6,720

Leonardtown, MD Homes

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    • /23

      Est $335,260

      Not Listed For Sale

      23028 Hopton Ln, Leonardtown, MD 20650

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1988
      23028 Hopton Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Emily Gross EXP Realty, LLC

  • /17

    $3,800,000

    Pending
    • Land
    • 52.18 Acres
    • $72,825 per Acre

    0 Cedar Lane Rd, Leonardtown, MD 20650

    This property offers the perfect blend of rural charm and convenient access to urban amenities. With the potential for annexation into the town of Leonardtown, there are exciting development possibilities on the horizon. Don't miss this unique opportunity!

    Carol Kalmus-Choporis Century 21 Redwood Realty

    0 Cedar Lane Rd, Leonardtown, MD 20650
  • /13

    $150,000

    Sold Apr 03, 2026

    20959 Redgate Ln, Leonardtown, MD 20650

    • 3 Beds
    • 1 Bath
    • 1,026 Sq Ft
    • Built 1961

    Last Sold Summary

    • $146/SF
    • 209 Days On Market

    Current Estimated Value $216,030

    Last Listing Agent Greg Jones Keller Williams Legacy

    20959 Redgate Ln, Leonardtown, MD 20650
    • /70

      Est $687,581

      Not Listed For Sale

      21380 Fairwood Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 3,228 Sq Ft
      • Built 2008
      21380 Fairwood Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /91

    $699,000

    $81K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 5,484 Sq Ft

    22601 Avenmar Dr, Leonardtown, MD 20650

    Welcome to Avenmar, where this spacious home is situated on a beautiful lot of over two acres, offering privacy, mature trees, and a peaceful wooded setting. Built in 2002 and largely in its original condition, the home has been well maintained and is ready for its next owner to bring their own style and updates.The main level offers a spacious, open layout with a formal dining room,

    Jennifer Goddard CENTURY 21 New Millennium

    22601 Avenmar Dr, Leonardtown, MD 20650
  • /89

    $599,900

    Sold Jun 26, 2026

    40704 Chance Way, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft
    • Built 2003

    Last Sold Summary

    • $182/SF
    • 6 Days On Market

    Current Estimated Value $599,242

    Last Listing Agent Kelly Padgett Century 21 Redwood Realty

    40704 Chance Way, Leonardtown, MD 20650
    • /87

      Est $659,121

      Not Listed For Sale

      43610 Deer Run Ct, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,980 Sq Ft
      • Built 1997
      43610 Deer Run Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /14

    $319,000

    • 3 Beds
    • 1 Bath
    • 2,068 Sq Ft

    43146 N Megan Ln, Leonardtown, MD 20650

    Looking for acreage, privacy, and freedom? Discover this 12.73 acre homestead. This mostly wooded property that offers mature trees, privacy, and zero HOA restrictions located just minutes from Leonardtown, California, Solomons Island, and Naval Air Station Patuxent River. Featuring a vintage 1953 3-bed/1-bath home which is being sold "AS IS", detached garage, and multiple outbuildings, the

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    43146 N Megan Ln, Leonardtown, MD 20650
  • /2

    $434,000

    Sold Jun 26, 2026

    41600 Miss Bessie Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 1,910 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Above List Price
    • $227/SF
    • 3 Days On Market

    Current Estimated Value $433,974

    Last Listing Agent Mike Mason Long & Foster Real Estate, Inc.

    41600 Miss Bessie Dr, Leonardtown, MD 20650
    • /42

      Est $610,484

      Not Listed For Sale

      21120 Someday Farm Ln, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,100 Sq Ft
      • Built 1990
      21120 Someday Farm Ln, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Christiana Keefer EXP Realty, LLC

  • /55

    $464,900

    Sold Oct 07, 2025

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650

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

    Last Sold Summary

    • $157/SF
    • 54 Days On Market

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 89 - 23682 Dragonfly Ln, Leonardtown, MD 20650
    • /34

      Est $364,233

      Not Listed For Sale

      20440 Chingville Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 1969
      20440 Chingville Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Michelle Camaioni RE/MAX One

  • /4

    $599,950

    Under Contract
    • 1,691 Sq Ft

    22615 Washington St, Leonardtown, MD 20650

    Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits.Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts

    Caitlin Vallandingham Infinitas Realty Group

    22615 Washington St, Leonardtown, MD 20650
  • /31

    $480,000

    Sold Nov 24, 2025

    40534 Miss Ettas Way, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2016

    Last Sold Summary

    • $271/SF
    • 82 Days On Market

    Current Estimated Value $480,621

    Last Listing Agent Connie Fitzgerald RE/MAX One

    40534 Miss Ettas Way, Leonardtown, MD 20650
    • /39

      Est $493,644

      Not Listed For Sale

      41464 Helen Marie Ct, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 2,010 Sq Ft
      • Built 1995
      41464 Helen Marie Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Josh Wilson RE/MAX One

  • /30

    $479,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650

    *** PENDING *** Homesite 159 Oakley D1 New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural

    Laura Lee Hefley RE/MAX One

    Lot 159 - 23652 Dragonfly Ln, Leonardtown, MD 20650
  • /58

    $405,000

    Sold Feb 25, 2026

    19137 Lake Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 1,308 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Above List Price
    • $310/SF

    Current Estimated Value $402,985

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    19137 Lake Dr, Leonardtown, MD 20650
    • /90

      Est $703,173

      Not Listed For Sale

      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,748 Sq Ft
      • Built 1999
      20746 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Lisa Riggleman RE/MAX One

  • /70

    $389,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    41620 Church St, Leonardtown, MD 20650

    Fully renovated. Move-in ready. Prime downtown location.Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value.Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of

    Chanel Li Evergreen Properties

    41620 Church St, Leonardtown, MD 20650
  • /82

    $727,360

    Sold May 14, 2026

    43500 Deer Run Ct, Leonardtown, MD 20650

    • 4 Beds
    • 2.5 Baths
    • 2,972 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Above List Price
    • $245/SF
    • 4 Days On Market

    Current Estimated Value $712,670

    Last Listing Agent Sarah Mulford-Martin EXP Realty, LLC

    43500 Deer Run Ct, Leonardtown, MD 20650
    • /29

      Est $415,757

      Not Listed For Sale

      40449 Breton View Dr, Leonardtown, MD 20650

      • 3 Beds
      • 3.5 Baths
      • 2,288 Sq Ft
      • Built 1995
      40449 Breton View Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Edward Tully RE/MAX One

  • /40

    $559,900

    $40K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,948 Sq Ft

    23636 Gunnell Dr, Leonardtown, MD 20650

    There's still time. Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath Colonial offers nearly 3,000 square feet of living space on a beautifully maintained 0.51-acre lot, combining comfortable everyday living with plenty of room to grow.Step inside to a bright, inviting interior featuring new carpet and luxury vinyl plank flooring, giving the home a fresh,

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • /4

    $285,500

    Sold Mar 17, 2026

    22745 Duke St, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 868 Sq Ft
    • Built 1949

    Last Sold Summary

    • 5% Below List Price
    • $329/SF
    • 0 Days On Market

    Current Estimated Value $284,398

    Last Listing Agent Jimmy Hayden RE/MAX One

    22745 Duke St, Leonardtown, MD 20650
    • /43

      Est $534,725

      Not Listed For Sale

      21108 Arbor Ct, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,412 Sq Ft
      • Built 1991
      21108 Arbor Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Cheryl Bare CENTURY 21 New Millennium

  • /41

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    23679 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D2 Natural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Taj Quartz CountertopsSplendur Cream BacksplashDeluxe Shower in Primary

    Quality Built Homes Builder
    23679 Weeping Willow Way, Leonardtown, MD 20650
  • /81

    $565,000

    Sold Jun 01, 2026

    21767 Potomac View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths
    • 4,384 Sq Ft
    • Built 1977

    Last Sold Summary

    • 2% Above List Price
    • $129/SF
    • 9 Days On Market

    Current Estimated Value $556,483

    Last Listing Agent Jessica Raley CENTURY 21 New Millennium

    21767 Potomac View Dr, Leonardtown, MD 20650
    • /19

      Est $351,136

      Not Listed For Sale

      43950 Blake Creek Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,412 Sq Ft
      • Built 1995
      43950 Blake Creek Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Karen Alford-Brooks CENTURY 21 New Millennium

  • /42

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650

    *** November Delivery ***ALMOST READY*******Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #143 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished

    Laura Lee Hefley RE/MAX One

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
  • /60

    $625,000

    Sold Nov 26, 2025

    43107 Gum Spring Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 2,742 Sq Ft
    • Built 1993

    Last Sold Summary

    • $228/SF
    • 11 Days On Market

    Current Estimated Value $626,335

    Last Listing Agent Josh Yowell EXP Realty, LLC

    43107 Gum Spring Dr, Leonardtown, MD 20650
    • /59

      Est $440,999

      Not Listed For Sale

      40781 Center 40 Cir, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,992 Sq Ft
      • Built 1967
      40781 Center 40 Cir, Leonardtown, MD 20650

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /74

    $680,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Exciting New Offer! Sellers are offering $10,000 in buyer assistance to help make this home your own! Put it toward eligible closing costs or an interest rate buydown, and keep more of your own money available for any updates you want. Ask your lender how the credit could work for you.Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • /57

    $600,000

    Sold Jun 10, 2026

    23264 Lindsay Dr, Leonardtown, MD 20650

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft
    • Built 2020

    Last Sold Summary

    • $212/SF
    • 39 Days On Market

    Current Estimated Value $595,515

    Last Listing Agent Wayne Floyd RE/MAX One

    23264 Lindsay Dr, Leonardtown, MD 20650
    • /39

      Est $698,569

      Not Listed For Sale

      21885 Newtowne Neck Rd, Leonardtown, MD 20650

      • 5 Beds
      • 4.5 Baths
      • 5,488 Sq Ft
      • Built 1999
      21885 Newtowne Neck Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Jonathan Powell Real Broker, LLC

  • /30

    $1,750,000

    $115K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft

    0 Bayside Rd, Leonardtown, MD 20650

    Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This is a beautiful, well-maintained waterfront farm that is located a few minutes from historic Downtown Leonardtown. When you enter the property gates, you will see the most beautiful canopy of trees leading you through the whole farm. The Charming Cape Cod house is situated on 48.9 acres of gorgeous land. The

    Bonnie Haley Haley Family Realty

    0 Bayside Rd, Leonardtown, MD 20650
  • /39

    $469,900

    Sold Dec 02, 2025

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 90- 23688 Dragonfly Ln, Leonardtown, MD 20650
    • /57

      Est $441,579

      Not Listed For Sale

      22106 Society Hill Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,821 Sq Ft
      • Built 1977
      22106 Society Hill Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

  • /3

    $155,000

    • Land
    • 19,166 Sq Ft
    • $352,273 per Acre

    41650 Miss Bessie Dr, Leonardtown, MD 20650

    Great building lot in the Leonardtown city limites with water and sewer available. Part of Singletree but no HOA dues. Currently staked for a house location. Property corners are not staked. See map in documents. Located across from the hospital, walking distance to down town.

    Jan Barnes CENTURY 21 New Millennium

    41650 Miss Bessie Dr, Leonardtown, MD 20650
  • /4

    $163,500

    Sold Nov 20, 2025

    21983 Point Lookout Rd, Leonardtown, MD 20650

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1960

    Last Sold Summary

    • $143/SF
    • 37 Days On Market

    Current Estimated Value $385,630

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    21983 Point Lookout Rd, Leonardtown, MD 20650
    • /53

      Est $641,369

      Not Listed For Sale

      20529 Deer Wood Park Dr, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,564 Sq Ft
      • Built 1996
      20529 Deer Wood Park Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Cynthia Crispell Century 21 Redwood Realty

Showing Results 161 - 200, Page 5 of 18

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