Leonardtown MD Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
2,507
Status:
NEW LISTING
MLS#:
MDSM2029800
Type:
Single Family-Detached
Subdivision:
Society Hill
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:
4
Baths:
4.00
Sq.Ft.:
3,299
Status:
NEW LISTING
MLS#:
MDSM2029898
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.38 Acres
Year built:
2008
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Beautiful Compton model on a half acre lot. Finished Basement with ample storage space as well. Lovely built in pool with a fenced in backyard. Composite Deck covered with a gazebo. New Paint, New carpet.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,482
Status:
Active
MLS#:
MDSM2029912
Type:
Single Family-Detached
Subdivision:
Estates At Singletree
Lot size:
0.45 Acres
Year built:
2005
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Beautiful 5BR, 3BA home with over 3,100 sq ft above grade tucked away on a peaceful ½-acre flag lot backing to trees in the heart of Leonardtown. Inside you’ll find hardwood flooring, spacious living areas, and a warm, inviting family room perfect for everyday living or entertaining. The kitchen features granite countertops, stainless steel appliances, and plenty of workspace. The main level includes a private guest suite with full bath and second laundry, ideal for visitors, multigenerational living, or a home office. Upstairs offers a large primary suite with its own fireplace, generously sized bedrooms with large closets, and a 15x11 bonus room perfect for a playroom, rec room, or second family space. Enjoy the outdoors with a 10x10 screened porch, two patios, fenced garden/play area, and shaded backyard. Walk to Leonardtown Square, hospital, shopping, and restaurants. Short commute to NAS Pax River. Located in the highly sought-after Leonardtown school district.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,056
Status:
Active
MLS#:
MDSM2029808
Type:
Single Family-Detached
Subdivision:
Leonardtown
Lot size:
1 Acres
Year built:
1995
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Charming Leonardtown Rambler on a Full Acre. Move-In Ready! Welcome home to the house you've been waiting for. Whether you're buying your first home or rightsizing into something smarter, this meticulously maintained 2-bedroom, 2-bath rambler delivers the Leonardtown lifestyle without the big-house headaches. Freshly painted throughout, walls and ceilings, the home features luxury vinyl plank flooring, a spacious living room, and a large country kitchen with a comfortable eat-in area. An enclosed front porch offers the perfect place to relax year-round. Washer and dryer convey, and new ceiling fans along with updated lighting in the kitchen and hallway complete the interior. The current owners cared for this home the way every homeowner hopes the previous one did. The HVAC system has been professionally serviced every six months as part of a maintenance plan, ensuring every major system has been consistently maintained. Outside, the property continues to impress with a brand new Trex deck and ramp, blue stone walkway a basketball hoop that conveys, a 10x12 shed with a concrete floor, a second 8x8 shed for additional storage, and a full acre of land with room to spread out and enjoy. A children's playset is also available for purchase. Major Improvements Include: • 2026: Both bathroom vanities replaced • 2024: New Trex deck and ramp • 2019: New asphalt driveway • 2021: HVAC system replaced • 2018: Crawl space fully encapsulated with Dehumidifier • 2019: New roof and siding on the home, plus new roof and siding on both sheds • 2018: Bathroom updates with luxury vinyl plank flooring • Fresh paint throughout, walls and ceilings last month • HVAC professionally serviced every 6 months • New ceiling fans and updated lighting in the kitchen and hallway Homes like this in Leonardtown do not sit on the market long. Schedule your showing today before someone else does.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,410
Status:
Active
MLS#:
MDSM2029700
Type:
Single Family-Detached
Subdivision:
Breton Bay Landing
Lot size:
0.51 Acres
Year built:
1993
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

BEST AND FINAL DUE 3/13 BY 4PM. Gorgeous Colonial in Breton Bay! This welcoming home is nestled on a quiet cul-de-sac, steps away from the great amenities this desirable community has to offer. Start your tour of this 4-bedroom, 3.5-bath home by opening the attractive glass front door, and stepping across stunning hardwood floors, refinished just last year. Pass the formal living room, perfect for conversations, or a good book. Or make it into a home office, because there's plenty of space for gathering in the open-concept family room, dining area and kitchen. Serve VIP guests in the formal dining room. High-end cabinets enhance the beauty of a kitchen featuring granite counters, stainless appliances, a breakfast bar, wine rack/micro-fridge and soft-close drawers. Marvel at the Induction Range's cool burner after boiling water in minutes. The informal dining area leads out to the back porch and paver patio, a set up that's great for entertaining indoors and out. The family room has custom built-in shelving, and a brick-hearth pellet stove, adding warmth to those chilly nights. Enter the Primary Bedroom through an ante room that makes a great nursery, sitting room, workout/hobby room, or office. A cathedral ceiling rises above the spacious primary. In the primary bath, relax in the soaking tub with marble surround. The lower level is fully finished with a rec room, bedroom, full bath, and storage. Grow fresh veggies and flowers in the multiple raised garden beds out back, and play games in the level yard. This wonderful home's "extras" include a 2-car garage with shelf storage and utility sink, an over-size 80-gallon water heater, gutter guards, a shed, and an invisible fence for the pups. Up the hill, enjoy a round of golf at the Breton Bay public golf course, or become a member, and take a swim at the pool and get in a few sets of tennis. Down the hill, picnic at the community beach, play on the playground, fish & crab off the dock, or slip a kayak in for a paddle. Located in the Leonardtown school district, and minutes from shopping and main commuter routes, this cul-de-sac Colonial should be a must-see on your list. Request your showing today!

Beds:
3
Baths:
3.00
Sq.Ft.:
3,012
Status:
Active
MLS#:
MDSM2029774
Type:
Single Family-Detached
Subdivision:
Society Hill
Lot size:
0.64 Acres
Year built:
1978
Courtesy: Keller Williams Realty 703-679-1700
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ADDITIONAL INFORMATION

Stunning Contemporary Home in Society Hill Community This exquisite contemporary-style home is located in the desirable Society Hill community of Leonardtown. The main level features a formal living room with a soaring cathedral ceiling, built-in shelving, and a wood-burning fireplace, offering a warm and inviting atmosphere. The formal dining room is ideal for entertaining, while the chef’s kitchen boasts a center island, cooktop, double wall ovens, and a stylish tiled backsplash. Upstairs, the primary bedroom provides a spacious retreat with a full ensuite bath. Two additional generously sized bedrooms share a full hall bath. The finished basement includes an open family/rec/entertainment room with a walk-out to a secluded backyard, perfect for outdoor relaxation. The property also features a 2-car attached garage with ample additional driveway parking and a rear deck that overlooks mature trees, offering a peaceful and private setting. This home is conveniently located just minutes from downtown Leonardtown and offers a short commute to PAX River Naval Base. While there is no HOA, residents have the option to join the Brenton Bay Community Association for access to a private beach, pool, tennis courts, and a golf course. Don’t miss the opportunity to make this beautifully designed home your own! Photos may be virtually staged

Beds:
4
Baths:
3.00
Sq.Ft.:
2,176
Status:
Active
MLS#:
MDSM2029434
Type:
Single Family-Detached
Subdivision:
Breton Bay/society Hill
Lot size:
0.61 Acres
Year built:
1976
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome to this beautifully maintained contemporary home in the sought-after Society Hill section of Breton Bay, offering privacy, space, and timeless character on a generous .60-acre lot. From the moment you step inside, you’re greeted by soaring two-story ceilings in the great room, highlighted by rich hardwood floors and a striking stone gas fireplace that creates a warm and inviting focal point. The updated kitchen features granite countertops, distinctive wood ceilings, and seamless flow into the combined dining and living areas. A main-level bedroom and full bath provide flexible living options for guests or multigenerational needs. Upstairs, you’ll find two additional bedrooms and a full bath, while the finished basement expands the living space with another bedroom and full bath, perfect for a private suite, home office, or recreation area. The screened-in porch overlooks the peaceful, private backyard, offering the perfect setting to relax and enjoy the natural surroundings. Major updates, including replacement windows, & siding within the last five to six years and a brand-new heat pump installed in 2026 and a new roof last year, provide added comfort and peace of mind. Located just minutes from downtown Leonardtown, waterfront amenities, and Breton Bay’s golf and marina lifestyle, this home offers the perfect blend of convenience, charm, and modern updates.

Beds:
n/a
Baths:
Sq.Ft.:
2,184
Status:
Active
MLS#:
MDSM2029078
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
8.43 Acres
Year built:
1974
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

This great 8+ acre property with scenic pasture views. Solid 4 bedroom rambler on full basement. So many possibilities.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,724
Status:
Active
MLS#:
MDSM2029722
Type:
Single Family-Detached
Subdivision:
Clark's Rest
Lot size:
0.22 Acres
Year built:
2016
Courtesy: Keller Williams Realty/Lee Beaver & Assoc. 703-330-2222
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ADDITIONAL INFORMATION

Welcome Home! 41377 Doctors Crossing Rd is a well-maintained home located in the sought-after Clark’s Rest community — where comfortable living meets a vibrant neighborhood lifestyle, with a pond just steps away and walking distance to the clubhouse. Offering 5,538 total square feet, including 3,724 finished square feet above grade, this home provides the space and flexibility. As you step through the front door, you’re welcomed by a beautiful two-story foyer and 9-foot ceilings that immediately create a sense of openness and natural light. The main level features a bedroom and a full bathroom, perfect for guests, multigenerational living, or a private home office. This flexible space adds everyday convenience and is a feature many buyers actively look for but rarely find. Moving through the home, the generous living areas provide plenty of room for both everyday life and entertaining. Picture family dinners, weekend gatherings, and cozy evenings in spaces designed to bring people together while still allowing everyone room to spread out. Imagine daily meals, morning coffee accompanied by a serene, wooded view—a private, lush backdrop where you can watch your loved ones playing, sledding down a snowy hill just steps from your backyard. Upstairs, you’ll find 4 spacious bedrooms throughout, including a massive primary suite that truly feels like a private retreat. With plenty of room for a king-size bed and a sitting area, it’s the perfect place to unwind at the end of the day. The primary bathroom offers ample space for daily routines and relaxation. Another upstairs bedroom features its own private bathroom, ideal for guests or anyone who appreciates extra privacy. All additional bedrooms are generously sized, offering comfort and flexibility for family members, hobbies, or work-from-home needs. The unfinished basement with rough-in plumbing provides 1,814 square feet of future potential. Whether you envision a recreation room, home gym, theater, or an additional bedroom, the groundwork is already in place to expand as your needs grow. Step outside and the lifestyle continues. A peaceful pond just steps from the front door offers the perfect setting for morning walks or relaxing evening sunsets. Living in Clark’s Rest means enjoying exceptional community amenities, including a clubhouse, two swimming pools with a shaded kiddie pool, multiple playgrounds, tennis courts, basketball court, volleyball area, and two gravel nature trails. Throughout the year, the community hosts pool opening and closing parties, holiday celebrations, and neighborhood events that bring neighbors together and create a welcoming atmosphere. It's also conveniently located just minutes from Downtown Leonardtown, shopping centers, restaurants, MedStar St. Mary’s Hospital and St. Mary’s River State Park (St. Mary’s Lake). Easy access to major commuter routes including MD-235, 234, Rt5 and a short drive to Naval Air Station Patuxent River (NAS Pax River). Don’t wait — schedule your showing today! 41377 Doctors Crossing Rd is ready to welcome you home. ???

Beds:
4
Baths:
3.00
Sq.Ft.:
2,500
Status:
Active
MLS#:
MDSM2029728
Type:
Single Family-Detached
Subdivision:
Hawks Nest
Lot size:
1.34 Acres
Year built:
2025
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and entertaining. The gourmet kitchen is the heart of the home, boasting quartz countertops, stainless steel appliances, and stunning two-tone shaker cabinetry that combines warmth and sophistication. A spacious center island offers additional prep space and seating, all overlooking the expansive living and dining areas. Upstairs, the oversized primary suite offers a peaceful retreat with a generous walk-in closet and a spa-like en-suite bath featuring dual vanities, a custom tile shower, and sleek black fixtures. Two additional bedrooms, a full bath, and a convenient laundry room complete the upper level. With a two-car garage, no HOA, and a private, wooded setting just minutes from Leonardtown’s charming town square, waterfront attractions, shops, and restaurants, this home offers the best of Southern Maryland living. Don’t miss the opportunity to make this stunning new home your own.

Beds:
4
Baths:
4.00
Sq.Ft.:
5,454
Status:
Active
MLS#:
MDSM2029030
Type:
Single Family-Detached
Subdivision:
Avenmar
Lot size:
3.62 Acres
Year built:
2001
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Avenmar beauty situated on over 3.5 acres, offering exceptional space and privacy. The custom kitchen features top-of-the-line appliances, custom cabinetry, solid-surface countertops, and stunning light fixtures. The main level includes formal dining and living rooms, a dedicated office space, and a two-story family room with an overlook from above. Floor-to-ceiling windows showcase peaceful wooded views, and a gas fireplace anchors the family room with warmth and style. The second level offers a spacious primary suite with a separate sitting room and an ensuite bath. Three additional bedrooms share a beautifully updated full bath featuring custom tile and cabinetry. A conveniently located laundry room is also on the bedroom level. A back staircase off the kitchen provides easy access to both sides of the second floor. Outdoor living shines with a new composite deck off the back, while the welcoming front porch overlooks the expansive front yard. The walk-out basement includes a finished full bath, with the remaining space ready for the new owner to customize. A Tesla solar roof adds energy efficiency and modern appeal.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,526
Status:
Active
MLS#:
MDSM2029578
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.38 Acres
Year built:
2003
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

?? Seller is offering a $4,000 concession with an accepted full-price offer! Use it for an interest-rate buy-down, closing costs, or to add your own personal touches. Get ready to fall in love with this wonderful 5BR/3.5BA home in the Leonardtown's Kingston Estates! Set on a peaceful, no-through street and perched on a gentle hill, this home offers great privacy with mature trees, plenty of open yard space and no rear neighbors. Inside, the two-story foyer opens to a main level with newer flooring, real hardwood floors in the living room, and fresh paint throughout the home. A flexible room with French doors at the front of the house works perfectly as a home office or formal dining room. The eat-in kitchen features marble countertops, a tile backsplash, stainless GE appliances, a Kraus sink, center island, and a spacious pantry. It opens directly to a cozy family room with a wood-burning fireplace—great for gathering. Upstairs, you’ll find four generously sized bedrooms. The primary suite offers wooded views, a soaking tub, dual sinks, walk-in shower, and a large linen closet. Three additional bedrooms and a second full bathroom complete the upstairs. The fully finished walkout basement adds even more versatility with a fifth bedroom, full bath, wet bar, laundry area, and a fantastic flex room ideal for a gym, playroom, office, or media space. Outdoor living is another highlight. Enjoy the composite screened deck that overlooks a private backyard backing to a Forest Conservation Area. A small fenced section is perfect for pets, and the property includes two great sheds—one heated and cooled, ideal for hobbies or studio use, and a 20'×24' Amish-built structure with electric and lofts for storage or a workshop. Lovingly maintained by its original owners, the home also includes valuable big-ticket updates such as two high-efficiency HVAC systems (2023 & 2025), an architectural roof (2018), a rebuilt driveway, whole-home filtration system, sump pump with backup, chimney improvements, and updated bath fixtures. With more than 3,500 sq ft of finished space and a welcoming, flexible layout, this home offers comfort, privacy, and long-term value—just minutes to historic Leonardtown, dining, shopping, and an easy commute to PAX River Naval Base. You’ll feel right at home the moment you arrive. Come and take a look!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,402
Status:
Active
MLS#:
MDSM2029470
Type:
Townhouse
Subdivision:
Clark's Rest
Lot size:
0.05 Acres
Year built:
2020
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

Open House Sat March 21st and Sun March 22nd from 1:00-3:00pm. Welcome home to Marwood Circle in the desirable Clark's Rest Neighborhood of Leonardtown. This nearly new townhome built in 2020 has over 2400 square feet of living space and is in move in condition. Nice open concept on the main level includes an updated kitchen with granite countertops and island, stainless appliances and pantry, large family room, separate dining area and half bath. On the upper level you will find the spacious primary bedroom with en-suite bath, two spare bedrooms, full bath and upstairs laundry for added convenience. The fully finished lower level includes a nice rec room/office/craft room with full bath. The two car garage is spacious with extra driveway parking as well. An all composite deck is off the kitchen for grilling and entertaining. The neighborhood has a nice community clubhouse which can be used by residents for parties, etc, large community pool, basketball and tennis courts and tot lot. Close to historic downtown Leonardtown where you will find numerous restaurants, quaint shops and the Leonardtown Wharf to explore. There is also a free trolley in the summer and for special downtown events on the square which has a convenient stop right within the neighborhood. Schedule your appointment today!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,114
Status:
Active
MLS#:
MDSM2029528
Type:
Single Family-Detached
Subdivision:
Leonardtown
Lot size:
1 Acres
Year built:
2002
Courtesy: CENTURY 21 New Millennium 443-968-9595
View additional info

ADDITIONAL INFORMATION

MOVE-IN READY!! Welcome to this beautifully maintained 4-bedroom, 2-bath rambler situated on a 1-acre lot in Leonardtown, Maryland. Offering the ease of one-level living and a functional, flowing floor plan, this home combines space, comfort, and practicality in a peaceful Southern Maryland setting. Step inside to find a spacious living room with gleaming floors and abundant natural light. The kitchen features stainless steel appliances, ample cabinetry, and generous counter space, opening conveniently to the dining area with French doors leading to the rear deck—perfect for entertaining or enjoying the wooded backdrop beyond the fully fenced back yard. All four bedrooms are generously sized, including a large primary suite with a private bath. The secondary bedrooms offer flexibility for guests, home offices, or hobbies. Storage is abundant throughout, highlighted by an impressive oversized pantry room complete with built-in shelving—ideal for bulk storage, small appliances, or organized household essentials. Additional features include a separate laundry room, utility space, attached 2-car garage, and plenty of room to spread out both inside and out. The 1-acre lot provides privacy while still being conveniently located near downtown Leonardtown, schools, shopping, and commuter routes. If you’re looking for space, storage, and single-level living in St. Mary’s County, this Leonardtown rambler checks all the boxes.

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2029488
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

Homesite #99 Madison D3: ****ALMOST READY FOR MARCH DELIVERY***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 2,604 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:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2029486
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

Homesite #101 Madison D3: ***ALMOST READY FOR MARCH DELIVERY***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 2,604 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:
5
Baths:
4.00
Sq.Ft.:
4,180
Status:
Active
MLS#:
MDSM2029268
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.45 Acres
Year built:
2010
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Tucked away at the end of a quiet cul-de-sac in sought-after Leonard’s Grant, this stately brick-front home offers space, upgrades, and an exceptional setting on nearly half an acre. Step inside to a spacious, well-designed layout featuring a private first-floor office—ideal for working from home. The upgraded kitchen serves as the centerpiece of the home. There is ample cabinetry, a double door pantry, nice prep space, and a butler’s pantry with a built-in wine rack, perfect for entertaining and everyday convenience. Upstairs, the expansive primary suite provides a true retreat with a massive walk-in closet, while the additional bedrooms are all generously sized, offering comfort and flexibility for family or guests. The fully finished basement adds even more living space, featuring a dedicated theater area, a 5th bedroom, and a full bath—perfect for guests or extended stays. A versatile utility room is currently being used as a dance studio, and there is still plenty of unfinished storage space. Outdoor living is just as impressive, with a large composite deck overlooking the nearly half-acre backyard, plus a custom paver patio with a built-in fire pit—ideal for relaxing evenings or hosting gatherings. Additional features include a radon mitigation system already in place and a prime location within the community. Enjoy all that Leonard’s Grant has to offer, including a pool, clubhouse, playgrounds, and more—all just minutes from Leonardtown’s shops, restaurants, and waterfront.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,571
Status:
Active
MLS#:
MDSM2029208
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

Homesite 100 Madison D1: *** Mid March Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 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 white kitchen cabinets, Quartz countertops, subway tile backsplash, black 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:
3
Baths:
4.00
Sq.Ft.:
2,764
Status:
Active
MLS#:
MDSM2029148
Type:
Townhouse
Subdivision:
Leonardtown Landing
Lot size:
0.05 Acres
Year built:
2005
Courtesy: EXP Realty, LLC 888-860-7369
View additional info

ADDITIONAL INFORMATION

Experience life in a charming waterfront community where every day feels like a getaway. Enjoy kayaking, paddleboarding, and a variety of outdoor activities right at your doorstep. Start your mornings with yoga on the wharf or take a short stroll to the square for weekend concerts and local events. Located in the heart of Leonardtown, this home offers not only convenience but a vibrant lifestyle in one of the area’s most desirable settings. Inside, you’ll find thoughtful features designed for comfort and ease,including a private elevator, perfect for transporting groceries, laundry, and more between floors. With five spacious decks and porches, you’ll have plenty of opportunities to relax and take in the beautiful surroundings. Just steps from the waterfront community park and close to everything you need, this exceptional home truly has it all. Don’t miss your chance to make it yours. This is a must-see!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,829
Status:
Active
MLS#:
MDSM2028808
Type:
Single Family-Detached
Subdivision:
Breton Bay Estates
Lot size:
0.51 Acres
Year built:
1965
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

BACK ON MARKET. Charming Split Level home on just over 1/2 an acre in Breton Bay. As you enter the front door, the hardwood floors lead you throughout the main living areas of the home. Living room and dining room are both located on the main level. Kitchen with updated Corian counters and stainless appliances. Back door off kitchen opens to patio and back yard. Great entertaining space or space to relax and enjoy a cocktail. Primary bedroom with bathroom. Two additional bedrooms and a full hall bathroom complete the upper level. The lower level of the home has a rec room w/fireplace, half bathroom, laundry/utility room and outside access to the back yard. New holding tank is being installed. Located close to schools, shopping, and area amenities. Easy drive to downtown Leonardtown. Enjoy a round of golf, tennis or a swim in the pool by joining the Breton Bay Golf & Country Club. Schedule your online appointment today.

Beds:
n/a
Baths:
Sq.Ft.:
1,691
Status:
Active
MLS#:
MDSM2028632
Type:
Other
Subdivision:
Leonardtown Town Center
Lot size:
0.57 Acres
Year built:
1940
Courtesy: Infinitas Realty Group 240-925-2224
View additional info

ADDITIONAL INFORMATION

Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits. Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts & Entertainment environment, this site offers flexibility for buyers with vision. Prior use history and prime location may support creative redevelopment concepts—buyers are encouraged to submit plans and ideas directly to the Town of Leonardtown for consideration. Ideal for those seeking a downtown setting close to the waterfront, shops, dining, and year-round community events. Whether envisioning a custom residence, small-scale residential development, or a thoughtfully designed project consistent with the surrounding neighborhood, this property presents a rare opportunity to shape a lasting presence in one of Southern Maryland’s most vibrant town centers. Property sold as-is. Hold Harmless Agreement required prior to viewing. Buyers to perform all due diligence regarding zoning, development potential, and Town approvals.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,080
Status:
Active
MLS#:
MDSM2028586
Type:
Single Family-Detached
Subdivision:
Leonardtown Farms
Lot size:
0.83 Acres
Year built:
2012
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome to 21345 Fairwood Court! Thoughtfully updated and meticulously maintained, this move-in-ready home in the desirable Leonardtown Farms community offers space, layout, and functionality. With 5 bedrooms on the upper level, 3.5 bathrooms, and generous living spaces on every level, there is room to grow, gather, and truly settle in. Beautiful landscaping welcomes you to the covered front porch and into an open foyer, flanked by a formal sitting room and dining room. A dedicated office provides an ideal work-from-home space and flows into the large family room. The updated kitchen features new Zellige tile backsplash, granite countertops, updated stainless steel appliances, an island with sink, cooktop, built-in microwave, wall oven, and a dinette area. New LVP tile flooring, refinished hardwood floors enhances the main level, and new carpeting has been installed on main level and stairs. The spacious family room with gas fireplace is perfect for cozy evenings. The kitchen opens to an updated patio and fire pit, creating an inviting backyard space for entertaining family and friends. The primary suite offers two walk-in closets, a soaking tub, separate shower, dual vanities, and a private bathroom. The finished lower level provides exceptional flexibility, featuring a large open sitting area, a room currently used as a gym (previously a theater room), an additional flexible room suitable for a bedroom, guest space, or hobby room, two storage rooms and a full bathroom. A covered exterior stairwell provides convenient access to the basement. This one won't last long!

Beds:
5
Baths:
3.00
Sq.Ft.:
3,464
Status:
Active
MLS#:
MDSM2028400
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
View additional info

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:
4
Baths:
4.00
Sq.Ft.:
3,308
Status:
Active
MLS#:
MDSM2027022
Type:
Single Family-Detached
Subdivision:
Clark's Rest
Lot size:
0.15 Acres
Year built:
2024
Courtesy: RE/MAX Realty Group 301-843-5100
View additional info

ADDITIONAL INFORMATION

Welcome to your dream home, the Pinehurst model built by Marrick Homes, nestled in the highly sought-after Clark's Rest Community. From the moment you pull into the driveway, this timeless Colonial immediately impresses with its classic charm and spacious, modern living. This 3/level home offers 4/bedrooms, 3.5 baths with 4,664 sq ft of living space. The spacious front-load 2-car garage includes an EV charger for your convenience. Step through the front door into a two-story foyer, where natural light floods the space and sets the tone for an elegant yet welcoming home. To your right, the formal living room offers a perfect place for quiet gatherings, while the formal dining room to your left is ideal for hosting holidays and dinner parties. Continue into the heart of the home is an open-concept family room with a cozy fireplace, seamlessly connected to the morning room and a truly spectacular gourmet kitchen. At the center is an impressive long kitchen island, offering abundant seating and serving as the perfect gathering space for family and guests alike. surrounding it, you'll find 42" upgraded cabinetry, quartz countertops, a stylish tile backsplash, stainless steel appliances, gas stove, and a generous walk-in pantry- a chef's dream and an entertainer's delight. Tucked away on the main level, you'll also find a private library perfect for a home office, a flex room ideal as a playroom or guest space, and a convenient separate laundry room just steps from the garage. Upstairs, the oversized primary suite is a true retreat. Unwind in the spa-like en suite bath, complete with dual walk-in closets, a 5x5 tile shower with dual showerheads, a soaking tub, dual vanities, and a private water closet. Three additional bedrooms offer ample space for family, and guests, one includes its own private full bath, while the other two share a beautifully appointed hall bath. The unfinished walkout basement offers tall windows and a 3-piece bathroom rough-in, giving you a blank canvas to create even more living space tailored to your needs. Whether it's a home gym, media room, or guest suite, the possibilities are endless. Outside, enjoy the level backyard-perfect for play, pets, or outdoor entertaining. Throughout the home, you'll find luxury vinyl plank flooring, upgraded lighting, and ceiling fans, adding style and comfort to every room. This is more than a house-it's a place to live, grow, and make lasting memories. Come see why life in Clark's Rest, with community amenities including a pool, clubhouse, and walking trails, is the perfect place to call home.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,026
Status:
Active
MLS#:
MDSM2026838
Type:
Single Family-Detached
Subdivision:
St Marys
Lot size:
2.02 Acres
Year built:
1961
Courtesy: Keller Williams Legacy 443-660-9229
View additional info

ADDITIONAL INFORMATION

*Back on the market. A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities for both homebuyers and investors, driven by its growing real estate market and strategic economic initiatives over the years. This property may be best suited for an investor or seasoned buyer who has the vision and capacity to restore it with some well-deserved TLC. This single-family ranch-style home features 3 bedrooms and 1 bathroom. Built in 1961, it offers approximately 1,026 square feet of living space and is situated on a 2.02-acre lot. This home also includes a detached garage with space for two vehicles. For investors, the property's sizable lot and ranch-style design may offer potential for renovation or expansion. The absence of a homeowner’s association (HOA) could also provide additional flexibility for property modifications. Nearby schools include Piney Point Elementary School, Leonardtown Middle School, and Leonardtown High School.

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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

    31
    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