7,080

Homes in ZIP Code 20650

Section Image
  • 20753 Chestnut Ridge Dr, Leonardtown, MD 20650
    20753 Chestnut Ridge Dr, Leonardtown, MD 20650
    20753 Chestnut Ridge Dr, 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
    • 22925 Downs Cir, Leonardtown, MD 20650
      22925 Downs Cir, Leonardtown, MD 20650
      22925 Downs Cir, Leonardtown, MD 20650
      /38

      Est $381,102

      Not Listed For Sale

      22925 Downs Cir, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,904 Sq Ft
      • Built 1977
      22925 Downs Cir, Leonardtown, MD 20650

      Last Sold Summary

      • 0 Days On Market

  • 23080 Town Run Dr, Leonardtown, MD 20650
    23080 Town Run Dr, Leonardtown, MD 20650
    23080 Town Run 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
    • 22430 Hood Ln, Leonardtown, MD 20650
      22430 Hood Ln, Leonardtown, MD 20650
      22430 Hood Ln, Leonardtown, MD 20650
      /117

      Est $879,727

      Not Listed For Sale

      22430 Hood Ln, Leonardtown, MD 20650

      • 6 Beds
      • 5 Baths
      • 5,026 Sq Ft
      • Built 2005
      22430 Hood Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

  • 21784 Potomac View Dr, Leonardtown, MD 20650
    21784 Potomac View 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
    • 23603 Abraham Dr, Leonardtown, MD 20650
      23603 Abraham Dr, Leonardtown, MD 20650
      23603 Abraham Dr, Leonardtown, MD 20650
      /83

      Est $591,244

      Not Listed For Sale

      23603 Abraham Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,000 Sq Ft
      • Built 2004
      23603 Abraham Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 23 Days On Market

  • 24554 Pin Cushion Rd, Leonardtown, MD 20650
    24554 Pin Cushion Rd, 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
    • 42443 Dean Forest Ct, Leonardtown, MD 20650
      42443 Dean Forest Ct, Leonardtown, MD 20650
      42443 Dean Forest Ct, Leonardtown, MD 20650
      /64

      Est $635,911

      Not Listed For Sale

      42443 Dean Forest Ct, Leonardtown, MD 20650

      • 4 Beds
      • 4.5 Baths
      • 4,816 Sq Ft
      • Built 2005
      42443 Dean Forest Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 70 Days On Market

  • 23330 Lindsay Dr, Leonardtown, MD 20650
    23330 Lindsay Dr, Leonardtown, MD 20650
    23330 Lindsay Dr, 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
    • 44403 Medleys Neck Rd, Leonardtown, MD 20650
      44403 Medleys Neck Rd, Leonardtown, MD 20650
      44403 Medleys Neck Rd, Leonardtown, MD 20650
      /59

      Est $572,492

      Not Listed For Sale

      44403 Medleys Neck Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 2,647 Sq Ft
      • Built 1992
      44403 Medleys Neck Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

  • 20255 Hawks Way, Leonardtown, MD 20650
    20255 Hawks Way, Leonardtown, MD 20650
    /2

    $700,000

    Sold Apr 27, 2026

    20255 Hawks Way, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 2026

    Last Sold Summary

    • $292/SF

    Last Listing Agent Mark Frisco CENTURY 21 New Millennium

    20255 Hawks Way, Leonardtown, MD 20650
    • 22717 Point Lookout Rd, Leonardtown, MD 20650
      22717 Point Lookout Rd, Leonardtown, MD 20650
      22717 Point Lookout Rd, Leonardtown, MD 20650
      /26

      Est $299,747

      Not Listed For Sale

      22717 Point Lookout Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,243 Sq Ft
      • Built 1947
      22717 Point Lookout Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 17 Days On Market

  • 21390 Little Saint Annes Ln, Leonardtown, MD 20650
    21390 Little Saint Annes Ln, Leonardtown, MD 20650
    21390 Little Saint Annes Ln, Leonardtown, MD 20650
    /95

    $753,000

    Sold Jun 05, 2026

    21390 Little Saint Annes Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • Built 2003

    Last Sold Summary

    • 12% Above List Price
    • $215/SF
    • 2 Days On Market

    Current Estimated Value $662,859

    Last Listing Agent Jan Barnes CENTURY 21 New Millennium

    21390 Little Saint Annes Ln, Leonardtown, MD 20650
    • 42287 Bird Haven Dr, Leonardtown, MD 20650
      42287 Bird Haven Dr, Leonardtown, MD 20650
      42287 Bird Haven Dr, Leonardtown, MD 20650
      /54

      Est $571,079

      Not Listed For Sale

      42287 Bird Haven Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,608 Sq Ft
      • Built 2003
      42287 Bird Haven Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • 23433 Grovewood Ct, Leonardtown, MD 20650
    23433 Grovewood Ct, Leonardtown, MD 20650
    23433 Grovewood Ct, Leonardtown, MD 20650
    /78

    $519,000

    Sold Jul 01, 2025

    23433 Grovewood Ct, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,804 Sq Ft
    • Built 2022

    Last Sold Summary

    • $185/SF
    • 3 Days On Market

    Current Estimated Value $515,409

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

    23433 Grovewood Ct, Leonardtown, MD 20650
    • 42921 Hungerford Ct, Hollywood, MD 20636
      42921 Hungerford Ct, Hollywood, MD 20636
      42921 Hungerford Ct, Hollywood, MD 20636
      /47

      Est $736,413

      Not Listed For Sale

      42921 Hungerford Ct, Hollywood, MD 20636

      • 4 Beds
      • 3.5 Baths
      • 3,929 Sq Ft
      • Built 1999
      42921 Hungerford Ct, Hollywood, MD 20636

      Last Sold Summary

      • 3 Days On Market

  • 21130 Someday Farm Ln, Leonardtown, MD 20650
    21130 Someday Farm Ln, Leonardtown, MD 20650
    21130 Someday Farm Ln, Leonardtown, MD 20650
    /96

    $880,000

    Sold Jun 19, 2026

    21130 Someday Farm Ln, Leonardtown, MD 20650

    • 5 Beds
    • 2.5 Baths
    • 3,122 Sq Ft
    • Built 2011

    Last Sold Summary

    • 10% Above List Price
    • $282/SF
    • 6 Days On Market

    Current Estimated Value $798,863

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    21130 Someday Farm Ln, Leonardtown, MD 20650
    • 21733 Pinehurst Ct, Leonardtown, MD 20650
      21733 Pinehurst Ct, Leonardtown, MD 20650
      21733 Pinehurst Ct, Leonardtown, MD 20650
      /91

      Est $558,936

      Not Listed For Sale

      21733 Pinehurst Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,602 Sq Ft
      • Built 1990
      21733 Pinehurst Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

  • 44504 Watson Ln, Leonardtown, MD 20650
    44504 Watson Ln, Leonardtown, MD 20650
    44504 Watson Ln, Leonardtown, MD 20650
    /36

    $465,000

    Sold Nov 21, 2025

    44504 Watson Ln, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,304 Sq Ft
    • Built 2003

    Last Sold Summary

    • $202/SF
    • 17 Days On Market

    Current Estimated Value $474,072

    Last Listing Agent Danny Morris O'Brien Realty ERA Powered

    44504 Watson Ln, Leonardtown, MD 20650
    • 22266 Orchard Ct, Leonardtown, MD 20650
      22266 Orchard Ct, Leonardtown, MD 20650
      22266 Orchard Ct, Leonardtown, MD 20650
      /37

      Est $581,637

      Not Listed For Sale

      22266 Orchard Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,366 Sq Ft
      • Built 2003
      22266 Orchard Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • 41460 Challedon Way, Leonardtown, MD 20650
    41460 Challedon Way, Leonardtown, MD 20650
    /2

    $630,000

    Sold Aug 20, 2025

    41460 Challedon Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 3,252 Sq Ft
    • Built 2010

    Last Sold Summary

    • $194/SF
    • 2 Days On Market

    Current Estimated Value $630,163

    Last Listing Agent Heather Foster RE/MAX One

    41460 Challedon Way, Leonardtown, MD 20650
    • 42512 Dean Forest Way, Leonardtown, MD 20650
      42512 Dean Forest Way, Leonardtown, MD 20650
      42512 Dean Forest Way, Leonardtown, MD 20650
      /49

      Est $596,870

      Not Listed For Sale

      42512 Dean Forest Way, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2004
      42512 Dean Forest Way, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

  • 0 Kiskadee Ln, Leonardtown, MD 20650
    0 Kiskadee Ln, Leonardtown, MD 20650
    0 Kiskadee Ln, Leonardtown, MD 20650
    /18

    $175,000

    Sold Feb 02, 2026

    0 Kiskadee Ln, Leonardtown, MD 20650

    • Land
    • 3.53 Acres
    • $49,575 per Acre

    Last Sold Summary

    • 156 Days On Market

    Last Listing Agent Pattee McInerney Scott McInerney RE/MAX One

    0 Kiskadee Ln, Leonardtown, MD 20650
    • 21871 Fairway Dr, Leonardtown, MD 20650
      21871 Fairway Dr, Leonardtown, MD 20650
      21871 Fairway Dr, Leonardtown, MD 20650
      /44

      Est $645,393

      Not Listed For Sale

      21871 Fairway Dr, Leonardtown, MD 20650

      • 6 Beds
      • 3.5 Baths
      • 3,332 Sq Ft
      • Built 1997
      21871 Fairway Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 16 Days On Market

  • 23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    23558 Belmar Dr, Leonardtown, MD 20650
    /88

    $685,000

    Sold Jul 10, 2025

    23558 Belmar Dr, Leonardtown, MD 20650

    • 6 Beds
    • 3.5 Baths
    • 4,267 Sq Ft
    • Built 2008

    Last Sold Summary

    • $161/SF

    Current Estimated Value $685,707

    Last Listing Agent Heather Foster RE/MAX One

    23558 Belmar 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 $347,004

      Not Listed For Sale

      39834 Big Pine Trail, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1999
      39834 Big Pine Trail, Leonardtown, MD 20650

      Last Sold Summary

      • 130 Days On Market

  • 22362 Armstrong Dr, Leonardtown, MD 20650
    22362 Armstrong Dr, Leonardtown, MD 20650
    22362 Armstrong Dr, Leonardtown, MD 20650
    /32

    $425,000

    Sold Oct 22, 2025

    22362 Armstrong Dr, Leonardtown, MD 20650

    • 3 Beds
    • 3 Baths
    • 2,028 Sq Ft
    • Built 1973

    Last Sold Summary

    • 10% Below List Price
    • $210/SF
    • 207 Days On Market

    Current Estimated Value $420,883

    Last Listing Agent Chris Hill CENTURY 21 New Millennium

    22362 Armstrong Dr, Leonardtown, MD 20650
    • 22135 Cartwright Rd, Leonardtown, MD 20650
      22135 Cartwright Rd, Leonardtown, MD 20650
      22135 Cartwright Rd, Leonardtown, MD 20650
      /30

      Est $459,139

      Not Listed For Sale

      22135 Cartwright Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2.5 Baths
      • 1,836 Sq Ft
      • Built 1991
      22135 Cartwright Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 115 Days On Market

  • 42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    /50

    $520,000

    Sold Feb 17, 2026

    42043 Starlight Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft
    • Built 2004

    Last Sold Summary

    • $210/SF
    • 119 Days On Market

    Current Estimated Value $528,955

    Last Listing Agent Kimberly St. Laurent RE/MAX One

    42043 Starlight Dr, Leonardtown, MD 20650
    • 21104 Rosebay Way, Leonardtown, MD 20650
      21104 Rosebay Way, Leonardtown, MD 20650
      21104 Rosebay Way, Leonardtown, MD 20650
      /99

      Est $621,877

      Not Listed For Sale

      21104 Rosebay Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,680 Sq Ft
      • Built 2003
      21104 Rosebay Way, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650
    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650
    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650
    /40

    $497,400

    Sold May 12, 2026

    Lot 133 - 23691 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 2% Above List Price

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 133 - 23691 Weeping Willow Way, 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 $450,363

      Not Listed For Sale

      21764 Potomac View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 2,264 Sq Ft
      • Built 1986
      21764 Potomac View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 3 Days On Market

  • Lot 97- 23730 Dragonfly Ln, Leonardtown, MD 20650
    Lot 97- 23730 Dragonfly Ln, Leonardtown, MD 20650
    Lot 97- 23730 Dragonfly Ln, Leonardtown, MD 20650
    /58

    $459,900

    Sold Nov 25, 2025

    Lot 97- 23730 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    • 18 Days On Market

    Last Listing Agent Laura Hefley RE/MAX One

    Lot 97- 23730 Dragonfly Ln, Leonardtown, MD 20650
    • 23255 Hollywood Rd, Leonardtown, MD 20650
      23255 Hollywood Rd, Leonardtown, MD 20650
      23255 Hollywood Rd, Leonardtown, MD 20650
      /42

      Est $339,318

      Not Listed For Sale

      23255 Hollywood Rd, Leonardtown, MD 20650

      • 3 Beds
      • 1.5 Baths
      • 1,584 Sq Ft
      • Built 1930
      23255 Hollywood Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

  • 21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    21925 Budds Creek Rd, Leonardtown, MD 20650
    /31

    $465,000

    Sold Feb 11, 2026

    21925 Budds Creek Rd, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,527 Sq Ft
    • Built 1970

    Last Sold Summary

    • $184/SF
    • 72 Days On Market

    Current Estimated Value $462,683

    Last Listing Agent Jimmy Hayden RE/MAX One

    21925 Budds Creek Rd, Leonardtown, MD 20650
    • 40883 Meadow Dr, Leonardtown, MD 20650
      40883 Meadow Dr, Leonardtown, MD 20650
      40883 Meadow Dr, Leonardtown, MD 20650
      /95

      Est $563,077

      Not Listed For Sale

      40883 Meadow Dr, Leonardtown, MD 20650

      • 5 Beds
      • 3 Baths
      • 2,264 Sq Ft
      • Built 1980
      40883 Meadow Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 39 Days On Market

  • 20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    20591 Chestnut Ridge Dr, Leonardtown, MD 20650
    /41

    $599,900

    Sold Oct 30, 2025

    20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 3,061 Sq Ft
    • Built 1995

    Last Sold Summary

    • $196/SF
    • 94 Days On Market

    Current Estimated Value $619,384

    Last Listing Agent Lauren Garner EXP Realty, LLC

    20591 Chestnut Ridge 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 $617,809

      Not Listed For Sale

      43225 Prince Pine Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,960 Sq Ft
      • Built 1992
      43225 Prince Pine Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 27 Days On Market

  • 20752 Penansey Ln, Leonardtown, MD 20650
    20752 Penansey Ln, Leonardtown, MD 20650
    /2

    $750,000

    Sold May 28, 2026

    20752 Penansey Ln, Leonardtown, MD 20650

    • 5 Beds
    • 3.5 Baths
    • 2,936 Sq Ft
    • Built 2010

    Last Sold Summary

    • $255/SF
    • 0 Days On Market

    Current Estimated Value $745,686

    Last Listing Agent Heather Foster RE/MAX One

    20752 Penansey Ln, Leonardtown, MD 20650
    • 40721 Merlin Way, Leonardtown, MD 20650
      40721 Merlin Way, Leonardtown, MD 20650
      40721 Merlin Way, Leonardtown, MD 20650
      /109

      Est $669,260

      Not Listed For Sale

      40721 Merlin Way, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 2,469 Sq Ft
      • Built 2002
      40721 Merlin Way, Leonardtown, MD 20650

      Last Sold Summary

      • 110 Days On Market

Showing Results 321 - 360, Page 9 of 18

Maryland St Marys County Leonardtown 20650

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group