6,994

Homes in ZIP Code 20650

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  • /48

    $479,900

    Sold Jun 17, 2026

    Lot 113 - 23696 Weeping Willow Way, Leonardtown, MD 20650

    • 4 Beds
    • 3.5 Baths

    Last Sold Summary

    Last Listing Agent Laura Lee Hefley RE/MAX One

    Lot 113 - 23696 Weeping Willow Way, 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

  • /41

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    41888 Jenkins Ct, Leonardtown, MD 20650

    Interior Photos Coming Soon! Expected on market date is Sept 1, 2026Welcome to 41888 Jenkins Court in the highly desirable Academy Hills community of Leonardtown! Perfectly situated within walking distance of the Leonardtown Wharf and historic Leonardtown Square, this exceptional home places you just moments from charming shops, local dining, breweries, community events, and all that downtown

    Wayne & Christine Floyd RE/MAX Realty Group

    41888 Jenkins Ct, Leonardtown, MD 20650
  • /54

    $485,000

    Sold Jul 02, 2026

    21807 Potomac View Dr, Leonardtown, MD 20650

    • 4 Beds
    • 3 Baths
    • 2,019 Sq Ft
    • Built 1965

    Last Sold Summary

    • $240/SF
    • 2 Days On Market

    Current Estimated Value $483,031

    Last Listing Agent Diana Washabaugh CENTURY 21 New Millennium

    21807 Potomac View Dr, 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

  • /2

    $614,900

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,736 Sq Ft

    23354 Lindsay Dr, Leonardtown, MD 20650

    Welcome to this stunning rambler in the highly sought-after community of Clark's Rest! Thoughtfully designed with 9' ceilings, quartz countertops, designer finishes, and upgrades throughout, this home offers the perfect blend of style, comfort, and functionality.The main level features three spacious bedrooms and two full bathrooms, including a beautiful owner's suite with dual vanities. The

    Dorothy Bistransin Redfin Corp

    23354 Lindsay Dr, Leonardtown, MD 20650
  • /25

    $315,000

    Sold May 28, 2026

    22175 Bayside Rd, Leonardtown, MD 20650

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • Built 1967

    Last Sold Summary

    • $264/SF
    • 55 Days On Market

    Current Estimated Value $314,435

    Last Listing Agent Darrin Carter RE/MAX One

    22175 Bayside Rd, 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

  • /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
  • /48

    $989,000

    Sold Sep 03, 2026

    22856 White Swan Way, Leonardtown, MD 20650

    • 5 Beds
    • 5 Baths
    • 5,810 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $170/SF
    • 43 Days On Market

    Current Estimated Value $1,021,904

    Last Listing Agent Barbara Stellway KW Metro Center

    22856 White Swan Way, 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

  • /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
  • /79

    $669,900

    Sold Jun 18, 2026

    41249 Brenda Ct, Leonardtown, MD 20650

    • 3 Beds
    • 2.5 Baths
    • 3,098 Sq Ft
    • Built 1987

    Last Sold Summary

    • $216/SF
    • 27 Days On Market

    Current Estimated Value $669,060

    Last Listing Agent Robin Errington CENTURY 21 New Millennium

    41249 Brenda Ct, 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

  • /59

    $765,000

    $15K PRICE INCREASE
    • 5 Beds
    • 4 Baths
    • 4,873 Sq Ft

    41402 Omaha Ct, Leonardtown, MD 20650

    2.25% Assumable VA loan & one of the largest lots in Leonard's Grant at .64 acres! This brilliant Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Lots of fruit trees (Fig, Apple, Mulberry, Dwarf Peach, Pear, Strawberry and Persimmon). Enter to find gorgeous exotic hardwood tigerwood floors flowing seamlessly across the main level into the

    Jonathan Powell Real Broker, LLC

    41402 Omaha Ct, 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
    • /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

  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /40

    $559,900

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

    23636 Gunnell Dr, Leonardtown, MD 20650

    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, move-in-ready feel.

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, 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
    • /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

  • /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
  • /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
    • /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

  • /74

    $690,000

    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of Leonardtown’s most desirable neighborhoods. Tucked near the end of a quiet street by the cul-de-sac, this 4-bedroom, 3.5-bath home offers more than 3,500 square feet of finished living space, a finished basement, and a large, level backyard with room to truly enjoy.Inside, a bright and

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, 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
    • /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

  • /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
  • /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

Showing Results 161 - 200, Page 5 of 18

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