Leonardtown Homes for Sale

Leonardtown Homes for Sale

Welcome to Leonardtown, Maryland – a charming town that beautifully blends rich history with modern living. Nestled in St. Mary’s County, Leonardtown is not only the county seat but also a vibrant community that showcases the best of Southern Maryland. With its picturesque streets, historic buildings, and friendly atmosphere, Leonardtown offers a unique lifestyle that appeals to families, retirees, and everyone in between.

One of the most captivating features of Leonardtown is its waterfront location along the scenic Leonardtown Creek. Residents and visitors alike can enjoy leisurely strolls along the boardwalk, savoring the breathtaking views and the gentle sounds of nature. The town is also home to a variety of local shops, restaurants, and cultural attractions, including art galleries and seasonal festivals that celebrate the community’s heritage.

For those looking to call Leonardtown home, there are a variety of homes for sale that cater to different tastes and budgets. From charming historic homes that echo the town’s storied past to modern new constructions that offer contemporary amenities, there’s something for everyone. The real estate market in Leonardtown is thriving, making it an ideal time to explore the available properties. Whether you’re searching for a cozy bungalow or a spacious family home, you’ll find a welcoming community that embraces both tradition and innovation.

Discover the charm of Leonardtown, where small-town warmth meets the conveniences of modern life. Your dream home awaits in this delightful corner of Maryland!

Newest Leonardtown Homes for Sale

5 Beds ⋅ 4 Baths

Welcome Home! A covered front entry and separate covered sitting porch create a charming first impression. Step inside to a two-story foyer with hardwood flooring and elegant moldings that continue into the dining room. To the left, a versatile room is ideal for a home office, library, study, or playroom. The dining room flows through the butler's pantry and adjoining walk-in pantry before opening to the kitchen. A large center island anchors the kitchen, featuring granite countertops, abundant cabinetry, a gas cooktop, and double wall ovens. The kitchen opens to the family room, where a gas fireplace creates a warm and inviting gathering space. Upstairs, the owner's suite features a spacious bedroom, two walk-in closets with custom closet systems, and a private bath with a double vanity, a soaking tub with a tile surround, and a beautifully tiled walk-in shower with dual shower heads. Three additional bedrooms, a full hall bath, and a conveniently located upper-level laundry room complete the upper level. The finished walk-out lower level is designed for entertaining, featuring a spacious recreation room with easy access to the patio and backyard. A fifth bedroom with a walk-in closet, currently outfitted as a fitness room, is complemented by a full bath, offering excellent flexibility for guests, multigenerational living, or a private retreat. An unfinished storage room provides valuable additional storage. As the day winds down, the composite deck offers a peaceful place to relax and enjoy the changing colors of the evening sky. The fully fenced backyard features raised garden beds and generous open space for outdoor enjoyment. Located in the sought-after community of Clark’s Rest, residents enjoy an exceptional lifestyle with amenities that include a pool, clubhouse, playgrounds, tennis courts, sidewalks, jogging trails, and more. Just minutes from downtown Leonardtown, shopping, dining, and the Leonardtown Wharf, this home offers the perfect blend of comfort, convenience, and community. Schedule your private tour today!

23214 Dairy Barn Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169

3 Beds ⋅ 2 Baths

If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for entertaining guests or creating lasting memories with family and friends. This move-in-ready home features a new HVAC system, beautifully updated bathrooms, brand-new flooring throughout, an encapsulated crawl space, and countless additional upgrades that offer both comfort and peace of mind. Opportunities like this don't come around often—schedule your showing today before it's gone!

18937 Hodges Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

3 Beds ⋅ 2 Baths

BEST AND FINAL OFFERS DUE BY MONDAY AUGUST 10th at 10:00 AM Owned by the same family since the 1960s, this 3-bedroom, 2-bath rambler has been lovingly maintained and is ready for its next chapter. This one already has the space, setting, and major improvements to make the possibilities exciting. The larger updates have already been taken care of, including a newer roof, siding, windows, new septic (early 2000's) and a 21x15 composite deck overlooking the backyard. The HVAC and furnace have also been serviced annually, allowing the next owner to focus on fresh paint, personal touches, and making the home their own. Inside, the oversized 25x12 owner’s suite includes a private bath and plenty of room for a king-size bed and sitting area. A spacious 35x12.5 addition with two separate entrances offers incredible flexibility for a family room, home office, playroom, guest space, in-law setup, studio, or hobby area. The layout also provides an opportunity to expand the kitchen and create an even larger gathering space. Original HARDWOOD flooring is under the carpet in all three bedrooms, just waiting to be uncovered and restored. Situated on a level, fully fenced lot just under half an acre, nearly every inch of the property is usable. There is plenty of room for pets, gardening, entertaining, outdoor play, or even a future pool. A storage shed and driveway parking for at least five vehicles add even more convenience. Two private community beaches with sweeping view of the Potomac River are just a short walk from the front door, and there is no HOA. Bring your fishing poles, beach chairs, and imagination. This one feels like home!

43927 Lanedon Dr, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

4 Beds ⋅ 4 Baths

Nestled in the serene community of Chestnut Hills of Leonardtown, this charming Colonial-style home offers a perfect blend of comfort and privacy. With 4 spacious bedrooms and 3.5 bathrooms, this residence spans an impressive 3,381 square feet, providing ample space for both relaxation and entertaining. Step inside to discover a warm and inviting interior. The open floor plan seamlessly connects the kitchen, dining area, and living spaces, making it ideal for gatherings. The kitchen is a chef's dream, complete with a butcher block island, modern appliances, generous cabinetry and plenty of counter space for meal prep. Crown moldings and chair rail add a touch of sophistication to the ambiance. The cozy family room, highlighted by a woodburning fireplace with glass doors and a mantel, creates a perfect spot for unwinding after a long winters day. The primary suite offers a very spacious private retreat with, large walk in closet and an en-suite bath, ensuring comfort and convenience. Venture outside to enjoy the expansive 2.89-acre lot, where nature surrounds you. The rear of the property boasts a beautiful retaining wall, a fire pit and backs up to Forest Retention Area providing a sense of continual privacy and tranquility. The outdoor space is perfect for entertaining or simply enjoying the peaceful views of the woods. Relax on the front porch, rear screened porch or deck, ideal for morning coffee or evening gatherings. The home also features a fully finished basement with both interior and outside entrances, offering additional living space, private gym area, private office, craft room or storage options. Create you own movie nights in the full theater room with projector and surround sound, which the equipment conveys. With an attached two-car garage and driveway, parking is a breeze. New roof and HVAC unit replaced in 2019. New water heater replaced in 2020. New insulated garage door 2026. Insulated crawl space and attic. French drainage system installed the home's perimeter. Additional features include a main floor laundry area and a security system for added peace of mind. As part of the Chestnut Hills community, residents have access to amenities, including rec field, basketball court, playground, and picnic areas, making it a wonderful place to call home. This property is not just a house; it’s a place where memories are made, and comfort is found. Experience the perfect blend of indoor and outdoor living in this delightful home.

20750 Deer Wood Park Dr, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

4 Beds ⋅ 2 Baths

Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2018, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers four well-appointed bedrooms, including a convenient entry-level bedroom, perfect for guests or those seeking single-level living. The primary suite features a walk-in closet and a spa-like bathroom complete with a soaking tub and a walk-in shower, providing a serene retreat at the end of the day. Additional interior highlights include plush carpeting, elegant hardwood floors, and ceiling fans that enhance comfort throughout the seasons. For those who appreciate technology, the home is equipped with a sound system, ensuring that your favorite tunes accompany you in every room. Outside, the property features a screened in porch, perfect for outdoor relaxation while enjoying the tranquility of your surroundings. The oversized detached garage offers ample space for vehicles and storage and has heat/ac, electricity and plumbing while complemented by a paved driveway for easy access. There is ample parking space for vehicles, campers, and more! Enjoy the peace of country living while being just a short drive from local amenities, shopping, and dining options. Don't miss the opportunity to make this beautiful residence your forever home!

25375 Loveville Rd, Leonardtown

Listing courtesy of RMG Realty. Contact: 5407091011

4 Beds ⋅ 2 Baths

Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished lower level expands the living space with an additional family room, two more bedrooms, and a second full bathroom—ideal for guests, a home office, or multi-generational living. With great bones and endless possibilities, this home is ready for your personal touches and updates. Fantastic location just minutes from shops, restaurants, schools, and waterfront amenities on Brenton Bay. Don't miss this rare opportunity to invest in one of Leonardtown's most desirable neighborhoods and create lasting value. Property is being sold strictly as-is. Schedule a showing today!

40743 Magee Dr, Leonardtown

Listing courtesy of Real of Pennsylvania. Contact: 8554500442

4 Beds ⋅ 3 Baths

Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area and into the kitchen. The kitchen was completely renovated in 2025 and features quartz counters, soft close cabinetry, tile floors, and stainless appliances. There's plenty of storage and counter space for easy meal prep and entertaining. For the grilling enthusiasts, a screened porch is a few steps away from the kitchen making it convenient for grilling and outdoor dining. As you progress down the hall, you're greeted with two spacious bedrooms, and a hall bathroom that was renovated in 2024 with a timeless design. At the end of the hall is the generous sized owners bedroom, complete with multiple closets, a dressing area, and an ensuite bathroom that was also renovated in 2024 with a sleek, modern motif. The owners suite features a private covered deck overlooking the back yard and farm land, making it a quiet retreat for relaxing after a long day. The lower level is partially finished with a 4th bedroom, 3rd full bathroom, and spacious second family room. The family room enjoys a bar for entertaining, as well as access to the two car garage. The remaining lower level contains laundry, built-in storage cabinets, and tons of storage space! The heat pump was replaced in 2024, and the roof was replaced with 40 year shingles in 2010. A Mini Fridge in the basement bar and a refrigerator in the garage convey. This home is uniquely located in Breton Bay, and enjoys views of the golf course, and views of the farmland behind the home. It's also within walking distance to the Breton Bay Clubhouse, and a mere 7 minutes to downtown Leonardtown. The community enjoys a beach area and playground for a minimal annual fee. Membership to the Breton Bay Country Club grants access to the pool and tennis courts. Welcome Home!

22010 Society Hill Rd, Leonardtown

Listing courtesy of Compass. Contact: (703) 229-8935

3 Beds ⋅ 3 Baths

Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft. Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the equally generous 37' x 8' rear porch, where you can relax and take in the peaceful waterfront scenery. Recent updates include new siding, a new roof, and a new gutter system. The side-load garage includes a staircase leading to a large upper-level storage area. Perfectly situated next to the neighborhood beach and pier, this property offers easy access to the waterfront and outdoor recreation. It's also within walking distance of the Breton Bay Golf & Country Club, where memberships are available for golf, swimming, and dining at the clubhouse restaurant. Whether you're looking for a year-round residence or a weekend retreat, this exceptional home combines stunning views, thoughtful updates, and an unbeatable location in one of Breton Bay's most desirable settings.

40579 Port Pl, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279

5 Beds ⋅ 4 Baths

Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so much more just inside the walls! Outside the walls of the home, features a shed, fenced in backyard, a beautifully manicured lawn watered by an in-ground irrigation system and several flower beds for all a plant enthusiast could ever ask for! Situated in the subdivision known as The Villages at Leonardtown, we are only minutes from all the shops, dining, and attractions Leonardtown has to offer, with a further drive to all the shops, attractions, dining near Pax River Naval Base and the surrounding area offers. Come take a look as this one won't last for long!

23620 Gunnell Dr, Leonardtown

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500

4 Beds ⋅ 4 Baths

Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the cul-de-sac. From the moment you arrive, you'll appreciate the welcoming community—where neighbors gather for evening walks, children ride bikes, and the sense of home extends well beyond the property lines. Inside, the updated kitchen serves as the heart of the home, featuring a large center island with a built-in beverage refrigerator, beautiful finishes, and durable tile flooring that flows into the bright, bumped-out breakfast area overlooking the backyard. Multiple living and entertaining spaces provide the flexibility today's buyers are looking for, whether hosting family gatherings or enjoying everyday life. Step outside to your private backyard retreat. The fully fenced, level yard offers plenty of room for children, pets, gardening, or outdoor games, while the expansive deck and covered patio beneath a pergola create the perfect spaces for entertaining or relaxing. A large storage shed provides additional room for lawn equipment, tools, and seasonal storage. Upstairs, the oversized primary suite is a true retreat, complete with a spacious walk-in closet featuring laundry hookups for added convenience. Three additional generously sized bedrooms, each with ample closet space, complete the upper level. The finished basement expands the home's versatility with a spacious recreation area, full bathroom, and a bonus room—ideal for a home office, fitness room, playroom, hobby space, or guest accommodations. An unfinished storage area ensures you'll have room for everything. Completing the home is a generously sized side-load two-car garage. Offering the space to grow, the updates buyers appreciate, and a location that's consistently in demand, 21395 Fairwood Ct. delivers the ideal combination of comfort, functionality, and community. If you've been searching for a home that offers room to spread out without sacrificing convenience, this Leonardtown property is one you won't want to miss.

21395 Fairwood Ct, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

3 Beds ⋅ 3 Baths

Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features hardwood flooring throughout most of the space, installed in 2019. The kitchen is appointed with cherry cathedral-style cabinetry, Corian countertops, an L-shaped center island, an Americast sink, and indirect lighting above and below the cabinets. The full suite of stainless-steel appliances includes a refrigerator with ice and water in the door, range, dishwasher, and built-in microwave. Hardwood stairs with white risers and balusters connect the home’s two levels. The foyer welcomes guests with 12-by-12-inch ceramic-marble tile and a fiberglass front door featuring sidelights and decorative leaded glass. The spacious primary bedroom includes a walk-in closet with a distinctive cedar ceiling. Its private bathroom offers a jetted soaking tub and separate shower. The second bedroom features luxury vinyl plank flooring, the third bedroom is carpeted, and the hall bathroom includes a tub-and-shower combination. Downstairs, the finished living area offers luxury vinyl plank flooring and a wood-burning fireplace surrounded by brick painted a stylish red. This level also includes a full bathroom with a tub-and-shower combination, a newer washer and dryer, and flexible space for relaxing, entertaining, working, or accommodating guests. The home is also wired for an alarm system. Outdoor living is a standout feature. A composite deck with vinyl pickets and handrails overlooks the fully fenced backyard, while the patio beneath the deck provides additional covered entertaining space. The backyard also includes a tiki-style entertainment area, a three-year-old 12-by-24-foot Intex above-ground pool, and a very large storage shed offering plenty of room for lawn equipment, tools, recreational gear, and seasonal items. Major improvements include the roof and hardwood flooring in 2019, HVAC in 2017, and water heater in 2015. Only two people have occupied the home since 2015, reflecting the light use and care it has received. With **NO HOA**, a level corner lot, an oversized garage, a blacktop driveway, abundant storage, extensive outdoor amenities, and a glimpse of the Potomac River, this home delivers the space and freedom to enjoy your property your way.

43954 Main Way Rd, Leonardtown

Listing courtesy of Keller Williams Flagship. Contact:

4 Beds ⋅ 3 Baths

Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes’ Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space. This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level is designed for everyday living with comfortable gathering spaces, an open flow, and room to make the home your own. Meadows at Town Run II is one of Leonardtown’s newest opportunities, with only 12 single-family homes planned in this section. Enjoy convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Planned amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Estimated delivery for early 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. This is one of only 12 single-family homes to be built in Meadows at Town Run II, making it a rare opportunity in one of Leonardtown’s most convenient communities. Enjoy close proximity to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers use QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about Homesite 5, available selections, incentives, and delivery timing. Photos may show a previously built Bell model or similar QBHI home and are for example purposes only. Actual home, features, finishes, options, and selections may vary.

42096 Wildflower Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009

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