40557 Breton Knolls Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $282/SF

    Current Estimated Value $868,569

    Last Listing Agent Michele Posey RE/MAX Realty Group

    40557 Breton Knolls Ct, Leonardtown, MD 20650
  • /2

    $400,000

    Sold Jun 15, 2026

    39944 Lady Baltimore Ave, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 2,169 Sq Ft
    • Built 1997

    Last Sold Summary

    • 1% Above List Price
    • $184/SF
    • 7 Days On Market

    Current Estimated Value $403,646

    Last Listing Agent Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
  • /46

    $439,900

    Sold Mar 31, 2026

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 74 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650
  • /40

    $485,900

    Sold Apr 28, 2026

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 1% Above List Price

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 108- 23666 Weeping Willow Way, Leonardtown, MD 20650
  • /41

    $458,550

    Sold Feb 26, 2026

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • Built 2025

    Last Sold Summary

    • 78 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650
  • /88

    $1,052,000

    Sold Feb 25, 2026

    22164 Miller Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • Built 1988

    Last Sold Summary

    • 8% Above List Price
    • $390/SF
    • 7 Days On Market

    Current Estimated Value $1,037,772

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, Leonardtown, MD 20650
  • /47

    $489,900

    Sold Jun 30, 2026

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Last Sold Summary

    • $158/SF

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 117 - 23720 Weeping Willow Way, Leonardtown, MD 20650
  • /9

    $340,000

    Sold Feb 20, 2026

    22820 Duke St, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft
    • Built 1947

    Last Sold Summary

    • 3% Below List Price
    • $239/SF
    • 0 Days On Market

    Current Estimated Value $334,270

    Last Listing Agent Laura Lopez RE/Max Experience

    22820 Duke St, Leonardtown, MD 20650
  • /27

    $515,000

    Sold Aug 15, 2025

    20755 Deer Wood Park Dr, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,538 Sq Ft
    • Built 1996

    Last Sold Summary

    • $203/SF
    • 10 Days On Market

    Current Estimated Value $546,398

    Last Listing Agent Ebon Jackson EbonAries Realty Group, LLC.

    20755 Deer Wood Park Dr, Leonardtown, MD 20650
  • /75

    $640,000

    Sold Dec 01, 2025

    22216 Hanover Dr, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 4,206 Sq Ft
    • Built 2005

    Last Sold Summary

    • $152/SF
    • 1 Day On Market

    Current Estimated Value $646,383

    Last Listing Agent Christina Reed RE/MAX One

    22216 Hanover Dr, Leonardtown, MD 20650
  • /53

    $645,900

    Sold Feb 26, 2026

    23581 Gallent Fox Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,736 Sq Ft
    • Built 2009

    Last Sold Summary

    • $173/SF
    • 42 Days On Market

    Current Estimated Value $647,141

    Last Listing Agent Laura Hefley RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
  • /87

    $475,203

    Sold Mar 02, 2026

    20697 Chingville Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,458 Sq Ft
    • Built 1948

    Last Sold Summary

    • $193/SF
    • 1 Day On Market

    Current Estimated Value $478,611

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    20697 Chingville Rd, Leonardtown, MD 20650
  • /39

    $720,000

    Sold May 11, 2026

    21335 Fairwood Ct, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 4,533 Sq Ft
    • Built 2011

    Last Sold Summary

    • 1% Above List Price
    • $159/SF
    • 3 Days On Market

    Current Estimated Value $715,769

    Last Listing Agent Deanna Rothstein RE/MAX One

    21335 Fairwood Ct, Leonardtown, MD 20650
  • /48

    $469,900

    Sold Sep 18, 2025

    23664 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    23664 Dragonfly Ln, Leonardtown, MD 20650
  • /50

    $537,500

    Sold Sep 05, 2025

    41412 Doctors Crossing Rd, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,686 Sq Ft
    • Built 2019

    Last Sold Summary

    • $200/SF
    • 67 Days On Market

    Current Estimated Value $542,698

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
  • /46

    $447,400

    Sold Dec 16, 2025

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft
    • Built 2025

    Last Sold Summary

    • $172/SF
    • 90 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 88 - 23676 Dragonfly Ln, Leonardtown, MD 20650
  • /83

    $660,000

    Sold Jul 14, 2026

    41531 Kalitan Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,570 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Below List Price
    • $185/SF
    • 4 Days On Market

    Current Estimated Value $662,993

    Last Listing Agent Heather Foster RE/MAX One

    41531 Kalitan Ln, Leonardtown, MD 20650
  • /76

    $580,000

    Sold Mar 23, 2026

    23593 Mitchell Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 2,940 Sq Ft
    • Built 2004

    Last Sold Summary

    • $197/SF
    • 15 Days On Market

    Current Estimated Value $581,397

    Last Listing Agent Heather Foster RE/MAX One

    23593 Mitchell Dr, Leonardtown, MD 20650

Showing Results 1 - 40, Page 1 of 6

Frequently Asked Questions

What is the average home price in Leonardtown, MD?
Homes for sale in Leonardtown, MD have an average home price of $591,234.
What is the average time to sell a house in Leonardtown, MD?
The houses for sale in Leonardtown, MD spend an average of 43 days on the market.
What is the number of active homes for sale in Leonardtown, MD?
There are 40 active homes for sale in Leonardtown, MD.
How many homes have sold over the last 12 months in Leonardtown, MD?
195 homes have sold in Leonardtown, MD over the last 12 months.

Home Price Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$599,000
Median Townhouse Sale Price
$454,900
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$191
Number of Homes for Sale
40
Last 12 months Home Sales
195
Months of Supply
2.50
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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