Leonardtown MD Real Estate & Homes for Sale

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Beds:
5
Baths:
4.00
Sq.Ft.:
4,340
Status:
NEW LISTING
MLS#:
MDSM2030894
Type:
Single Family-Detached
Subdivision:
Kingston Estates
Lot size:
0.73 Acres
Year built:
2004
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

PROFESSIONAL PICTURES COMING NEXT WEEK! Welcome to 42032 Starlight Drive in Leonardtown, MD, a spacious and beautifully updated home offering comfort, flexibility, and thoughtful upgrades throughout. This beautiful property backs to woods, providing a peaceful and private setting to enjoy year-round. Inside, fresh new paint throughout, new carpet upstairs, and new vinyl plank flooring in the basement give the home a clean, move-in-ready feel. The main level features generous living spaces, including a large office with glass French doors, perfect for working from home, studying, or creating a quiet flex space. The living room is warm and inviting with a new propane fireplace, accented by a striking floor-to-ceiling brick backdrop and mantle. The gourmet kitchen offers stainless steel appliances, abundant cabinet space, and a large pantry, making it ideal for everyday cooking and entertaining. Upstairs, you’ll find comfortable bedrooms and refreshed finishes, while the lower level adds incredible versatility. The basement includes another potential bedroom, a full kitchen, a full bath, and a stackable washer and dryer that convey, making it an excellent option for an in-law suite, guest space, or potential income-producing area. There is also plenty of storage throughout the home, giving you room for everything. Outdoor living is a major highlight, with a maintenance-free deck featuring storage underneath, plus a professionally installed paver patio with firepit—perfect for relaxing evenings or entertaining guests while enjoying the wooded backdrop. The driveway provides extra parking alongside the garage, adding everyday convenience. Additional valuable features include a newer roof, dual-zone HVAC with units replaced in 2010 and 2021, an emergency backup generator, and a fully paid-for solar system with warranty, offering peace of mind and energy efficiency. This home combines space, updates, privacy, flexibility, and long-term value in a desirable Leonardtown location.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,500
Status:
NEW LISTING
MLS#:
MDSM2031120
Type:
Single Family-Detached
Subdivision:
Little St Annes
Lot size:
2.29 Acres
Year built:
2003
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Country Living at it's best!!! NO HOA in a minor subdivision of only 7 houses within a couples of miles of downtown Leonardtown. Two primary suites or one in-law ADA approved apartment on main level, includes gas fireplace in living area, pocket doors, walk in shower, coffee bar with small refrigerator, three season porch and direct access to laundry facilities/garage w/ADA approved ramp. Year round heated sunroom. Oh by the way, insulated inside walls with six inch exterior walls. Main house upgraded kitchen, built in refrigerator, eat at counter with bar stools. Granite counter tops. Butler's pantry w/wine refrigerator. Recessed lights through out, Cali Bamboo flooring. Dining room and a study with built in desk and ample storage. Upstairs second primary suite, walk-in closet, tub with shower. Additional two bedrooms feature a Jack and Jill bath. Take a walk on the deck walkway to the Pavilion and enjoy the view of the 20 plus raised bed garden of vegetables or walk over to the chicken coup and have fresh eggs for breakfast. Summer and fall will treat you to the many eatible fruit, fig and berry bushes and trees that enhance the landscaping of this private 2.29 acre lot. Many additional features like a small fenced area for pets, garden shed, second refrigerator, upright freezer, utility sink, extra cabinets, custom drapes, French doors, extra large TV, propane free standing stove, 9 foot ceilings, to mention a few. Detailed list and manuals will be provided.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,014
Status:
NEW LISTING
MLS#:
MDSM2031122
Type:
Single Family-Detached
Subdivision:
Breton Bay Landing
Lot size:
0.42 Acres
Year built:
1990
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Built as a model for the neighborhood, this 3-bedroom, 2-bath Rambler will have you checking off your search boxes! Located on a quiet-cul-de-sac street in desirable Breton Bay, this lovely home includes more than 3,000 sq ft of living space and plenty of storage, too. Attractive landscaping greets you on your way to the welcoming front porch. A custom-glass front door leads into a spacious foyer, and main floor that features solid Oak hardwood flooring. New windows flood the the roomy formal living room with natural light, and the space centers on the warm hearth & wood-burning fireplace. Serve guests in the formal dining room, or head to the open kitchen/family room for more informal gatherings. Soft-close-Oak cabinets and drawers, Granite counters, wine rack, pull-out shelves, an island w/ breakfast bar, and NEW refrigerator make this kitchen any cook's delight! When the temp is right, head out the back door and enjoy meals on the screened porch. The flat yard backs up to trees, and is perfect for fun & games with plenty of room to play! Let Fido play, too, as the property is surrounded by an invisible fence. Three spacious bedrooms on the main floor make one-level living easy. The Primary suite includes double walk-in closets, and an updated bath with warm Cork flooring, soaking tub and tiled shower. An updated hall bath w/ tiled tub & shower, and convenient laundry/mud room complete the main floor. Head down to the lower level, and envision how you will use the large rec room! Natural light from two large windows shines on a space that can fit game tables, big screen TVS w/ seating, fitness equipment, or all three! An additional bonus room makes for a quiet retreat, a great home office, or gamer/media room. Unfinished space allows for all your storage needs. A 2-car garage keeps the cars clean, and a backyard shed helps keep it tidy. There are generator & RV hookups, and for added peace-of-mind, the HVAC system & water heater are 5-years young! The Breton Bay community features a waterfront park with beach, fishing/crabbing dock, picnic areas and playground. A public 18-hole golf course w/clubhouse offers memberships that include tennis and pool. Great amenities, Leonardtown schools, near shopping, restaurants, and main commuter routes... this home is one that you will not want to miss. Request a showing today!

Beds:
5
Baths:
3.00
Sq.Ft.:
3,464
Status:
NEW LISTING
MLS#:
MDSM2030444
Type:
Single Family-Detached
Subdivision:
Breton Bay Estates
Lot size:
0.4 Acres
Year built:
1978
Courtesy: Berkshire Hathaway HomeServices PenFed Realty 410-394-0990
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ADDITIONAL INFORMATION

Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven rental history that is hard to find. The secondary residence isn't just a suite; it’s a high-demand 2-bedroom, 1-bath apartment with a private exterior entrance, full kitchen, dedicated laundry, and its own private deck. With a track record of long-term stability—including a previous seven-year tenancy—this space provides immediate income potential in a high-demand area. The main residence is a contemporary styled home featuring vaulted ceilings, hardwoods, and a light-filled open concept. The cottage kitchen boasts custom cabinetry, a rolling island, and a storage closet this seller used as wine storage. The entire top level serves as a private owner’s sanctuary with an ensuite bath and walk-in closet, while two additional spacious bedrooms occupy their own dedicated level for maximum privacy. This home boasts a brand-new septic system installed in the Fall 2025, fresh paint throughout, and new carpet in both the home and the apartment. If it is not a rental income you are seeking, reimagine this home into two distinct living experiences under one roof—perfect for multigenerational families, a premium home office suite, or a high-end guest wing. Living in a waterfront community with a beach, pier, playground, and optional golf club membership. This can be more than a home; it may be a strategic financial move to allow the rental income to offset your mortgage. Let this property work for you!

Beds:
5
Baths:
5.00
Sq.Ft.:
2,756
Status:
Active
MLS#:
MDSM2031020
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.36 Acres
Year built:
2007
Courtesy: Residential Plus Real Estate Services 301-934-9985
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ADDITIONAL INFORMATION

This 5 BR, 3 full BA, 2 half BA home offers nearly 3,000 square feet of comfortable living, but what truly sets it apart is everything beyond the main house. Step outside to your own backyard oasis featuring an in-ground saltwater pool, gazebo, and expansive entertaining space—perfect for summer gatherings or quiet evenings under the stars. Need room to grow, work, or host? The 28x40 detached garage with finished upper-level suite opens the door to endless possibilities—ideal for multi-generational living, guest quarters, home office, or aturn into a recreation room w/wet bar. Set on 1.36 acres, this property offers the privacy and freedom you’ve been looking for, with space for hobbies, storage, or simply enjoying the outdoors—without the restrictions of an HOA. Located just minutes from Leonardtown and an easy commute to Naval Air Station Patuxent River, this home delivers the perfect balance of convenience and seclusion. If you’ve been searching for a property that offers more than just a house—something with versatility, function, and lifestyle built in—this is it.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,554
Status:
Active
MLS#:
MDSM2031006
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

****Mid May Delivery*** Homesite # 136 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, brushed nickel fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard—perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds—all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,507
Status:
Active
MLS#:
MDSM2030988
Type:
Single Family-Detached
Subdivision:
Breton Bay Estates
Lot size:
0.58 Acres
Year built:
1974
Courtesy: KW Metro Center 703-535-3610
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ADDITIONAL INFORMATION

Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-bedroom, 3-bath split foyer offers space and comfort, and is move-in ready! The main level showcases stunning hardwood floors and a bright, inviting layout perfect for everyday living. The fully finished walk-out lower level features a spacious family room with a cozy fireplace, creating the ideal space for relaxing or entertaining. A large mudroom and laundry area provides excellent functionality and storage. Mudroom has epoxy flooring, laundry sink and oversized washer; washer & dryer are 1 year old. Kitchen & all 3 baths have tiled flooring. Set on a private half-acre lot, the home also offers a rear deck, two-car garage, and generous storage throughout. Leaf Filter brand gutter guards have transferable warranty. Residents enjoy optional membership to the Breton Bay Golf Course, pool, and tennis facilities, along with access to the community beach park and pier—making it easy to embrace the best of Southern Maryland living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,636
Status:
Active
MLS#:
MDSM2030794
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.46 Acres
Year built:
1927
Courtesy: Franzen Realtors, Inc. 301-862-2222
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ADDITIONAL INFORMATION

Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still exhibiting original craftmanship and renovations throughout the years. Livable preserved charm but perfect for an updating to make it your own. Roomy kitchen opens to great room with 9 ft. beamed ceilings, bay window, and a brick fireplace with woodstove all open to expansive sunroom. Master bedroom with large bath with soaking tub, 6’ x 9’ walk in closet and even a bidet. Entrance foyer with laundry area. Second floor 15’ x 7’ loft perfect for extra sleep or rec room. Over 1,600 sq. ft. of finished area plus a newly constructed detached 480 sq. ft. 2 car garage with 2nd level partly finished coach house apartment and 6’ x 10’ covered porch with waterfront views. Apartment is under roof, sided with electrical and plumbing rough-in with over 400 sq. ft. Fully permitted (that’s important). Combined square footage when completed will be over 2,000. Coach House perfect for guests, family, or rental income. Over 100 feet of protected shoreline with 80 ft. pier plus 10’ x 20’ L platform, power boat lift and 1 slip. Nice sized 10 ‘x 21’ deck accessing pier on shoreline. Wooded lot at the end of a dead-end street!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,604
Status:
Active
MLS#:
MDSM2030032
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

***Mid-May Delivery*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft 4 Bedrooms 3.5 Baths 1-Car Garage Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a main-level entry that opens into a finished rec room or 4th bedroom with a full bath, perfect for a guest suite or home office. Upstairs, enjoy 9’ ceilings, luxury vinyl plank flooring, and an open-concept kitchen featuring 42" upgraded maple cabinets, upgraded granite countertops, a large center island, walk-in pantry, and stainless steel GE appliances. The kitchen flows seamlessly into the dining area and oversized family room, with access to a 14x12 maintenance-free deck overlooking your private, fenced-in backyard. The upper level boasts a spacious owner’s suite with tray ceiling, walk-in closet, and a luxurious ensuite bath with dual vanities and QBHI’s signature deluxe tiled shower. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the top floor. Additional features include: Oversized 1-car garage and 2-car wide driveway, finished and painted garage with drywall, smart home technology with IQ Pro command center, Skybell camera doorbell, and smart thermostat Low-maintenance exterior with stone-to-grade front (per elevation), sodded yard, vinyl fencing, and landscaping package. Community amenities include sidewalks, recreation center, pool, playground, pickleball, and tennis courts, all in the heart of charming Leonardtown. Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,854
Status:
Active
MLS#:
MDSM2030476
Type:
Single Family-Detached
Subdivision:
Meadows At Town Run
Lot size:
0.21 Acres
Year built:
2022
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome home to 23073 Town Run Drive! Built in 2022, this beautifully maintained home in the highly sought-after neighborhood of The Meadows at Town Run in Leonardtown is truly a standout. Built by QBH, this desirable Ashland model offers thoughtfully designed living space with an open and inviting floor plan—perfect for both everyday living and entertaining. This home truly shines, showing like a designer model home with stunning custom finishes and upgrades throughout. This spacious residence features 3 generously sized bedrooms, 2 full bathrooms, and a 2-car front-load garage. From the moment you enter, you’ll appreciate the attention to detail, including elegant crown molding, chair rail accents, custom trim in the primary bedroom, and 9-foot ceilings that enhance the sense of space and sophistication. The heart of the home is the beautifully upgraded kitchen, featuring a custom backsplash, specialty hood over the cooktop, farmhouse sink, sleek modern refrigerator, upgraded countertops, and stainless steel appliances, along with a bright breakfast area ideal for casual dining. The kitchen flows seamlessly into the cozy family room, where a shiplap accent wall over the fireplace creates a warm and stylish focal point. Throughout the home, you’ll find custom built-in cabinetry in the pantry and primary closet, adding both functionality and elevated design. The laundry room is thoughtfully finished with custom shelving and trim, making everyday tasks feel anything but ordinary. The primary suite offers a private retreat with a spacious walk-in closet and a beautifully upgraded en-suite bath, featuring a built-in electric fireplace with a stunning shiplap surround—a truly unique and luxurious touch. Step outside to enjoy the well-designed outdoor living space, including a screened-in porch perfect for morning coffee or evening relaxation, and a paver patio ideal for entertaining. The fully fenced backyard offers privacy and space for outdoor activities, pets, or gardening. The additional bedrooms are nicely sized and offer flexibility for guests, a home office, or hobbies. Located just minutes from shopping, dining, and all that Leonardtown has to offer, this home perfectly blends style, comfort, and location. Don’t miss your opportunity to own this one-of-a-kind, designer-inspired home!

Beds:
5
Baths:
3.00
Sq.Ft.:
3,122
Status:
Active
MLS#:
MDSM2030588
Type:
Single Family-Detached
Subdivision:
Schumacher Subd.
Lot size:
11.08 Acres
Year built:
2011
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

MULTIPLE OFFERS RECEIVED! ALL OFFER DUE BY MONDAY MAY 4th at NOON Welcome Home to Your Private Rural Retreat. Nestled on 11 serene, private acres and just steps from St. Mary's River State Park, this stunning 5-bedroom, 2.5-bath Cape Cod offers the perfect blend of country living and modern convenience, all within 15 minutes of Patuxent River Naval Air Station and the charming wharf and dining of Leonardtown. A long gravel driveway with freshly installed bluestone chip leads you to a welcoming front porch. The main floor features an owner's suite with a brand new en-suite bath, two additional bedrooms sharing an updated full bath, a fantastic kitchen with ample storage, and an open family room with a pellet stove. Also on the main level are a dedicated office, a large mudroom/laundry room, and a half bath just off the attached 2-car garage. Upstairs above the garage, two massive additional bedrooms offer incredible flexibility, complete with their own dedicated HVAC system, ideal for guests, teens, or a private home office suite. All HVAC units throughout the home are newer, offering year-round comfort and peace of mind. Step outside to your screened-in back porch and unwind in the hot tub as you take in the tranquil surroundings. When you're ready for more adventure, miles of trails for hiking, fishing, boating, and even hunting are practically at your doorstep. Car enthusiasts and hobbyists will love the detached 2-car garage, currently set up as the ultimate man cave complete with a theater area and gaming space, easily convertible to a workshop. Bonus storage can be found in the attic above the detached garage. The property also features a barn with potential for horse stalls, making it a dream for equestrian enthusiasts or hobby farmers. Whether you're seeking peaceful acreage, outdoor adventure, or a home that truly has it all, this one checks every box. For qualified VA buyers, this home has an assumable VA loan at 2.25%, a rare opportunity in today's market that could mean significant savings on your monthly payment. Don't miss your chance to make it yours.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,624
Status:
Active
MLS#:
MDSM2030516
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.75 Acres
Year built:
2002
Courtesy: Home Towne Real Estate 410-286-9632
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ADDITIONAL INFORMATION

"NO HOA" This charming home offers 1,624 sq. ft. of living space, sits on a generous 3/4-acre lot, and features a new concrete stamped patio perfect for outdoor entertaining.. A true highlight of this property is the presence of Two Primary Suites Primary Suite 1, is an extremely large suite (24' x 19'—including the walk-in closet and attached bath) and features wood laminate floors, crown molding, and a ceiling fan. Attached bath boasts a linen closet, a shower/tub combo, and a nice vanity. Primary Suite 2, offers an attached bath with a tub/shower combo, a ceiling fan, and wood laminate floors. The other two bedrooms are bright and comfortable, featuring ceiling fans and wood laminate floors. The updated hall/guest full bathroom includes a beautiful vanity with ample storage space. The exterior of the property is built for entertainment and practical storage: Large Backyard: Workshop Space: A 12' x 16' metal roof shed is equipped with electric, providing a perfect spot for hobbies or extra storage. Ample Parking: An extended paved driveway ensures plenty of room for guests or multiple vehicles.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,300
Status:
Active
MLS#:
MDSM2030772
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.24 Acres
Year built:
2008
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are greeted by mature landscaping, a large concrete driveway and a sidewalk that takes you to the front porch. Upon entry you are greeted by a nicely sized 2-story foyer. To the right of the center hall, a living room with a formal dining room situated just in behind it. The kitchen, breakfast area, and large family room encompass the entire back portion of the main floor making this the perfect home for entertaining. A nicely finished hall bath and a large mudroom/laundry room complete the main floor. Upstairs, a very large primary suite is home to a huge walk-in closet and an en-suite bath. The bath has dual vanities, a separate water closet, a soaking tub, and a good sized stand up shower. The bathroom once had a water leak at the tub, which has since been mitigated, however was never built back. The bath will require new flooring and a little bit of tile work around the tub. 3 more large bedrooms and a hall bathroom with a double-sink vanity complete the upstairs. The lower level is in good shape with newer vinyl plank flooring, a small wet bar, a recently updated full bath, and a large 5th bedroom. The rec area is also large with two separate areas which creates the ability to have multiple functions. The back yard is large, flat, and it backs to trees allowing for some built-in privacy. Just down the street are all of the community amenities including a village green w/ a gazebo, a large playground, pickleball court, basketball court, and a community center w/ a large community pool! A little paint, some flooring and a few tasteful updates would bring this home back to life! Take advantage now so that you can enjoy all that Leonard's Grant has to offer! Set up a showing ASAP before this one is GONE!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,034
Status:
Active
MLS#:
MDSM2030524
Type:
Single Family-Detached
Subdivision:
Academy Hills
Lot size:
0.2 Acres
Year built:
2004
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Sellers have outgrown this great Leonardtown location without the hustle and bustle of being in down town. Also offered at less than typical Leonardtown homes where the median sold price is $547,500. This 3 bedroom home has been upgraded with new deck/screened porch in 2023, upstairs vinyl flooring, kitchen quartz and new appliances in 2025 & backsplash & new roof. Be in and settled in this one before the next school year. American Home Shield Home Warranty offered too, to make your purchase a sound decision. Come check this one out.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,040
Status:
Active
MLS#:
MDSM2030470
Type:
Single Family-Detached
Subdivision:
Chappelears
Lot size:
0.34 Acres
Year built:
2005
Courtesy: The Southside Group Real Estate 301-298-2892
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ADDITIONAL INFORMATION

Experience waterfront living at its best with this beautifully maintained 2-bedroom, 2.5-bath home with a loft, perfectly positioned along the Potomac River just minutes from historic Leonardtown. Whether you’re looking for a full-time residence or a relaxing getaway, this property delivers the ideal blend of comfort, functionality, and breathtaking views. Designed for those who truly enjoy life on the water, the home features a private pier equipped with a boat lift and fish cleaning station—perfect for boating, fishing, crabbing, or simply enjoying peaceful days on the river. Inside, you’re welcomed by a bright and open layout filled with natural light. The spacious sunroom showcases sweeping water views and creates the perfect space to unwind, entertain, or take in unforgettable sunsets year-round. The open-concept living, kitchen, and dining areas flow seamlessly, making everyday living and hosting effortless. The versatile loft offers additional space that can easily serve as a guest area, home office, or cozy retreat. Two well-sized bedrooms provide comfort and privacy, while the 2.5 bathrooms add convenience for both everyday living and visitors. An oversized 3-car garage ensures plenty of room for vehicles, storage, and all your water and outdoor gear. Located in a peaceful waterfront setting yet just a short drive to Leonardtown’s shops, restaurants, and local attractions, this home offers the best of both worlds—privacy and accessibility. Enjoy quiet mornings by the water, days spent out on the river, and evenings watching the sun set over the Potomac. This is your opportunity to own a true slice of waterfront living in Southern Maryland.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,098
Status:
Active
MLS#:
MDSM2030594
Type:
Single Family-Detached
Subdivision:
Prospect Hill
Lot size:
0.95 Acres
Year built:
1987
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Meticulously cared for rambler, fully updated and move in ready, on nearly one private , partially wooded acre in the waterfront community of The Mulberries at Breton Bay. Brand new engineered hardwood floors plus fresh paint and brand new carpet in all three bedrooms. The kitchen has been updated with a sleek European elegance, white cabinets, granite countertops and stainless steel appliances. Expansive great room with beautiful soaring wood ceiling, propane fireplace, convenient wet bar and mini fridge, offer the timeless backdrop for family gatherings and entertaining. Just down the hall, you will find the family room/sunroom with equal amounts natural light and storage. All the bathrooms are freshly updated to include custom cabinets. The primary bedroom enjoys the corner view of the private backyard to be enjoyed from a private deck. Straight out of a magazine, the primary bath has heated floors, large walk-in shower, free standing tub and double vanity, an owners paradise. Stunning outdoor living space with large screened porch, paver patio with sitting wall and multiple decks providing perfect space for entertaining or sitting quietly while the kids play nearby. Major system upgrades provide peace of mind and long term savings, including newer roof (12/2024), Geothermal HVAC and a whole house generator. Additional highlights include a spacious two-car garage, generous living areas and a setting that offers both privacy and convenience just minutes from downtown Leonardtown all within this quiet water access community. The home comes with entitlement to its own private boat-slip, assigned on individual basis. The community offers a private dock as well as pickleball/tennis/basketball courts. This home will simply not disappoint, as owners attention to detail makes this one shine bright. The thoughtful updates, energy efficiency and lovely outdoor living come together making this an exceptional opportunity. Homes like this don't come along often.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,030
Status:
Active
MLS#:
MDSM2030616
Type:
Single Family-Detached
Subdivision:
Estates At Singletree
Lot size:
0.34 Acres
Year built:
2004
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

Welcome to the completely unforgettable curb appeal of this home situated in the only culdesac of custom homes in the Estates at Singletree! Loved and beautifully maintained from the start by its current owners, they have personally curated, creative florals that surround this Southern Living traditional build, all the way to the perimeters of the property which provide abundant blueberries, raspberries, blackberries, and peaches, for three seasons. Your biggest dilemma is which view to take in from the incredible wrap-around front porch with high ceilings and fully poured, solid concrete floor! Packed with features like a center main hall; main-level living with a bedroom and full bath, breakfast room; counter bar for kitchen-side dining; formal dining room; formal living room/study; open rear floor plan with walk out to deck; and easy access to the yard; side-load oversized garage, and basement; and a huge bedroom or bonus room or second primary bedroom (same size as the 2-car garage!). The custom trims throughout the home merely add embellishment to all of the many other custom details like rounded corners. Please do not try to count the exceptionally large custom windows that fill this home with the most beautiful light, morning to night, which provide gorgeous views of sunrise and sunset - and come with custom blinds as well. Located in the town of Leonardtown, this home is within walking distance to the local college and athletic facilities, healthcare, shopping, restaurants, and the brick town square with street and wharf side park festivals. Do not sleep before scheduling your showing quickly!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,926
Status:
Active
MLS#:
MDSM2030226
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.99 Acres
Year built:
1996
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Charming home located in Leonardtown, offering the perfect combination of privacy and convenience. Situated on a flat 1-acre lot with no HOA, this property gives you space to spread out while still being just minutes from shopping, dining, and everything Leonardtown has to offer. Inside, you’ll find wood floors throughout the entire first level and a bright white kitchen that feels clean and inviting. The layout offers comfortable, functional living, along with a mudroom space just off the garage—ideal for everyday organization. Upstairs, the nicely sized primary suite provides a relaxing retreat, along with the convenience of upper-level laundry. Two additional bedrooms and a full bath complete the upper level. Step outside to enjoy the spacious two-tier composite deck with a hot tub—perfect for entertaining or unwinding. The property also includes a 2-car attached garage, along with a detached garage and shed, offering plenty of storage and workspace options. If you’ve been looking for a home with charm, privacy and a large yard—this is a great opportunity in Leonardtown!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,385
Status:
Active
MLS#:
MDSM2030306
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.37 Acres
Year built:
2012
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to 41389 Holiday Court, a stunning QBH Sotterley model located in the highly sought-after QBH community of Leonard’s Grant! Perfectly positioned on a desirable corner lot, this beautifully maintained 5-bedroom, 3.5-bath home offers the ideal blend of space, functionality, and thoughtful upgrades throughout. Step inside to find gorgeous hardwood floors flowing through the main level, complemented by a private home office, perfect for today’s work-from-home lifestyle. The heart of the home is the grand kitchen, featuring an upgraded oversized island, butlers pantry, abundant cabinetry, and ample space for gathering, entertaining, and everyday living. Just off the kitchen, unwind in the screened-in porch or step outside to the paver patio, creating a seamless indoor-outdoor living experience. The backyard also includes a shed for additional storage and plenty of room to enjoy. Upstairs, retreat to the spacious primary suite complete with a luxurious QBH deluxe shower, offering a spa-like feel. Additional bedrooms provide flexibility for family, guests, or hobbies. The finished basement expands your living space even further with a fifth bedroom and full bath, plus a dedicated theater room—already equipped with projector wiring and surround sound, making it ready for movie nights or game days from day one. Additional highlights include a 2-car side-load garage, generous storage throughout, and a layout designed for both comfort and convenience. Located in the vibrant Leonard’s Grant community, you’ll enjoy sidewalks, community amenities, and a welcoming neighborhood feel—all just minutes from shopping, dining, and local attractions. This home truly has it all—space, upgrades, and a location you’ll love. Schedule your private showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,728
Status:
Active
MLS#:
MDSM2030446
Type:
Single Family-Detached
Subdivision:
Dent
Lot size:
0.15 Acres
Year built:
1940
Courtesy: Evergreen Properties 301-840-8061
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ADDITIONAL INFORMATION

Fully renovated. Move-in ready. Prime downtown location. Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value. Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of the home. Outside, enjoy a fully fenced yard surrounding the property — perfect for pets, gatherings, or private outdoor living. The detached two-car garage adds both convenience and versatility, offering space for vehicles, storage, or even a workshop. All the hard work has been done — just move in and enjoy. Located to downtown shops, dining, and local attractions, this home combines lifestyle, location, and value in one compelling package. Homes like this don’t last — schedule your showing before it’s gone.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,412
Status:
Active
MLS#:
MDSM2030378
Type:
Single Family-Detached
Subdivision:
St Clements Shores
Lot size:
0.28 Acres
Year built:
1940
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Beds:
3
Baths:
4.00
Sq.Ft.:
2,306
Status:
Active
MLS#:
MDSM2030354
Type:
Townhouse
Subdivision:
Clark's Rest
Lot size:
0.08 Acres
Year built:
2019
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome to this stunning end-unit townhome in the highly sought-after Clark’s Rest community. Built in the popular “Compton – Rear Kitchen” model, this home shows like new and delivers the ideal blend of style, space, and functionality. Step inside to a bright, open main level featuring hardwood flooring throughout, abundant natural light, and refined finishes including crown molding and wainscoting. The seamless flow leads to a beautifully appointed kitchen with gas cooking, stainless steel appliances, a large center island, stylish backsplash, and solid surface countertops—perfect for both everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms, including a well-appointed primary suite, two full bathrooms, and the convenience of an upper-level laundry room. The fully finished lower level offers a versatile rec room and an additional full bath—ideal for guests, a home office, or flex living space. Outdoor living is just as impressive with a spacious 18’ x 12’ Trex deck, perfect for relaxing or hosting. Clark’s Rest offers resort-style amenities including a clubhouse, pool, basketball and tennis courts, and a playground—delivering a true community lifestyle. This is turnkey living at its best—schedule your showing today.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,936
Status:
Active
MLS#:
MDSM2029892
Type:
Single Family-Detached
Subdivision:
Cryer
Lot size:
15 Acres
Year built:
2010
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Multigenerationl suite is attached with a full kitchen, laundry room, living room, bedroom and full bathroom.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,368
Status:
Active
MLS#:
MDSM2030498
Type:
Single Family-Detached
Subdivision:
Society Hill
Lot size:
0.48 Acres
Year built:
1963
Courtesy: CENTURY 21 New Millennium 301-609-9000
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ADDITIONAL INFORMATION

Completely renovated and move-in ready, this stunning rambler in desirable Leonardtown is perfectly positioned near Breton Bay Golf Course and the scenic waters of Breton Bay. Every inch has been thoughtfully updated... brand new roof, windows, heat pump, water heater, washer & dryer, appliances, encapsulated crawl space... nothing to worry about for the years to come, offering a truly turnkey experience. The designer kitchen shines with quartz countertops, stainless steel appliances, island with additional seating, pendant lighting, and extensive recessed lighting, opening to a bright and inviting living space and dining nook. Featuring 3 bedrooms, 2 full baths with exquisite tiling details, a spacious level yard, and a 1-car garage... this home effortlessly blends style, comfort, and quality craftsmanship throughout. Schedule your showing today!

Beds:
9
Baths:
5.00
Sq.Ft.:
6,476
Status:
Active
MLS#:
MDSM2030418
Type:
Single Family-Detached
Subdivision:
Greenwood Hills
Lot size:
2.1 Acres
Year built:
2012
Courtesy: Samson Properties 703-378-8810
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ADDITIONAL INFORMATION

From the moment you enter over 6000+ sqft of finished home , it's clear this home has been enhanced well beyond the typical. High-quality finishes, updated systems, and carefully selected improvements are evident throughout, creating a move-in-ready experience that today's buyers will immediately appreciate. This meticulously maintained home features luxury living on 2.10 acres, offering the serenity of rural living with the convenience of modern amenities and endless upgrades. Located in the heart of Leonardtown, this HOA-free property offers the perfect blend of comfort, convenience, and exclusivity. The layout is equally impressive, maximizing space in all the right ways. Generous room sizes, well-defined living areas, and an intuitive flow provide both everyday comfort and the flexibility to suit a variety of lifestyles. Whether gathering in the main living areas, working from home, or hosting guests, each space feels purposeful and well-proportioned. The kitchen and adjoining living spaces serve as the heart of the home, offering both functionality and connection- ideal for modern living. Additional finished areas expand the home's livability, while abundant storage ensures everything has its place. Enjoy the peaceful views of the adjacent farmland from your screened porch (12' x 20') or while lounging by the expansive saltwater pool (20' x 40') complete with a slide, fence, and safety gate. THE CEILING FANS HAVE BEEN REPLACED WITH BEAUTIFUL CRYSTAL CHANDELIERS. This home is adorned with high-end finishes and upgrades, including hard flooring throughout (mostly hardwood and ceramic tile), lofty 9' ceilings, elegant crown molding, a double-sided gas fireplace, and the convenience of soft-close cabinets/drawers. Additionally, the home features wood blinds adorning every window in the house and garage, complemented by wood plantation shutters on exterior doors and master bedroom windows. **SLEEK KITCHEN** The expansive kitchen features granite countertops, a generously sized island, abundant storage and cabinet space, double ovens, a 5-burner gas cooktop, a built-in InSinkErator instant hot water dispenser, and a huge walk-in pantry (6' x 6.5').Unwind in the luxurious master suite, complete with a cozy gas fireplace, double-pane windows, a graceful tray ceiling, and a vaulted walk-in closet adorned with custom built-ins. Pamper yourself in the spa-like ensuite bathroom featuring a spacious double shower, a built-in vanity, and abundant cabinet space. Plus, discover endless potential in the attached 17' x 8' bonus room with three windows, secluded by French doors, perfect for transforming into a workout room, office, nursery, and beyond! **BONUS AMENITIES** Additional highlights include an oversized 3-car garage with a CAR LIFT. JAN 2022 - New Heat Pump & Gas Furnace (full HVAC replacement) JAN 2022 - Air Scrubber by Aerus (integrated with HVAC) MAY 2022 - Radon Mitigation System Installed SEP 2022 - New Refrigerator FEB 2024 - House Interior Professionally Re-Painted MAR 2024 - Septic Tank Pumped (done every year) MAR 2024 - New Closet Flooring MAY 2024 - New Roof MAY 2024 - Power Wash House, sidewalks, pool MAY 2024 - New Hayward Pool Pump MAY 2024 - New Porch Screens JUN 2024 - Driveway Sealed Finished Basement with additional 4 huge bedrooms and 2 Full baths perfect for rental/in-law suite and beautiful large kitchen with stainless steel appliances and granite countertop and back splash for living/recreational use. One of a kind home!!!!

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Leonardtown Real Estate

Leonardtown is located in Maryland. Leonardtown, Maryland has a population of 4,445. Leonardtown is more family-centric than the surrounding county with 66.19% of the households containing married families with children. The county average for households married with children is 35.05%.

The median household income in Leonardtown, Maryland is $126,472. The median household income for the surrounding county is $102,859 compared to the national median of $69,021. The median age of people living in Leonardtown is 32.3 years.

Leonardtown Weather

The average high temperature in July is 87.8 degrees, with an average low temperature in January of 28.4 degrees. The average rainfall is approximately 45.5 inches per year, with 14.3 inches of snow per year.

Leonardtown Map

Leonardtown Real Estate Market Conditions

  • Median sales price

    $519,900
    12.7%
    change since last quarter
  • # Active listings

    54
    30-day change

Leonardtown Schools and Demographics

Education near Leonardtown, MD

City County
High School Graduates 86.69 91.67
College Degree - 2 year 4.14 7.83
College Degree - 4 year 43.83 33.03
Graduate Degree 20.41 11.79
Expenditures per Student 15,242 15,242
Students per Teacher 15.9 15.9

Elementary Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Benjamin Banneker Elementary School PK - 05 683 15 20656
Evergreen Elementary School PK - 05 795 19.3 20619
George Washington Carver Elementary School PK - 05 644 17 20634
Greenview Knolls Elementary School PK - 05 408 17.9 20634
Leonardtown Elementary School PK - 05 789 18.6 20650
Piney Point Elementary School PK - 05 529 18.7 20690

Middle Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Leonardtown Middle School 06 - 08 933 15.9 20650

High Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Great Mills High School 09 - 12 1,549 17.8 20634
Leonardtown High School 09 - 12 1,831 20.8 20650

Ungraded Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Dr. James A. Forrest Career and Technology Center UG - UG 0 0 20650
St. Mary's County Evening High UG - UG 0 20650

Demographics near Leonardtown, MD

City County
Neighborhood Type Small town
Population 4,445 113,209
Population Density 1,169 316
Median Age 32.3 36.7
People per Household 2.8 2.8
Median Household Income 126,472 102,859
Average Income per Capita 41,923 44,208

Real estate near Leonardtown