6,686

Leonardtown, MD Homes

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  • /75

    $455,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,512 Sq Ft

    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
  • /37

    $510,000 Sold Dec 20, 2024

    • 2,764 Sq Ft
    • $185/SF
    • 2 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2005

    22540 Landing Way, Leonardtown, MD 20650

    Walk ability in Saint Marys Count how amazing! This home is right next to Leonardtown Wharf. Walk to the restaurants, festivals, and Santa sightings in Leonardtown. The beautiful home has 3 decks and 2 balconies. It has an elevator. Freshly professionally painted. New light fixtures. New Flooring. It has a newer roof.

    Trish Brow EXP Realty, LLC

    22540 Landing Way, Leonardtown, MD 20650
    • /61

      Est $719,218 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,876 Sq Ft

      22425 Archer St, Leonardtown, MD 20650

      22425 Archer St, Leonardtown, MD 20650
  • /17

    $3,800,000 Pending

    • Land
    • 52 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 New Millennium

    0 Cedar Lane Rd, Leonardtown, MD 20650
  • /64

    $625,000 Sold Dec 20, 2024

    • 1,144 Sq Ft
    • $546/SF
    • 21 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1961

    40481 Old Breton Beach Rd, Leonardtown, MD 20650

    Price included TWO Separate deeded LOTS! TWO PIERS!!! One New Sectic. This Dream Waterfront Home is being sold as a Turn-Key Home. Upgraded, Updated, new A/C and Ready for You. Did I mention TWO PIERS!!! The additional lot includes electric and septic, & utilities, as it previously had a home on it. The lot is being sold as is. Total acreage for both lots is 1.66. House = 1.32 acres and the lot

    Dawn Riley RE/MAX One

    40481 Old Breton Beach Rd, Leonardtown, MD 20650
    • /43

      Est $319,833 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 912 Sq Ft

      22373 Armstrong Dr, Leonardtown, MD 20650

      22373 Armstrong Dr, Leonardtown, MD 20650
  • /8

    $399,900 Coming Soon

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

    19137 Lake Dr, Leonardtown, MD 20650

    If moody modern colors, classy, and close to the water is your vibe, this is the one. Tucked just steps from the shores of the majestic Potomac River, this updated coastal retreat features 3 bedrooms, 2.5 baths, and two fireplaces...one stone fireplace in the cozy living room and another in the owner’s suite. Inside, the home has been freshly painted in a warm, modern palette with deep blues,

    Sarah Mulford-Martin EXP Realty, LLC

    19137 Lake Dr, Leonardtown, MD 20650
  • /56

    $450,000 Sold Dec 20, 2024

    • 2,226 Sq Ft
    • $202/SF
    • 81 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    40907 Cooper Dr, Leonardtown, MD 20650

    Nestled in one of the most sought-after neighborhoods, this charming residence offers an inviting blend of warmth, comfort and cozy. Boasting 3 bedrooms and 2.5 baths, this home is perfect for both families and those who love to entertain. New Roof just installed! The moment you step inside, you're greeted by beautiful hardwood floors that flow throughout the main living areas, enhancing the

    Barbara Blades CENTURY 21 New Millennium

    40907 Cooper Dr, Leonardtown, MD 20650
    • /58

      Est $418,616 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,286 Sq Ft

      40457 Breton View Dr, Leonardtown, MD 20650

      40457 Breton View Dr, Leonardtown, MD 20650
  • /2

    $529,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,328 Sq Ft

    22338 White Oak Rd, Leonardtown, MD 20650

    COMING SOON! Beautiful 4 bedroom, 2 1/2 bathroom colonial on over half an acre lot in Breton Bay! This home has has everything you could want with formal living & dining rooms, kitchen w/upgraded counter tops and appliances. The kitchen has bar style seating, a breakfast nook with built in bench and a seating area perfect for morning coffee and enjoying views of the back yard and pool. The

    Kelly Padgett CENTURY 21 New Millennium

    22338 White Oak Rd, Leonardtown, MD 20650
  • /25

    $279,000 Sold Dec 18, 2024

    • 1,056 Sq Ft
    • $264/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 2008

    41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650

    Experience the blend of comfort and convenience of the sought after "Foxwell Community" at this beautifully upgraded 2-bedroom, 1-bathroom condo located at 41800 Eastwick Lane #1303. With 1,056 square feet of living space, this one-owner home beams with pride of ownership. The interior features new hardwood flooring throughout and a full suite of new stainless steel appliances, complemented by an

    Kelly Niland Home Towne Real Estate

    41800 Eastwick Ln Unit 1303, Leonardtown, MD 20650
    • /26

      Est $447,787 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,414 Sq Ft

      42328 Saint Andrews Church Rd, Leonardtown, MD 20650

      42328 Saint Andrews Church Rd, Leonardtown, MD 20650
  • /2

    $525,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,935 Sq Ft

    22186 Monterey Place, Leonardtown, MD 20650

    Spacious brick rambler overlooking lake and golf course on full, walk-out basement with attached 2 car garage. Kitchen boasts brand new stainless appliances, pantry and lovely lake view! Lots of table space in the kitchen area or the formal dining area. Both family room and rec room have wood burning fireplaces. This Mid-century/Modern open floorplan is a delight! Cozy family room off of kitchen,

    Barbara Stellway KW Metro Center

    22186 Monterey Place, Leonardtown, MD 20650
  • /52

    $549,900 Sold Dec 17, 2024

    • 4,832 Sq Ft
    • $114/SF
    • 14 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2004

    23585 Abraham Dr, Leonardtown, MD 20650

    IMMACULATE! Beautiful 5-bedroom, 3.5-bath 4832 SQFT Colonial with a 2-car garage is ready to welcome you!As you arrive, the lovely landscaping and inviting front elevation immediately catch your eye. The architectural roof is just a few years old, and the fully fenced backyard sits on a generous 0.38-acre lot in Leonardtown.The charming front porch is perfect for enjoying quiet

    Mark Frisco CENTURY 21 New Millennium

    23585 Abraham Dr, Leonardtown, MD 20650
    • /47

      Est $595,419 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,929 Sq Ft

      23577 Abraham Dr, Leonardtown, MD 20650

      23577 Abraham Dr, Leonardtown, MD 20650
  • /26

    $249,900 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,212 Sq Ft

    21749 Point Lookout Rd, Leonardtown, MD 20650

    Charming Mid-Century Rambler Near St. Mary’s LakeStep into classic mid-century style with this well-maintained rambler, offering timeless charm and solid construction. Featuring hardwood floors throughout, this home boasts larger-than-average bedrooms for its era—providing extra comfort and space rarely found in similar homes.Enjoy morning coffee on the welcoming front porch and take advantage of

    John Gatton CENTURY 21 New Millennium

    21749 Point Lookout Rd, Leonardtown, MD 20650
  • /31

    $589,000 Sold Dec 13, 2024

    • 3,439 Sq Ft
    • $171/SF
    • 69 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2001

    41470 Garrett Ct, Leonardtown, MD 20650

    This spacious Cape Cod, nestled at the end of a quiet cul-de-sac, offers the perfect blend of privacy and convenience. Boasting over 3,400 square feet of living space, this home features 4 generous bedrooms and 3 full bathrooms. Two main floor primary bedrooms! Enjoy the serene views as this property as it backs to trees on both the rear and side, providing a tranquil setting with no HOA.

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    41470 Garrett Ct, Leonardtown, MD 20650
    • /77

      Est $478,408 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,275 Sq Ft

      22909 Cedar Lane Rd, Leonardtown, MD 20650

      22909 Cedar Lane Rd, Leonardtown, MD 20650
  • /64

    $1,100,000 Under Contract

    • 5 Beds
    • 5.5 Baths
    • 6,508 Sq Ft

    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 safety and

    Helen Wernecke Berkshire Hathaway HomeServices PenFed Realty

    23350 Potato Hill Farm Ln, Leonardtown, MD 20650
  • /18

    $385,000 Sold Dec 11, 2024

    • 2,604 Sq Ft
    • $148/SF
    • 36 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1994

    40443 Breton View Dr, Leonardtown, MD 20650

    Why settle for a typical subdivision when you can enjoy the beauty and lifestyle of Breton Bay? With its proximity to Breton Bay Country Club—offering pool, tennis, and golf amenities—and historic Leonardtown for dining, shopping, and events, this townhome is the perfect blend of convenience and coastal living. The 3-level, three-bedroom, 3.5 bath townhome features beautiful luxury vinyl plank

    Anne Davis CENTURY 21 New Millennium

    40443 Breton View Dr, Leonardtown, MD 20650
    • /86

      Est $411,029 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 2,676 Sq Ft

      40427 Breton View Dr, Leonardtown, MD 20650

      40427 Breton View Dr, Leonardtown, MD 20650
  • /43

    $700,000 Under Contract

    • 5 Beds
    • 4 Baths
    • 3,153 Sq Ft

    21549 Point Lookout Rd, Leonardtown, MD 20650

    Contemporary Farmhouse Living on over 24 acres! Drive down the lane past some of your pasture acreage on the left to your 3,000+ sf home backing to mature trees and wooded trails. A small pond is also located on the property. Possibilities abound with the level acreage in front! The property is located between Leonardtown and Callaway close to the Saint Mary's Rive State Park area. Close to

    MaryAnne Crewse O'Brien Realty ERA Powered

    21549 Point Lookout Rd, Leonardtown, MD 20650
  • /4

    $75,000 Sold Dec 09, 2024

    • Land
    • 1.16 Acres
    • $64,655 per Acre
    • 482 Days On Market

    40435 Old Breton Beach Rd, Leonardtown, MD 20650

    IMPROVED PRICE!!!!! Motivated seller, bring your offer!!!!!!Spectacular views of the Potomac River! Recreational waterfront property for sale. Lots included in price are: 500-34, 33 and 32. Parcel 263 across the road also conveys. This property is listed for recreational use, it is non-buildable. There was a dock at one time and it is likely a new one can be built.

    Kelly Loveless Berkshire Hathaway HomeServices PenFed Realty

    40435 Old Breton Beach Rd, Leonardtown, MD 20650
    • /9

      Est $513,235 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,149 Sq Ft

      20995 Chestnut Ridge Dr, Leonardtown, MD 20650

      20995 Chestnut Ridge Dr, Leonardtown, MD 20650
  • /120

    $843,000 Under Contract

    • 5 Beds
    • 4 Baths
    • 4,648 Sq Ft

    40738 Bobwhite Ln, Leonardtown, MD 20650

    Welcome to this extraordinary 5,242 sq. ft. estate, perfectly nestled on 3.52 acres of beautifully landscaped grounds in the prestigious Avenmar community. Privately situated at the end of a tranquil cul-de-sac, this five-bedroom, four-bathroom home is a masterclass in luxury, craftsmanship, and timeless design.From the moment you arrive, the expansive private driveway and lush, mature

    Jessica Raley CENTURY 21 New Millennium

    40738 Bobwhite Ln, Leonardtown, MD 20650
  • /45

    $365,000 Sold Dec 06, 2024

    • 1,956 Sq Ft
    • $187/SF
    • 3 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1980

    21726 Lake Cir, Leonardtown, MD 20650

    MULTIPLE OFFERS RECEIVED - OFFER DEADLINE 11/14 4PM Looking for an affordable home in a great location? This split foyer in Breton Bay is calling your name! This property is perfect for those looking to put their own touch on their home and offers tons of space with 4 bedrooms and 3 full bathrooms as well as a bonus room downstairs that could be used as an extra bedroom, playroom, storage

    Amanda Littleford Infinitas Realty Group

    21726 Lake Cir, Leonardtown, MD 20650
    • /81

      Est $762,203 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,000 Sq Ft

      43164 Gum Spring Dr, Leonardtown, MD 20650

      43164 Gum Spring Dr, Leonardtown, MD 20650
  • /82

    $574,000 Under Contract

    • 5 Beds
    • 2.5 Baths
    • 3,238 Sq Ft

    23075 Hollywood Rd, Leonardtown, MD 20650

    Seller offering up to 3% in Closing assistance - Close in July, just in time for summer in Leonardtown! Built in 1942, this 5-bedroom, 2.5-bath home offers over 3,200 square feet of character-filled living space Original hardwood floors, arched openings, detailed trim work, and vintage glass door knobs are just a few of the timeless details that give this home its warmth and soul—while updates

    Katy Galloway CENTURY 21 New Millennium

    23075 Hollywood Rd, Leonardtown, MD 20650
  • /87

    $625,000 Sold Dec 06, 2024

    • 2,980 Sq Ft
    • $210/SF
    • 4 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1997

    43610 Deer Run Ct, Leonardtown, MD 20650

    Wonderful brick front colonial home sitting on over 6.5 acres in Chestnut Hills. This home has been recently updated with fresh paint, new carpet, beautiful solid surface countertops and tiled backsplash along with refreshed baths and is ready for its new owners to call home. Main level has formal living and dining areas with hardwood floors, a generously sized kitchen with SS appliances,

    Jennifer Goddard CENTURY 21 New Millennium

    43610 Deer Run Ct, Leonardtown, MD 20650
    • /56

      Est $710,772 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,524 Sq Ft

      40688 Clearfields Ct, Leonardtown, MD 20650

      40688 Clearfields Ct, Leonardtown, MD 20650
  • /43

    $449,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,820 Sq Ft

    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 down by the fire

    Rob Schou EXP Realty, LLC

    40905 Knight Rd, Leonardtown, MD 20650
  • /30

    $445,000 Sold Dec 06, 2024

    • 1,836 Sq Ft
    • $242/SF
    • 115 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1991

    22135 Cartwright Rd, Leonardtown, MD 20650

    New & Updated!! New Roof and Gutters!! Bring your ideas and discover the allure of this custom-built gem situated in a serene locale of Leonardtown, a stone's throw from the vibrant St. Mary's fairgrounds and the bustling heart of the community. This distinguished home spans 1,836 square feet, offering 3 bedrooms, 2 full bathrooms, and a convenient half bath. The residence is a testament to

    adrian abramson The Southside Group Real Estate

    22135 Cartwright Rd, Leonardtown, MD 20650
    • /80

      Est $589,057 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,916 Sq Ft

      23598 Abraham Dr, Leonardtown, MD 20650

      23598 Abraham Dr, Leonardtown, MD 20650
  • /85

    $695,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 4,019 Sq Ft

    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 Leonardtown just 5

    Laura Bernth RE/MAX One

    23055 Town Run Dr, Leonardtown, MD 20650
  • /81

    $620,000 Sold Dec 05, 2024

    • 2,614 Sq Ft
    • $237/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2021

    43035 Bluejay Ln, Leonardtown, MD 20650

    Welcome to this beautiful 4-bedroom, 2.5 bath Montross Model, built by Quality Built Homes, Inc. in 2021, offering over 2,600 sq ft of luxurious living space that shows like new! This meticulously maintained home features luxury vinyl plank (LVP) flooring throughout, with upgraded tile in the bathrooms—there’s no carpet anywhere in the house!The chef's kitchen is a masterpiece, showcasing

    Laura Bernth RE/MAX One

    43035 Bluejay Ln, Leonardtown, MD 20650
    • /68

      Est $1,015,681 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 6,226 Sq Ft

      40741 Merlin Way, Leonardtown, MD 20650

      40741 Merlin Way, Leonardtown, MD 20650
  • /7

    $772,000 Under Contract

    • 4 Beds
    • 4.5 Baths
    • 3,000 Sq Ft

    44798 Medleys Neck Rd, Leonardtown, MD 20650

    Other lots in the area, call us to discussTBB - Custom Home - Many other floor plans and locations - call to discuss

    Marie Jozwik RE/MAX Realty Group

    44798 Medleys Neck Rd, Leonardtown, MD 20650
  • /49

    $708,750 Sold Dec 05, 2024

    • 4,984 Sq Ft
    • $142/SF
    • 56 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2002

    22876 White Swan Way, Leonardtown, MD 20650

    Welcome to your new home in the Avenmar neighborhood of Breton Bay where there is something for everyone, including your fur babies! This amazing QBH Willow model boasts a beautiful brick front Colonial with a sideload 2 car garage that sits on 3.6 acres off of a private road at the end of a cul de sac. The first floor has hardwood and ceramic tile flooring, featuring a bedroom and full bathroom.

    Ross Simone RE/MAX Realty Group

    22876 White Swan Way, Leonardtown, MD 20650
    • /54

      Est $576,379 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,982 Sq Ft

      23285 Jenifer Ct, Leonardtown, MD 20650

      23285 Jenifer Ct, Leonardtown, MD 20650
  • /2

    $1,740,000 Under Contract

    • Land
    • 3.85 Acres
    • $451,948 per Acre

    25845 Point Lookout Rd, Leonardtown, MD 20650

    This listing is 3.85 acres of a total 6-acre commercial property in Leonardtown, Maryland. Don't miss the chance to invest in this thriving and picturesque community. Whether you're looking to create a retail haven, upscale office space, or a dining destination, this property has all the ingredients for success. With its size and location near Patuxent Naval Air Station, this property is a blank

    Anne Davis CENTURY 21 Commercial New Millennium

    25845 Point Lookout Rd, Leonardtown, MD 20650

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