6,740

Leonardtown, MD Homes

Section Image Section Image
  • /22

    $300,000

    • Land
    • 1.51 Acres
    • $198,675 per Acre

    41708 Fenwick St, Leonardtown, MD 20650

    Discover a rare opportunity to create your dream home just moments from the charm and culture of Leonardtown Historic Art District. Ideally situated within walking distance to local shops, dining, the scenic Leonardtown Wharf, and the United States Postal Service. This property offers the perfect balance of privacy and community living. Conveniently located within walking distance of highly rated

    Tig Wright Redfin Corp

    41708 Fenwick St, 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
    • /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

  • /82

    $701,650

    Sold Sep 11, 2025

    22064 Daffodil Ct, Leonardtown, MD 20650

    • 6 Beds
    • 4.5 Baths
    • 5,012 Sq Ft
    • Built 2022

    Last Sold Summary

    • $140/SF
    • 43 Days On Market

    Current Estimated Value $732,039

    Last Listing Agent Laura Lee Hefley RE/MAX One

    22064 Daffodil Ct, 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

  • /57

    $659,000

    $41K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    42195 White Point Beach Rd, Leonardtown, MD 20650

    Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still

    Carl Franzen Franzen Realtors, Inc.

    42195 White Point Beach Rd, 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 $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

  • /12

    $550,000

    Coming Soon
    • 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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /46

    $489,900

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 132 - 23697 Weeping Willow Way, Leonardtown, MD 20650

    Homesite 132 TO BE BUILT New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland 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 3095 sq ft home offers generous living areas, abundant natural light, and

    Laura Lee Hefley RE/MAX One

    Lot 132 - 23697 Weeping Willow Way, 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
    • /46

      Est $925,774

      Not Listed For Sale

      40472 Port Place, Leonardtown, MD 20650

      • 4 Beds
      • 3 Baths
      • 2,828 Sq Ft
      • Built 1972
      40472 Port Place, Leonardtown, MD 20650

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Sean Escobar O'Brien Realty ERA Powered

  • /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
    • /22

      Est $414,054

      Not Listed For Sale

      42454 Wilderness Rd, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,388 Sq Ft
      • Built 1994
      42454 Wilderness Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Jimmy Hayden 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
    • /37

      Est $547,942

      Not Listed For Sale

      40222 Breton Beach Rd, Leonardtown, MD 20650

      • 2 Beds
      • 1 Bath
      • 1,296 Sq Ft
      • Built 1976
      40222 Breton Beach Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 207 Days On Market

      Last Listing Agent Jake Grier Baldus Real Estate, Inc.

  • /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
    • /48

      Est $433,790

      Not Listed For Sale

      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      • 3 Beds
      • 3 Baths
      • 3,692 Sq Ft
      • Built 1961
      42798 Saint Andrews Church Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Leonard Ferris Coldwell Banker Premier

  • /70

    $399,000

    • 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
    • /83

      Est $546,062

      Not Listed For Sale

      41936 Kentucky Ct, Leonardtown, MD 20650

      • 5 Beds
      • 3.5 Baths
      • 4,115 Sq Ft
      • Built 2002
      41936 Kentucky Ct, Leonardtown, MD 20650

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Jessica Raley CENTURY 21 New Millennium

  • /40

    $579,900

    $20K 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 comfortable living space on a beautifully maintained 0.51-acre lot.Step inside to discover fresh updates, including new carpet and luxury vinyl plank flooring, creating a move-in ready home with a modern feel. The thoughtfully designed floor plan provides ample room for

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • /113

    $638,000

    Sold Aug 12, 2025

    23275 Jenifer Ct, Leonardtown, MD 20650

    • 5 Beds
    • 4.5 Baths
    • 6,311 Sq Ft
    • Built 2005

    Last Sold Summary

    • $101/SF
    • 86 Days On Market

    Current Estimated Value $667,952

    Last Listing Agent Jennifer Goddard CENTURY 21 New Millennium

    23275 Jenifer Ct, Leonardtown, MD 20650
    • /54

      Est $606,476

      Not Listed For Sale

      20370 Chingville Rd, Leonardtown, MD 20650

      • 4 Beds
      • 3.5 Baths
      • 3,538 Sq Ft
      • Built 2007
      20370 Chingville Rd, Leonardtown, MD 20650

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Christina Reed RE/MAX One

  • /29

    $329,900

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    22332 Cedar St, Leonardtown, MD 20650

    Quaint All-Brick Rambler in a Water-Oriented Community This well-built, all-brick rambler offers timeless charm and solid construction. Features include a gas furnace, central air conditioning, and hardwood floors beneath the new carpeting. The interior has been freshly painted and includes a bright eat-in kitchen. Oversized two car garage with large workshop area & pull down stairs to attic

    Carol Kalmus-Choporis Century 21 Redwood Realty

    22332 Cedar St, 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
    • /61

      Est $725,947

      Not Listed For Sale

      22425 Archer St, Leonardtown, MD 20650

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft
      • Built 1973
      22425 Archer St, Leonardtown, MD 20650

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kimberly Scott RE/MAX Realty Group

  • /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
    • /35

      Est $558,623

      Not Listed For Sale

      23571 Gunnell Dr, Leonardtown, MD 20650

      • 4 Beds
      • 2.5 Baths
      • 2,652 Sq Ft
      • Built 2005
      23571 Gunnell Dr, Leonardtown, MD 20650

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Alicia Guinn RE/MAX Executive

  • /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

Showing Results 161 - 200, Page 5 of 18

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