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 $653,153

    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 $637,348

    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 $1,439,649

    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 $962,599

    Last Listing Agent Charlotte Long EXP Realty, LLC

    40003 Tippit Rd, Leonardtown, MD 20650
  • /74

    $475,000

    Sold Jul 15, 2025

    43985 Main Way Rd, Leonardtown, MD 20650

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1973

    Last Sold Summary

    • $198/SF
    • 1 Day On Market

    Current Estimated Value $486,075

    Last Listing Agent Jennifer Mullennix CENTURY 21 New Millennium

    43985 Main Way 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 $513,756

    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 $645,659

    Last Listing Agent Laura Hefley RE/MAX One

    41474 Charismatic Way, 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 $571,306

    Last Listing Agent Sharon Cox CENTURY 21 New Millennium

    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 $452,661

    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 $608,963

    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 $574,258

    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 $342,984

    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 $867,015

    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 $513,659

    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
  • /71

    $599,900

    Sold Jun 25, 2025

    42261 Bird Haven Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,233 Sq Ft
    • Built 2002

    Last Sold Summary

    • $186/SF
    • 18 Days On Market

    Current Estimated Value $598,322

    Last Listing Agent Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, 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 $399,748

    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 $319,335

    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 $431,660

    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 $554,005

    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 $934,282

    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 $465,703

    Last Listing Agent Kimberly Hayes CENTURY 21 New Millennium

    39944 Lady Baltimore Ave, Leonardtown, MD 20650
  • /43

    $710,000

    Sold Jul 24, 2025

    21549 Point Lookout Rd, Leonardtown, MD 20650

    • 5 Beds
    • 4 Baths
    • 3,153 Sq Ft
    • Built 2001

    Last Sold Summary

    • $225/SF
    • 6 Days On Market

    Current Estimated Value $721,048

    Last Listing Agent MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, 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 $1,027,170

    Last Listing Agent Katherine Dean RE/MAX One

    22164 Miller Ct, 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 $335,513

    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 $543,005

    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 $643,261

    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 $644,187

    Last Listing Agent Laura Hefley RE/MAX One

    23581 Gallent Fox Way, Leonardtown, MD 20650
  • /82

    $574,000

    Sold Jul 24, 2025

    23075 Hollywood Rd, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 3,238 Sq Ft
    • Built 1942

    Last Sold Summary

    • $177/SF
    • 55 Days On Market

    Current Estimated Value $570,745

    Last Listing Agent Katy Galloway Century 21 Redwood Realty

    23075 Hollywood Rd, Leonardtown, MD 20650
  • /69

    $622,500

    Sold Jul 21, 2025

    21143 Catnip Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,642 Sq Ft
    • Built 2003

    Last Sold Summary

    • $236/SF
    • 16 Days On Market

    Current Estimated Value $621,545

    Last Listing Agent Melissa Rodriguez RE/MAX One

    21143 Catnip Ct, 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 $472,124

    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 $713,000

    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 $543,157

    Last Listing Agent Delaney Clarke RE/MAX United Real Estate

    41412 Doctors Crossing Rd, 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 $592,845.
What is the average time to sell a house in Leonardtown, MD?
The houses for sale in Leonardtown, MD spend an average of 44 days on the market.
What is the number of active homes for sale in Leonardtown, MD?
There are 25 active homes for sale in Leonardtown, MD.
How many homes have sold over the last 12 months in Leonardtown, MD?
193 homes have sold in Leonardtown, MD over the last 12 months.

Home Price Trends

Median Sale Price
$545,000
Median Single Family Sale Price
$595,000
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$190
Number of Homes for Sale
25
Last 12 months Home Sales
193
Months of Supply
1.60
Median List Price
$547,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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