Leonardtown Real Estate

Leonardtown Real Estate

Welcome to Leonardtown, a charming and historic town located in Saint Mary's County, Maryland, USA. This quaint town is known for its rich history, beautiful waterfront views, and friendly community atmosphere.

Leonardtown offers the perfect blend of small-town charm and modern amenities. With its historic downtown area filled with unique shops, delicious restaurants, and cultural attractions, residents and visitors alike can enjoy a vibrant and bustling community.

Nature lovers will appreciate Leonardtown's proximity to the scenic Chesapeake Bay and the Patuxent River, providing plenty of opportunities for outdoor activities such as boating, fishing, and hiking. The town's picturesque parks and green spaces offer a peaceful retreat for those looking to relax and unwind.

In addition to its natural beauty, Leonardtown is also home to a thriving real estate market, with a variety of housing options to suit every lifestyle. Whether you're looking for a historic home with character or a modern waterfront property, Leonardtown has something for everyone.

Come experience the beauty and charm of Leonardtown, where small-town living meets modern convenience. Whether you're looking to buy a home or simply explore all that this town has to offer, Leonardtown is sure to capture your heart.

Newest Listings in Leonardtown

$425,000
3 Beds ⋅ 4 Baths
Gorgeous Townhomes "Compton" rear kitchen model. 2-Car Rear Load Garage, Open floor plan with Hardwood flooring, Stainless Steel Appliances, Granite Counters on the Island and Peninsula, Gas Cooking, Gas Heat, Tankless Water Gas Heater. Finished Rec/ room & Full bath in basement, Deck, Community Amenities feature: Clubhouse, Pool, Basketball & Tennis Courts, Playground. Just minutes from shopping, Boating, Fishing etc. PLEASE USE SHOE COVERS AT THE FRONT DOOR! Thanks

23399 Marview Ct, Leonardtown

Listing courtesy of HomeSmart. Contact: 4109522641
$549,900
5 Beds ⋅ 4 Baths
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 evenings in your rocking chairs. Step inside to a bright and airy entryway. To the left, you’ll find a formal living room, ideal for hosting guests, while the formal dining room on the right offers plenty of space for a full dining set. Continue down the hall to find a half bath, a large office/library filled with natural light, and the staircases leading to the upper and lower levels. The wide open floor plan at the back of the home features a cozy family room with a gas fireplace, perfect for snuggling up on your oversized sofa. The kitchen, complete with stainless steel appliances, wood floors, and 42" cabinets, boasts ample counter and cabinet space, a pantry, and a functional island with seating. The eat-in area comfortably accommodates casual family dinners and provides access to the patio. Step outside to enjoy the spacious, fully fenced backyard and a beautiful paver patio, perfect for adding a fire pit and hosting evening gatherings with friends and family. Upstairs, you’ll find four large bedrooms with generous closet space, along with a full hall bathroom and a primary bathroom. The expansive primary suite easily accommodates your furniture and includes a luxurious ensuite with dual vanities, a stand-up shower, and a garden soaking tub. The finished basement features newer carpet, a full bath, a sizable bedroom, a small rec area and an additional large recreation room perfect for movie nights, a bar, ping pong, or gym equipment. There’s also ample storage space in the utility room. The HVAC unit was updated in recent years. Located in Leonardtown, you’ll enjoy nearby amenities such as the Port of Leonardtown and The Square, offering excellent restaurants, bars, and shopping. Don’t wait—schedule your showing today, as this home won’t last long!

23585 Abraham Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: (443) 968-9595
$609,900
4 Beds ⋅ 3 Baths
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, center island, and plenty of countertop and cabinet space. There is a breakfast area off kitchen along with a large family room with cozy fireplace and sliding doors leading to the rear deck, overlooking the private back yard.. Also on this level is a full bath and the perfect private home office! Upper level has four large bedrooms, a shared full hall bath plus primary ensuite bedroom with WIC's and bath with large tiled walk in shower and soaking tub. Lower level is a walk out with rough in for full bath. This level is ready for your finishing touches and provides an addition 1700+ sq feet of living space, Outdoors has lots of room for gardening and walking trails along your wooded acreage. Private drive provides ample parking, along with a two car attached garage.

43610 Deer Run Ct, Leonardtown

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

$740,000
5 Beds ⋅ 5 Baths

41408 W Citation St, Leonardtown

Listing courtesy of RE/MAX One. Contact: (443) 771-8009
$594,000
2 Beds ⋅ 1 Baths
This dreamy waterfront getaway is the perfect spot for you to fully unwind and relax. Located directly along Breton Bay, you'll enjoy peace and serenity while only being a short 10 minute drive from downtown Leonardtown, or take a short boat ride across the bay to Fitzies for drinks and dinner. This charming cape cod offers amazing sunsets whether it's from the scenic deck, screened in porch or the private dock (with boat and jet ski lifts); the views can't be beat! The recently renovated home offers 2 bedrooms and 1 full bathroom, high speed internet, main level washer & dryer and an electric fireplace. The upstairs loft is perfect for an extra sleep area or rec room. Plenty of parking for you and your guests and multiple outbuildings including a detached shed to house all your lawn equipment, outdoor games, you name it! Your piece of happiness awaits!

40222 Breton Beach Rd, Leonardtown

Listing courtesy of Baldus Real Estate, Inc.. Contact:

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