6,717

Leonardtown, MD Homes

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    • /28

      Est $350,592 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,292 Sq Ft

      22340 Gore St, Leonardtown, MD 20650

      22340 Gore St, Leonardtown, MD 20650
  • /43

    $445,000 Sold Jul 08, 2025

    • 1,820 Sq Ft
    • $245/SF
    • 82 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1980

    40905 Knight Rd, Leonardtown, MD 20650

    Welcome to 40905 Knight Road in beautiful Leonardtown, Maryland!This charming home blends comfort and functionality with three spacious bedrooms, 2.5 baths, and a layout that’s perfect for both everyday living and entertaining.Set on a generous half-acre lot, the fully fenced backyard offers plenty of room to enjoy the outdoors. Whether you're hosting a summer barbecue or winding

    Rob Schou EXP Realty, LLC

    40905 Knight Rd, Leonardtown, MD 20650
    • /37

      Est $638,508 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,524 Sq Ft

      41625 Ferber Ct, Leonardtown, MD 20650

      41625 Ferber Ct, Leonardtown, MD 20650
  • /85

    $695,000 Sold Jul 02, 2025

    • 4,019 Sq Ft
    • $173/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    23055 Town Run Dr, Leonardtown, MD 20650

    Stunning Clarke Model by Quality Built HomesLocated in the desirable Meadows at Town Run, this 4-bedroom, 3.5-bath home offers over 4,000 square feet of living space, including a finished lower level. Built in 2021, this home is just a few years old and has been meticulously maintained.Enjoy a prime location with Duke Elementary and the library within walking distance, Downtown

    Laura Bernth RE/MAX One

    23055 Town Run Dr, Leonardtown, MD 20650
    • /11

      Est $322,859 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,232 Sq Ft

      22249 Archer St, Leonardtown, MD 20650

      22249 Archer St, Leonardtown, MD 20650
  • /70

    $625,000 Sold Jul 02, 2025

    • 3,664 Sq Ft
    • $171/SF
    • 69 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1997

    21897 Fairway Dr, Leonardtown, MD 20650

    Qualified VA buyers using their own entitlement can assume the current 2.25% VA loan.Custom-Built Beauty Overlooking Breton Bay Golf Course! Welcome to 21897 Fairway Drive, Leonardtown, MD—a stunning 5-bedroom, 2.5-bath custom-built home in the desirable Breton Bay community. This home is in impeccable condition with numerous upgrades—simply move right in and start enjoying luxury

    Matthew Burgan Infinitas Realty Group

    21897 Fairway Dr, Leonardtown, MD 20650
    • /67

      Est $592,538 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,916 Sq Ft

      23626 Abraham Dr, Leonardtown, MD 20650

      23626 Abraham Dr, Leonardtown, MD 20650
  • /78

    $519,000 Sold Jul 01, 2025

    • 2,804 Sq Ft
    • $185/SF
    • 3 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    23433 Grovewood Ct, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest Community. *OPEN HOUSE* Saturday, May 3rd from 11-2.Welcome to this beautifully maintained, "nearly-new" end-unit townhome in the desirable Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views. The chef-inspired kitchen is a dream, showcasing granite countertops, a

    Wayne & Christine Floyd RE/MAX Realty Group

    23433 Grovewood Ct, Leonardtown, MD 20650
    • /88

      Est $608,230 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,828 Sq Ft

      23689 Jm Gough Ct, Leonardtown, MD 20650

      23689 Jm Gough Ct, Leonardtown, MD 20650
  • /64

    $1,100,000 Sold Jul 01, 2025

    • 6,508 Sq Ft
    • $169/SF
    • 7 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2009

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650

    Exceptional Private Estate with Detached Efficiency Apartment, Greenhouse, & Extensive Upgrades.Beautifully maintained and thoughtfully updated, this 5 BR, 6.5 BA custom estate offers space, privacy, and versatility in a stunning setting. A long, private farm lane leads to a solar-powered gated entry and professionally landscaped grounds, including wooden and wire fencing designed with

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
    • /43

      Est $569,856 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft

      21081 Rosebay St, Leonardtown, MD 20650

      21081 Rosebay St, Leonardtown, MD 20650
  • /80

    $505,000 Sold Jun 30, 2025

    • 2,850 Sq Ft
    • $177/SF
    • 55 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2022

    41572 Briarwood Cir, Leonardtown, MD 20650

    Stunning Townhome in Clarks Rest. Welcome to this beautifully maintained, nearly-new end-unit townhome in the sought-after Clarks Rest Community in the heart of Leonardtown. Nestled among lush trees, this home offers unparalleled privacy with serene wooded views from both the rear and side.Step inside to a spacious main level featuring luxury vinyl plank flooring and a convenient bonus

    Wayne & Christine Floyd RE/MAX Realty Group

    41572 Briarwood Cir, Leonardtown, MD 20650
    • /82

      Est $570,031 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,475 Sq Ft

      22030 Cartwright Rd, Leonardtown, MD 20650

      22030 Cartwright Rd, Leonardtown, MD 20650
  • /97

    $640,000 Sold Jun 29, 2025

    • 3,635 Sq Ft
    • $176/SF
    • 10 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1999

    44114 Woodmont Dr, Leonardtown, MD 20650

    NO SHOWINGS UNTILL THE OPEN HOUSE MAY 24, SAT 11-2.Exceptional 5-Bedroom Home on 2 Acres. Welcome to this gorgeous 5-bedroom, 3.5-bath custom home, perfectly situated on a beautifully landscaped 2-acre lot. Impeccably maintained and thoughtfully designed, this property offers an ideal blend of luxury, comfort, and practicality. All five bedrooms are located on the upper level, including a

    Lori Jean Buongiovanni (Hethmon) RE/MAX Realty Group

    44114 Woodmont Dr, Leonardtown, MD 20650
    • /50

      Est $461,323 Not Listed For Sale

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

      21807 Potomac View Dr, Leonardtown, MD 20650

      21807 Potomac View Dr, Leonardtown, MD 20650
  • /34

    $615,000 Sold Jun 27, 2025

    • 3,850 Sq Ft
    • $160/SF
    • 9 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1995

    20540 Deer Wood Park Dr, Leonardtown, MD 20650

    Welcome to this beautiful contemporary colonial situated on over two private acres in the desirable community of Chestnut Hills. As you step inside, you will be greeted by three fully finished levels of warmth and comfort to include a soaring great room with walls of windows and a main level office. This thoughtfully designed home has been meticulously maintained and offers four generously

    Kelly Parks Coldwell Banker Realty

    20540 Deer Wood Park Dr, Leonardtown, MD 20650
    • /30

      Est $328,779 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,344 Sq Ft

      39790 Lady Baltimore Ave, Leonardtown, MD 20650

      39790 Lady Baltimore Ave, Leonardtown, MD 20650
  • /31

    $579,000 Sold Jun 26, 2025

    • 2,519 Sq Ft
    • $230/SF
    • 7 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2003

    42439 Dean Forest Ct, Leonardtown, MD 20650

    Welcome home to this beautiful 5 Bedroom 3.5 Bath Colonial in Leonardtown!! You will not want to miss this one! This home features a fully renovated kitchen done in 2024, includes a massive kitchen island, tons of counter space, all granite with a quartz back splash, new SS appliances, cabinets, recessed lighting. and new Porcelain kitchen floors. Beautiful Hand Scraped Hickory engineered wood

    DJ Brady EXP Realty, LLC

    42439 Dean Forest Ct, Leonardtown, MD 20650
    • /42

      Est $655,350 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft

      20708 Waterside Dr, Leonardtown, MD 20650

      20708 Waterside Dr, Leonardtown, MD 20650
  • /71

    $599,900 Sold Jun 25, 2025

    • 3,233 Sq Ft
    • $186/SF
    • 18 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2002

    42261 Bird Haven Dr, Leonardtown, MD 20650

    Welcome to this charming 4-bedroom, 3.5-bathroom home nestled in the sought-after Kingston Estates of Leonardtown. Lovingly maintained by its original owners, this house seamlessly blends comfort, convenience and tranquility.Upon entering, you're greeted by bright and airy living spaces adorned with gorgeous wood floors that flow throughout much of the main level. The heart of the home is

    Melissa Rodriguez RE/MAX One

    42261 Bird Haven Dr, Leonardtown, MD 20650
    • /57

      Est $531,387 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,689 Sq Ft

      41898 Jenkins Ct, Leonardtown, MD 20650

      41898 Jenkins Ct, Leonardtown, MD 20650
  • /17

    $685,000 Sold Jun 20, 2025

    • 2,748 Sq Ft
    • $249/SF
    • 2 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1967

    21821 Cove Ln, Leonardtown, MD 20650

    Choice location, private point on Cherry Cove with outstanding views of Cherry Cove & Breton Bay. Solid brick rambler with lots of options; generous office could easily be converted into 3rd bedroom....sun room, family room and formal living room with fireplace. Home needs updating. A stunning, private, convenient location!

    Barbara Stellway KW Metro Center

    21821 Cove Ln, Leonardtown, MD 20650
    • /21

      Est $477,082 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft

      22318 Armstrong Dr, Leonardtown, MD 20650

      22318 Armstrong Dr, Leonardtown, MD 20650
  • /75

    $465,000 Sold Jun 20, 2025

    • 2,512 Sq Ft
    • $185/SF
    • 56 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2005

    41925 Nazareth Ct, Leonardtown, MD 20650

    DESIRED SCHOOL DISTRICT, SUBDIVISION & TOWN! 3 LEVELS of SPACIOUS LIVING! This beautiful Colonial home is nestled in the highly sought-after Academy Hill subdivision of Historic Leonardtown. Sitting on an end lot that backs to trees on .27 acres, it boasts a fenced backyard with a durable 2-year-old vinyl privacy fence —an ideal setting for privacy and entertaining on your deck. The three-level

    Dawn Bell RE/MAX One

    41925 Nazareth Ct, Leonardtown, MD 20650
    • /40

      Est $631,490 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 5,100 Sq Ft

      23258 Jenifer Ct, Leonardtown, MD 20650

      23258 Jenifer Ct, Leonardtown, MD 20650
  • /65

    $600,000 Sold Jun 17, 2025

    • 3,139 Sq Ft
    • $191/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2002

    42279 Bird Haven Dr, Leonardtown, MD 20650

    Beautiful home located in the desirable Leonardtown neighborhood of Kingston, this home features 5 bedrooms and 3.5 Baths . The main level features a large kitchen with granite counter tops and stainless steel appliances, spacious family room with wood burning fireplace, a home office with built-in storage, and formal dining room. The primary suite located on the second level features a large

    Mike Jordan CENTURY 21 New Millennium

    42279 Bird Haven Dr, Leonardtown, MD 20650
    • /104

      Est $756,837 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,804 Sq Ft

      22676 Chickadee Ln, Leonardtown, MD 20650

      22676 Chickadee Ln, Leonardtown, MD 20650
  • /61

    $440,000 Sold Jun 16, 2025

    • 2,379 Sq Ft
    • $185/SF
    • 46 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2022

    23445 Grovewood Ct, Leonardtown, MD 20650

    Welcome to 23445 Grovewood Court, an exquisitely maintained residence in the esteemed Clark's Rest community, where sophistication and serenity converge. This splendid 3-bedroom, 3.5-bath townhome offers an elevated living experience, combining impeccable design with unparalleled comfort. Step inside to discover an expansive and luminous open-concept floor plan, enhanced by refined finishes and

    John Gatton CENTURY 21 New Millennium

    23445 Grovewood Ct, Leonardtown, MD 20650
    • /55

      Est $592,677 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft

      41935 Green Hills Ln, Leonardtown, MD 20650

      41935 Green Hills Ln, Leonardtown, MD 20650
  • /54

    $635,000 Sold Jun 16, 2025

    • 2,692 Sq Ft
    • $236/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    20640 Laurel Ct, Leonardtown, MD 20650

    BEST AND FINAL OFFERS DUE BY MONDAY MAY 19th at NOON! Welcome to your own private retreat with a sparkling in-ground pool! This beautifully maintained 4-bedroom, 3.5-bath rambler is nestled on just under 3 serene acres in popular Chestnut Hills. With a sprawling main level and a massive 2,700+ sq ft unfinished walk-out basement, this home has the potential to offer over 5,500 total square

    Sarah Mulford-Martin EXP Realty, LLC

    20640 Laurel Ct, Leonardtown, MD 20650
    • /72

      Est $576,914 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,352 Sq Ft

      23638 Abraham Dr, Leonardtown, MD 20650

      23638 Abraham Dr, Leonardtown, MD 20650
  • /6

    $320,500 Sold Jun 13, 2025

    • 1,344 Sq Ft
    • $238/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1963

    44662 Blake Creek Rd, Leonardtown, MD 20650

    This cozy cottage is located in a beautiful, peaceful setting with over an acre of mature fruit trees and flowers. This solid home, with its good bones, awaits a refreshing touch, making it an ideal project for investors or enthusiastic DIY buyers looking to create their dream space. Offered as is, this cottage holds great potential to become a truly special retreat.

    Ruth Mudd RE/MAX One

    44662 Blake Creek Rd, Leonardtown, MD 20650
    • /37

      Est $393,475 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,656 Sq Ft

      39862 Big Pine Trail, Leonardtown, MD 20650

      39862 Big Pine Trail, Leonardtown, MD 20650
  • /76

    $460,000 Sold Jun 12, 2025

    • 2,524 Sq Ft
    • $182/SF
    • 61 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1969

    40827 Lake and Breton View Dr, Leonardtown, MD 20650

    Have you been searching for a home with the PERFECT Water Views!! Without; the Water view price??This home may be what your heart Desires!! Walk your kayaks right down the SAME block to the community beach access spot. The "walking beach" as they call it. This home has water views from BOTH levels. There are wood burning stoves on BOTH levels. The main beach access with playground and

    Connie Gunn CENTURY 21 New Millennium

    40827 Lake and Breton View Dr, Leonardtown, MD 20650
    • /27

      Est $588,621 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,100 Sq Ft

      23219 Jenifer Ct, Leonardtown, MD 20650

      23219 Jenifer Ct, Leonardtown, MD 20650
  • /51

    $415,000 Sold Jun 09, 2025

    • 1,348 Sq Ft
    • $308/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1994

    39880 Lady Baltimore Ave, Leonardtown, MD 20650

    Introducing this beautiful 3 Bedroom 2 Full Bath Rambler in Leonardtown. Some updates in this beautiful home include new vinyl flooring throughout, the Roof was replaced in 2019, the appliances are less than 2 years old, the Heat Pump was replaced in 2020, and much much more!This home features a huge pantry in the kitchen, a huge laundry room with even more cabinets for storage, a beautiful

    Matthew Burgan Infinitas Realty Group

    39880 Lady Baltimore Ave, Leonardtown, MD 20650
    • /34

      Est $318,681 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,252 Sq Ft

      22003 Point Lookout Rd, Leonardtown, MD 20650

      22003 Point Lookout Rd, Leonardtown, MD 20650
  • /41

    $572,000 Sold Jun 09, 2025

    • 3,272 Sq Ft
    • $175/SF
    • 2 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 2004

    23635 Abraham Dr, Leonardtown, MD 20650

    Welcome Home to Comfort, Charm, and SpaceThis stunning Colonial is nestled in a peaceful, sought-after community — the perfect retreat with 6 bedrooms and 4 full baths. Just minutes from downtown Leonardtown, you’ll have easy access to charming shops, popular restaurants, and scenic waterfront views at the Wharf.From the moment you enter, you’ll feel right at home. The warm and inviting

    Heather Hooper Berkshire Hathaway HomeServices PenFed Realty

    23635 Abraham Dr, Leonardtown, MD 20650
    • /37

      Est $499,878 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,715 Sq Ft

      41805 Meynard Ct, Leonardtown, MD 20650

      41805 Meynard Ct, Leonardtown, MD 20650
  • /25

    $447,000 Sold Jun 04, 2025

    • 1,504 Sq Ft
    • $297/SF
    • 48 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    21684 Potomac View Dr, Leonardtown, MD 20650

    3BR, 2Bath rancher with Front and Rear covered porches. Rear yard is ready for outdoor entertainment. Large side load garage with storage area over. Living Room with fireplace, dining area, open kitchen. No mandatory HOA, however the civic association is an optional fee.HVAC replaced a year ago.

    Terry Tenney Atlantic Southern Realty INC

    21684 Potomac View Dr, Leonardtown, MD 20650

Showing Results 241 - 280, Page 7 of 18

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