Leonardtown Real Estate

Leonardtown Real Estate

Welcome to Leonardtown, a charming town located in St. Mary's County, Maryland, USA. This historic town is known for its picturesque waterfront views, friendly community, and rich cultural heritage.

Leonardtown offers a perfect blend of small-town charm and modern amenities. With its quaint downtown area filled with local shops, restaurants, and art galleries, residents can enjoy a vibrant cultural scene right in their backyard. The town also hosts various events and festivals throughout the year, bringing the community together in celebration.

Nature enthusiasts will appreciate Leonardtown's proximity to outdoor recreational opportunities. From hiking and biking trails to water activities on the nearby Patuxent River, there is no shortage of ways to enjoy the great outdoors.

Families are drawn to Leonardtown for its top-rated schools and safe, family-friendly neighborhoods. The town's strong sense of community and excellent quality of life make it an ideal place to raise a family.

Whether you're looking to settle down in a peaceful waterfront town or seeking a close-knit community to call home, Leonardtown has something to offer everyone. Come explore all that this charming town has to offer and discover why Leonardtown is a hidden gem in St. Mary's County, Maryland.

Newest Listings in Leonardtown

$669,500
4 Beds ⋅ 4 Baths
This brick front colonial is nestled among the trees on a 4.5 acre lot 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 appliances. There are double ovens and a gas cooktop. There is also a sunny breakfast nook. There is a spacious screened porch off of the family room with a wrap-around deck (the perfect spot to enjoy the peaceful surroundings). The second level features four spacious bedrooms. The laundry area is also on this level. The master bedroom has a gas fireplace a large walk-in closet and large ceramic bath. The basement is finished with an office, book shelves, full bath and an entertaining area with a large wet bar.

40721 Merlin Way, Leonardtown

Listing courtesy of Leonard Realty, Inc.. Contact:

$589,900
4 Beds ⋅ 3 Baths
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 quartz countertops, a large upgraded island, custom backsplash, and a pyramid chimney hood that adds both style and function. You'll love the double ovens, 36” cooktop, and a spacious fridge—everything a modern cook needs. The home’s hidden gem is the butler’s pantry, complete with stylish navy cabinets, butcher block countertops, matching shelving, and a convenient beverage fridge—perfect for entertaining or additional kitchen storage. The primary bathroom is a spa-like retreat, featuring a large deluxe tiled shower with two shower heads, a built-in seat, ledge, and shelf for convenience, along with a beautiful freestanding tub to relax and unwind. Enjoy serene evenings on the 16x14 deck while watching the sunset over the flat backyard—ideal for outdoor fun or future landscaping projects. With extra windows added throughout, the home is flooded with natural light, creating a bright and airy atmosphere. Located in one of Leonardtown’s most desirable communities, The Meadows at Town Run, you're just a short distance from downtown Leonardtown, shopping, dining, and the highly rated Leonardtown schools. Don’t miss this fantastic opportunity to own a practically new home in a sought-after neighborhood! Schedule your showing today

43035 Bluejay Ln, Leonardtown

Listing courtesy of RE/MAX One. Contact: (443) 771-8009
$399,000
3 Beds ⋅ 3 Baths
DIAMOND IN THE ROUGH - HANDYMAN SPECIAL! SPEC’s: Ryan Modular Colonial Home, 2116 Sqft., 3 BR, 2.5 BA, Built in 1990; Original Owners, well maintained home; Brick wood burning stove in main den; Additional den/office space, finished attached garage w/separate outside entrance; Front Trex porch and back wood deck; Single car garage, 576 sqft. w/wood burning stove; AND, situated on over 9 Gorgeous wooded acres!!! The long private paved driveway leads you through a forest full of mature trees that opens up to an adorable colonial home with detached garage. This home has some cosmetic challenges but one can only imagine the endless possibilities you will have with this sturdy built home. Location is key with this colonial situated right off of Medley's Neck Road close to PAX, Webster Field, Fair Grounds, and the Leonardtown Downtown District. Seller has taken the time and the expense to have a pre-listing inspection and is still tackling all the major issues needing attention. This home is getting a new roof on the main house AND the detached oversized garage. The septic has been inspected and fully repaired. The well water has been tested and passed/certified, and the crawl space is set to be fully remediated and sealed by Home Services as well as the smaller attic space over the finished garage. St. Mary's County offers a huge property tax reduction for qualified homeowners owning over 5 acres such as Forest Retention and other agricultural opportunities. This property would easily hit the requirements allowing the owners save thousands a year in real estate taxes. I would highly recommend looking into these options: "agricultural use" tax reduction. SEE & verify with St. Mary’s County Zoning: https://dnr.maryland.gov/forests/Pages/programapps/fcmp.aspx This home is perfect for for the handyman with a vision and anyone who wants a more rural way of living!

20418 Scarlet Tanager Way, Leonardtown

Listing courtesy of RE/MAX 100. Contact:

$575,000
3 Beds ⋅ 3 Baths
This beautiful, one of a kind, contemporary style home has plenty of character and is awaiting its new owners. Prepare to be wowed upon entering the front door when you’re greeted by a massive great room to the left with gorgeous cathedral ceilings, a brick wood burning fireplace and an abundance of windows with natural lighting. To the right you’ll see the formal living room with a large bay window and window seat overlooking the front yard. Down the hallway, you’ll discover the magnificent kitchen complete with a center island, cook top, wall oven, and a brand new refrigerator and new dishwasher. You’ll love the ample amount of cabinets and the pantry for storage, as well as the open concept layout for cooking and dining. All 3 bedrooms can be found upstairs, including the incredible primary suite with an enormous walk in closet and primary bathroom that has double vanity sinks, a soaking tub and walk in shower. Complete with built in book shelves, a window seat, tall ceilings and recess lighting, this space is sure to impress! The primary bedroom also has a balcony overlooking the back yard, perfect for enjoying a cup of coffee in the morning and listening to the sounds of nature. Additional features include several original wooden pocket doors throughout the home, a central vacuum system, and an original (vintage) intercom/radio. Wait! There’s More! This home also has an attached two car garage with a work bench/ shelving and electric doors with remote access. Step outside and enjoy the amazing deck and gazebo, perfect for entertaining guests and relaxing. The back yard also has a wooden privacy fence, perfect for pets. This property sits on nearly 5 Acres in a highly sought after location in Leonardtown with no HOA. The large 12’ x 16’ lean-to shed conveys and is perfect for the storage of lawn equipment, toys and tools. This home has a brand new roof (2024) and the furnace was replaced approximately 4 years ago and has been maintained regularly, giving the new owner peace of mind for years to come. Make an appointment today and come see it before it’s gone! You don’t want to miss this one!

44403 Medleys Neck Rd, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: (301) 862-2169
$385,000
3 Beds ⋅ 4 Baths
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 flowing through the main level's open living and dining areas. A 3-sided, glass-enclosed wood-burning fireplace adds warmth and elegance to both spaces. The master suite features a stand-alone soaking tub, a spacious vanity, and a large separate shower. You'll love waking up to water views from your bed and relaxing in your bath with a scenic backdrop. The fully renovated lower level includes an additional bedroom and a full bathroom. This townhome has multiple outdoor living spaces, including an open sun deck and a covered patio on the lower level, which are ideal for entertaining or soaking in the tranquility of the water. Additional features include a one-car garage and a spacious storage and utility area.

40443 Breton View Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: (301) 862-2169
$385,000
3 Beds ⋅ 4 Baths
Why settle for a view of your neighbors when you can relax on your deck and take in the serene beauty of Cherry Cove in Breton Bay? This three-level townhome offers breathtaking water views and has been thoughtfully remodeled to blend modern style with comfort. Step inside to find a beautifully renovated kitchen featuring granite countertops, stainless steel appliances, and ample storage. The open layout is enhanced by hardwood floors that flow throughout the home, creating a warm and inviting atmosphere. A cozy two-sided fireplace adds charm and warmth, perfect for relaxing evenings. This home is ideal for comfortable living with three spacious bedrooms, two full baths, and two half bathrooms. Enjoy the convenience of a garage for your vehicles and extra storage. VA assumable loan is available!

40407 Breton View Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: (301) 862-2169
$759,900
5 Beds ⋅ 5 Baths
Here’s your chance to own a stunning, spacious and LESS THAN A YEAR OLD home in the highly sought after Clark’s Rest community in Leonardtown! Why wait for new construction when you can have this magnificent over 4000 sq ft home and be fully moved in & settled before the next school year?! This impressive home features 5 bedrooms (plus a large bonus room that could be used as a 6th bedroom), 4 full bathrooms & 1 half bath. Make your way up to the front door admiring the curb appeal with a spacious driveway and sidewalk leading you to your cozy front porch. Enter the front door to gleaming luxury vinyl plank flooring and an open 2-story foyer! Off the foyer you’ll find an office and formal dining room. The heart of the home is the STUNNING kitchen with all the bells and whistles boasting 42' cabinets, quartz counters, a large island with additional cabinetry and room for several barstools, additional sitting nook perfect for additional workspace or a mini fridge, stainless steel appliances (with a gas line available for future gas stove installation if preferred), and table space with a sliding glass door leading to your trex deck with steps down to patio...ideal for enjoying the peaceful backyard that backs up to woods! Upstairs, the large primary bedroom features a sitting area with a 2nd closet, large walk-in closet, and an attached bathroom with his & hers sinks, soaking tub, and separate shower. Upstairs also includes bedroom #2 with an en-suite full bathroom (also connected to the hallway) and an additional jack & jill bathroom shared by bedrooms #3 & #4. Bring the party to the finished basement with a spacious rec room with a sliding glass door… walkout level to back patio and backyard, bedroom #5, a full bathroom , an additional large room that could be used as 6th bedroom, and a large utility/storage room. HOA includes an array of amenities including an outdoor swimming pool, tennis court, basketball court, playground, clubhouse, and nature trail! This home is also conveniently located near the PAX River Naval base and just a 5 minute drive to downtown Leonardtown! Schedule your showing today!

23492 Watervale Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000
$489,900
6 Beds ⋅ 3 Baths

42522 Saint Margarets Dr, Leonardtown

Listing courtesy of The Southside Group Real Estate. Contact: 3019703636
$445,000
3 Beds ⋅ 4 Baths

41554 Briarwood Cir, Leonardtown

Listing courtesy of RE/MAX 100. Contact:

$724,900
5 Beds ⋅ 4 Baths
Spectacular best describes this beautiful home on a corner lot in the coveted Leonard's Grant neighborhood. On a wonderful corner lot that features a beautifully manicured lawn sits this 5 bedroom 3.5 bath home. Wander up the brick sidewalk to the front porch and through the front door to this meticulously maintained space. Beautiful engineered hardwood throughout the main level that features a large family room with gas fireplace, a kitchen with upgraded cabinets, countertops, and stainless steel appliances, a large walk in pantry, plus a formal dining and living space with french doors that could also be used as a home office. Upstairs you will find an expansive primary ensuite with double walk in closets and tiled bath with double sinks, soaking tub and QBHI signature walk in shower. Three additional bedrooms and a full bath plus laundry room are on this level. Lower level has large rec room with wet bar , 5th bedroom and 3rd full bath along with a large partially finished area that is currently used as a home gym. A screened porch, large brick patio, 2 car oversized garage and fenced yard round out this perfect package!

41504 Affirmed Way, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: (301) 862-2169
$740,000
5 Beds ⋅ 5 Baths

41408 W Citation St, Leonardtown

Listing courtesy of RE/MAX One. Contact: (443) 771-8009
$425,000
3 Beds ⋅ 2 Baths
This charming Cape Cod is brimming with character and ready for you to make it your own. A true gem sitting on 1.32 acres this home features a new roof, new HVAC, newer water heater, newer LVP flooring, fresh paint, cozy kitchen, plus a spacious family room that features a cozy wood-burning fireplace and beautiful exposed beams, perfect for creating warm memories. With a bedroom conveniently located on the main level and two generously-sized bedrooms upstairs, there’s room for everyone! Unfinished basement that has additional wood burning fireplace is ready for your finishing touches. Enjoy a large backyard complete with a large deck, ideal for relaxing or entertaining. Tucked away at the end of the cul-de-sac this lot provides peace and quiet without the hassle of through traffic. Just minutes from shopping and downtown Leonardtown this one is ready for new owners.

40781 Center 40 Cir, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: (301) 862-2169
Start Your Search