221

Recently Sold Homes in 20650

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
  • /96

    $1,300,000

    Sold Nov 13, 2025

    23155 Greenstone Dr, 3, Leonardtown, MD 20650

    • 6 Beds
    • 3.5 Baths
    • 5,888 Sq Ft
    • Built 2020

    Last Sold Summary

    • $221/SF
    • 63 Days On Market

    Current Estimated Value $1,219,870

    Last Listing Agent Jimmy Hayden RE/MAX One

    23155 Greenstone Dr, 3, 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
  • /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
  • /18

    $11,500

    Sold Apr 20, 2026

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636

    • Land
    • 1.23 Acres
    • $9,350 per Acre

    Last Sold Summary

    • 77% Below List Price
    • 57 Days On Market

    Last Listing Agent Joseph Hawkins Hawkins Real Estate Company

    0 Hollywood Rd Unit MDSM2029210, Hollywood, MD 20636
  • /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

Showing Results 1 - 40, Page 1 of 6

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