6,717

Leonardtown, MD Homes

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    • /59

      Est $578,390 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,647 Sq Ft

      44403 Medleys Neck Rd, Leonardtown, MD 20650

      44403 Medleys Neck Rd, Leonardtown, MD 20650
  • /66

    $700,000 Sold Apr 25, 2025

    • 5,213 Sq Ft
    • $134/SF
    • 3 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 2015

    23267 Clarks Rest Rd, Leonardtown, MD 20650

    Welcome to this impressive and elegant 5-bedroom, 4 full and 2 half-bath home, offering the perfect blend of luxury, comfort, and energy efficiency. Located in a highly desirable community with walking sidewalks, a community center, playgrounds, and a sparkling pool, this property provides an exceptional lifestyle. Plus, it's only a convenient trolley ride away from downtown Leonardtown, where

    Chris Hill CENTURY 21 New Millennium

    23267 Clarks Rest Rd, Leonardtown, MD 20650
    • /26

      Est $286,883 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,243 Sq Ft

      22717 Point Lookout Rd, Leonardtown, MD 20650

      22717 Point Lookout Rd, Leonardtown, MD 20650
  • /64

    $739,900 Sold Apr 25, 2025

    • 6,015 Sq Ft
    • $123/SF
    • 179 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2013

    23749 Coventry Dr, Leonardtown, MD 20650

    This exceptional home is designed with luxury and space in mind, featuring expansive rooms thanks to bump-outs on two sides. The main level is an entertainer's dream, boasting an open floor plan that seamlessly connects the gourmet kitchen, breakfast room, family room, dining area, and sunroom. A library or office adds a touch of versatility. Hardwood floors run throughout the first two levels,

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    23749 Coventry Dr, Leonardtown, MD 20650
    • /54

      Est $556,972 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,608 Sq Ft

      42287 Bird Haven Dr, Leonardtown, MD 20650

      42287 Bird Haven Dr, Leonardtown, MD 20650
  • /4

    $645,000 Sold Apr 22, 2025

    • 3,400 Sq Ft
    • $190/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2010

    41443 Whimsical Ct, Leonardtown, MD 20650

    Welcome to this beautifully updated 5-bedroom, 3.5-bath Colonial home, offering the perfect blend of modern updates and classic charm. Step inside to find refinished hardwood floors, fresh paint, and new carpet throughout, creating a bright and inviting atmosphere.The heart of the home extends outdoors, where you'll discover a serene, tree-lined backyard with an incredible outdoor living

    Heather Foster RE/MAX One

    41443 Whimsical Ct, Leonardtown, MD 20650
    • /37

      Est $576,243 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,366 Sq Ft

      22266 Orchard Ct, Leonardtown, MD 20650

      22266 Orchard Ct, Leonardtown, MD 20650
  • /38

    $387,000 Sold Apr 21, 2025

    • 1,904 Sq Ft
    • $203/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1977

    22925 Downs Cir, Leonardtown, MD 20650

    Convenient, central location walkable to downtown Leonardtown! Tucked away on a quiet cul-de-sac, this house was beautifully renovated. ! Enjoy evenings on the generously oversized deck with pergola. Huge yard backs to trees. Great use of space throughout - master features walk-in closet and full master bath, finished basement offers lots of extra room!

    Ross Simone RE/MAX Realty Group

    22925 Downs Cir, Leonardtown, MD 20650
    • /49

      Est $598,373 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,602 Sq Ft

      42512 Dean Forest Way, Leonardtown, MD 20650

      42512 Dean Forest Way, Leonardtown, MD 20650
  • /117

    $725,000 Sold Apr 17, 2025

    • 5,862 Sq Ft
    • $124/SF
    • 19 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1997

    20503 Deer Wood Park Dr, Leonardtown, MD 20650

    Discover this expansive, custom-designed brick Colonial situated on 2 pristine acres in the highly sought-after Chestnut Hills subdivision. Meticulously maintained, this stunning home offers a grand 2-story foyer and a soaring family room with a cozy propane fireplace, all complemented by 9-foot ceilings throughout the main level.The open-concept kitchen is a chef’s dream, featuring a center

    Tracey Summers CENTURY 21 New Millennium

    20503 Deer Wood Park Dr, Leonardtown, MD 20650
    • /44

      Est $646,396 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 3,332 Sq Ft

      21871 Fairway Dr, Leonardtown, MD 20650

      21871 Fairway Dr, Leonardtown, MD 20650
  • /3

    $1,225,000 Sold Mar 31, 2025

    • 5,690 Sq Ft
    • $215/SF
    • 5 Beds
    • 6.5 Baths
    • Built 1984

    19710 Tower Hill Rd, Leonardtown, MD 20650

    Private 3.31 acre lot with beautiful views across the Potomac River. Home is almost 6000 square feet with close to 200 feet of rip rapped water frontage. 6 bedrooms and 5.5 baths including a private in law suite. Main level formal living room with doors leading to sunroom, formal dining room, private office with custom built ins, large family room off kitchen with wood burning fireplace and

    Jennifer Goddard CENTURY 21 New Millennium

    19710 Tower Hill Rd, Leonardtown, MD 20650
    • /12

      Est $345,437 Not Listed For Sale

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

      39834 Big Pine Trail, Leonardtown, MD 20650

      39834 Big Pine Trail, Leonardtown, MD 20650
  • /9

    $740,500 Sold Mar 27, 2025

    • 3,440 Sq Ft
    • $215/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2021

    43012 Bluejay Ln, Leonardtown, MD 20650

    Come visit this lovely Fairfax model home in the desirable community of The Meadows at Town Run. Built in 2021 by Quality Built Homes, this beauty will not disappoint. Nestled on a corner lot at the end of a quiet cul-de-sac and backing to trees add to the charm and privacy of this immaculately kept beauty. Inside the home you will find well thought-out appointments, to include 5 bedrooms and

    Robin Errington CENTURY 21 New Millennium

    43012 Bluejay Ln, Leonardtown, MD 20650
    • /99

      Est $627,682 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,680 Sq Ft

      21104 Rosebay Way, Leonardtown, MD 20650

      21104 Rosebay Way, Leonardtown, MD 20650
  • /56

    $1,450,000 Sold Mar 26, 2025

    • 3,709 Sq Ft
    • $391/SF
    • 4 Days On Market
    • 4 Beds
    • 7 Baths
    • Built 1983

    42297 Riverwinds Dr, Leonardtown, MD 20650

    Custom waterfront home on the Potomac River with breathtaking panoramic views. Designed for both family living and entertaining, this spacious residence boasts a thoughtfully remodeled gourmet kitchen by St. Maries Builders, a family room, sunroom, living room, and a large den with a full bath on the main level. Expansive windows maximize natural light and showcase stunning sunsets.The

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    42297 Riverwinds Dr, Leonardtown, MD 20650
    • /91

      Est $1,053,396 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 4,184 Sq Ft

      18878 Hodges Ln, Leonardtown, MD 20650

      18878 Hodges Ln, Leonardtown, MD 20650
  • /53

    $442,500 Sold Mar 25, 2025

    • 2,680 Sq Ft
    • $165/SF
    • 30 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1975

    22380 White Oak Rd, Leonardtown, MD 20650

    Welcome to your dream home in the highly sought-after Breton Bay community of Leonardtown, Maryland! This property is a true standout, with major repairs and thoughtful upgrades already done to provide ultimate comfort and peace of mind. At the top of the list are a brand-new septic system and a new roof, alongside a host of enhancements including a fenced rear yard, leaf guards, a new roof on

    Diana Washabaugh CENTURY 21 New Millennium

    22380 White Oak Rd, Leonardtown, MD 20650
    • /68

      Est $437,376 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,264 Sq Ft

      21764 Potomac View Dr, Leonardtown, MD 20650

      21764 Potomac View Dr, Leonardtown, MD 20650
  • /4

    $483,000 Sold Mar 24, 2025

    • 2,645 Sq Ft
    • $183/SF
    • 4 Beds
    • 3.5 Baths
    • Built 2019

    41482 Margrove Cir, Leonardtown, MD 20650

    This home is the perfect choice in Clarks Rest! It features the expansive Callaway floor plan and offers a beautiful pond view. This end-unit townhome includes a 2-car rear-load garage, gas heating, a tankless water heater, and gas cooking. With 4 bedrooms and 3.5 baths, you will enjoy granite countertops in the kitchen, stainless steel appliances, and upgraded cabinetry. The spacious living area

    Chris Norris JR. Topside Realty

    41482 Margrove Cir, Leonardtown, MD 20650
    • /42

      Est $334,349 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,584 Sq Ft

      23255 Hollywood Rd, Leonardtown, MD 20650

      23255 Hollywood Rd, Leonardtown, MD 20650
  • /23

    $285,000 Sold Mar 20, 2025

    • 1,669 Sq Ft
    • $171/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1966

    22239 Point Lookout Rd, Leonardtown, MD 20650

    Such a convenient location. Minutes from downtown Leonardtown, minutes from NAS Patuxent River. This property is has lots of space and a garage that offers so much. Relax on your front porch or back deck. High ceiling with skylights in super big family room. Primary bedroom exists to large rear deck. Garage has work space and air lines already in place. Oil heat keeps you warm on cold

    John Gatton CENTURY 21 New Millennium

    22239 Point Lookout Rd, Leonardtown, MD 20650
    • /95

      Est $587,312 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,264 Sq Ft

      40883 Meadow Dr, Leonardtown, MD 20650

      40883 Meadow Dr, Leonardtown, MD 20650
  • /41

    $449,900 Sold Mar 14, 2025

    • 1,488 Sq Ft
    • $302/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1981

    21717 Meadow Ct, Leonardtown, MD 20650

    Custom passive solar home designed for energy efficiency and comfort. This thoughtfully updated home features a newly remodeled kitchen with new cabinets, countertops, and appliances, plus LVT flooring throughout. The primary and half baths have been completely renovated.An open floor plan enhances natural light, with a solarium featuring a tiled floor. Additional highlights include a

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    21717 Meadow Ct, Leonardtown, MD 20650
    • /74

      Est $615,703 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,960 Sq Ft

      43225 Prince Pine Ct, Leonardtown, MD 20650

      43225 Prince Pine Ct, Leonardtown, MD 20650
  • /27

    $460,000 Sold Mar 14, 2025

    • 2,084 Sq Ft
    • $221/SF
    • 15 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2006

    41952 Loker Ct, Leonardtown, MD 20650

    Beautiful home in Academy Hills Neighborhood in Leonardtown! This home sits on the corner lot with a neighbor on one side and woods along the back. The location is convenient to town and Pax River but offers privacy and a quiet neighborhood without through traffic. The house features a living room, office, family room, eat in kitchen and dining room, laundry room, 4 spacious bedrooms, 2.5

    Diane Fenwick RE/MAX One

    41952 Loker Ct, Leonardtown, MD 20650
    • /40

      Est $515,462 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,404 Sq Ft

      20990 Woodmere Dr, Leonardtown, MD 20650

      20990 Woodmere Dr, Leonardtown, MD 20650
  • /95

    $605,000 Sold Mar 14, 2025

    • 3,120 Sq Ft
    • $194/SF
    • 42 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2011

    22395 Hood Ln, Leonardtown, MD 20650

    Over the creek and through the woods to your new house we go!! Welcome to ultimate privacy yet such an extremely convenient location. You are just minutes from shopping, restaurants, PAX Naval Base and more! Every time you travel back home it will feel like you are headed to a retreat! New full-length rear deck added in 2024- 900 finished square feet. New fencing in rear yard for pet

    Jessica Raley CENTURY 21 New Millennium

    22395 Hood Ln, Leonardtown, MD 20650
    • /30

      Est $469,131 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,628 Sq Ft

      40812 Spring House Ln, Leonardtown, MD 20650

      40812 Spring House Ln, Leonardtown, MD 20650
  • /90

    $961,000 Sold Mar 14, 2025

    • 4,416 Sq Ft
    • $218/SF
    • 14 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2022

    40095 Greentree Dr, Leonardtown, MD 20650

    BEST AND FINAL OFFERS DUE BY TUESDAY FEBRUARY 4th at 4:00 PM. Agents, please refer to agent remarks for offer instructions.Why wait for new construction? This like-new modern farmhouse is move-in ready and loaded with upgrades! Built by the highly requested Mednick Construction, this sale includes two lots totaling nearly 7 acres, offering ample space and privacy just outside downtown

    Sarah Mulford-Martin EXP Realty, LLC

    40095 Greentree Dr, Leonardtown, MD 20650
    • /41

      Est $503,359 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,861 Sq Ft

      41910 Nazareth Ct, Leonardtown, MD 20650

      41910 Nazareth Ct, Leonardtown, MD 20650
  • /36

    $875,000 Sold Mar 14, 2025

    • 3,150 Sq Ft
    • $278/SF
    • 3 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1961

    21790 Cove Ln, Leonardtown, MD 20650

    Welcome to your dream waterfront retreat on Cherry Cove Creek! This stunning 3-bedroom, 3-bathroom rambler sits on 2.79 picturesque acres in Leonardtown, offering over 3,150 square feet of thoughtfully designed living space. As the seller is in the process of moving, professional interior photos are on the way, but you don’t have to wait to explore the incredible features of this home.The

    Mark Frisco CENTURY 21 New Millennium

    21790 Cove Ln, Leonardtown, MD 20650
    • /54

      Est $463,126 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,016 Sq Ft

      44661 Deerfield Rd, Leonardtown, MD 20650

      44661 Deerfield Rd, Leonardtown, MD 20650
  • /27

    $375,000 Sold Mar 07, 2025

    • 1,456 Sq Ft
    • $258/SF
    • 53 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    22395 Gore St, Leonardtown, MD 20650

    Discover the charm of 22395 Gore St, nestled in the sought-after town of Leonardtown! This delightful home features a sunroom filled with natural light, offering the perfect space to relax or entertain year-round. The well-appointed kitchen boasts abundant storage, ideal for staying organized while inspiring your culinary creativity. Generously sized rooms provide endless flexibility for living,

    Billy Rabbitt The Southside Group Real Estate

    22395 Gore St, Leonardtown, MD 20650
    • /62

      Est $656,122 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,717 Sq Ft

      41585 Yoke Ct, Leonardtown, MD 20650

      41585 Yoke Ct, Leonardtown, MD 20650
  • /28

    $305,000 Sold Feb 28, 2025

    • 1,040 Sq Ft
    • $293/SF
    • 1 Day On Market
    • 3 Beds
    • 1 Bath
    • Built 1971

    40315 Wathen Rd, Leonardtown, MD 20650

    This recently renovated rambler features three spacious bedrooms and one modern bathroom. Set on a flat half-acre lot, the property offers ample outdoor space for recreation, gardening, or however you see fit. The new septic tank ensures efficient waste management, enhancing the home's overall functionality. With its updated interiors and generous lot size, this residence combines comfort and

    Brian Mayer Real Broker, LLC

    40315 Wathen Rd, Leonardtown, MD 20650
    • /55

      Est $568,881 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,332 Sq Ft

      42291 Bird Haven Dr, Leonardtown, MD 20650

      42291 Bird Haven Dr, Leonardtown, MD 20650
  • /2

    $430,000 Sold Feb 25, 2025

    • 2,402 Sq Ft
    • $179/SF
    • 3 Beds
    • 3.5 Baths
    • Built 2014

    23259 Lindsay Dr, Leonardtown, MD 20650

    Location location location!! The Beautiful Town of Leonardtown offers Trolley Car transportation for those nights at the local winery or pub for example. This Former model Townhome offers Upgrades and plenty of space for a growing family if needed. Bsmt recreation room can be used as a bedroom and has a full bath. Garage located off Rec Room has room for 2 cars if needed along with paved

    Diana Divver Real Broker, LLC

    23259 Lindsay Dr, Leonardtown, MD 20650
    • /25

      Est $517,692 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,398 Sq Ft

      43731 Stephenson Dr, Leonardtown, MD 20650

      43731 Stephenson Dr, Leonardtown, MD 20650
  • /109

    $655,000 Sold Feb 21, 2025

    • 2,469 Sq Ft
    • $265/SF
    • 110 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2002

    40721 Merlin Way, Leonardtown, MD 20650

    This 4.5 acre lot features "Wooded Privacy" for this attractive two story in the lovely community of Avenmar. An inviting foyer greets you at the front door with the formal dining room on the right and the living room on the left. The family room is straight ahead and is open to the kitchen. The kitchen features custom cabinets, a large island, granite counter tops and stainless steel

    Ron Leonard Leonard Realty, Inc.

    40721 Merlin Way, Leonardtown, MD 20650

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