Leonardtown MD Real Estate & Homes for Sale

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Beds:
4
Baths:
4.00
Sq.Ft.:
2,571
Status:
NEW LISTING
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: ***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:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
MDSM2029202
Type:
Townhouse
Subdivision:
Meadows At Town Run
Lot size:
0.08 Acres
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Homesite 102 Oakley D1***March Delivery***Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft 4 Bedrooms 3.5 Baths 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The first floor level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bath and access to your fenced backyard, ideal for guests, a private office, or a second living space. The oversized one-car garage and wide driveway provide ample parking and storage options. Upstairs, you'll find 9’ ceilings, luxury vinyl plank flooring, and a beautifully appointed kitchen with 42” upgraded maple cabinetry, slide-out dovetail drawers, soft-close features, and quartz countertops. The large center island, walk-in pantry, stainless steel GE appliances, and open-concept layout make this a true entertainer’s dream. The adjoining dining and family rooms lead out to a 14x12 maintenance-free deck overlooking your vinyl-fenced backyard. The upper level includes a luxurious owner’s suite with a tray ceiling, walk-in closet, and ensuite bath featuring dual vanities and QBHI’s signature deluxe tiled shower with bench, dual showerheads, and recessed lighting. Two additional bedrooms, a full hall bath, and a separate laundry room complete the top floor. Additional highlights include: finished and painted oversized garage, smart home technology with touchscreen IQ Pro command center, Skybell video doorbell, and smart thermostat, sodded and landscaped yard, stone-to-grade front, concrete front porch, and seamless gutters, 6’ vinyl fenced backyard with gate. Community amenities include clubhouse, pool, playground, tennis courts, and pickleball courts. Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,136
Status:
NEW LISTING
MLS#:
MDSM2029090
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2015
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome to the perfect blend of elegance, comfort, and location—this gorgeous Leonard's Grant home truly has it all and shows like a model. Meticulously maintained and move-in ready, this home offers 5 full bedrooms and 3.5 baths with a thoughtfully designed floor plan with plenty of room at 3,824 sq ft of finished space. The gourmet kitchen features a wall oven, gas cooktop, gorgeous cabinetry, and a convenient desk/workstation area. Hardwood floors run throughout the main level, with the exception of the cozy family room, which includes carpet and a gas-burning fireplace. A large breakfast nook with sliding doors leads to the deck and a charming fenced in backyard complete with a firepit, perfect for relaxing or entertaining. The main floor also includes two separate office spaces—one with French doors, and the other flexible enough to be used as a formal dining room, kids’ play area, or additional office. Upstairs, the spacious primary suite offers two walk-in closets and a luxurious en-suite bath with a walk-in shower, double vanities, and a soaking tub. All additional bedrooms are generously sized. The finished basement includes a rec room, full bath, and bedroom, along with an unfinished area ideal for a home gym or extra storage. Ideally located just minutes from all the restaurants, shops, and amenities Leonardtown has to offer, this home combines everyday convenience with timeless style. A rare opportunity to own a stunning home in one of Leonardtown’s most sought-after communities—don’t miss it.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,764
Status:
NEW LISTING
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

Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the community park. Everything is right where you need it in this lovely home. A must see.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,097
Status:
Active
MLS#:
MDSM2029036
Type:
Single Family-Detached
Subdivision:
St Clements Wood
Lot size:
0.19 Acres
Year built:
1966
Courtesy: ListWithFreedom.com 855-456-4945
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ADDITIONAL INFORMATION

Experience refined waterfront living in this completely renovated rancher overlooking Saint Clements Bay. Originally built in 1966, this residence has been thoughtfully reimagined from top to bottom with extensive structural, electrical, and plumbing upgrades, blending modern luxury with effortless coastal charm. Situated on a waterfront lot, the property offers its own private L-shaped pier—perfect for boating, fishing, or simply enjoying peaceful bay views. The pier measures 91’ x 5’ with a 26’ x 10’ extension and approximately 7 feet of water depth to the decking, complete with a pier shed and brand new stairs leading from the home. The open-concept design welcomes you with sweeping water views the moment you step inside, creating a seamless connection between indoor and outdoor living. This home features 4 bedrooms, 2 full bathrooms, and 2 half bathrooms, offering both comfort and versatility. The primary suite serves as a private retreat with two closets and a spa-inspired bathroom featuring an oversized walk-in shower and double-sink vanity. High-end finishes flow throughout, including brand new engineered hardwood flooring in the main living areas, plush carpet in three bedrooms, and porcelain tile in three bathrooms. The designer kitchen is equipped with brand new quartz countertops, a gas stove with vent hood, refrigerator, dishwasher, wine cooler, and a dedicated coffee and wine bar area—ideal for entertaining or everyday enjoyment. Sliding glass doors and expansive windows frame stunning water views and fill the home with natural light. Outdoor living is elevated with a brand new waterfront deck, fresh siding on the sides and rear, a painted brick front, and a new front door, all enhancing curb appeal and durability. Major system updates include a brand new central AC and heating system, brand new gas water heater, an original heat pump serving the den addition, oil heat, and a fully improved crawl space with a new vapor barrier. The roof was replaced in 2009, along with new double-pane vinyl windows that fold in for easy cleaning. Additional highlights include two sheds, ample interior storage, and two on-property parking spaces. An optional, low-annual civic association fee provides access to picnic and swimming areas, boat ramps, and a playground. Conveniently located just an 11-minute drive to Leonardtown Square, offering a vibrant mix of shopping, dining, waterfront parks, historic charm, and year-round community events. This exceptional waterfront property offers a rare opportunity to enjoy modern luxury, private pier access, serene bayfront living, and close proximity to one of Southern Maryland’s town centers.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,700
Status:
Active
MLS#:
MDSM2028922
Type:
Single Family-Detached
Subdivision:
Leonardtown
Lot size:
1.17 Acres
Year built:
1988
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome to 22164 Miller Court, Leonardtown offering exceptional Breton Bay waterfront living with approximately 100 feet of shoreline, a private pier, and both a power boat lift and a manual boat lift, perfect for boating, fishing, kayaking, and enjoying life on the water. From sunrise coffee to sunset evenings overlooking the river, this property delivers true waterfront serenity. This beautifully maintained home features 4 bedrooms and 3 full baths, including a desirable main-level primary bedroom and full bath for comfortable one-level living. Additional bedrooms and baths provide plenty of space for guests, family, or home office needs. Hardwood floors and tile flooring add timeless appeal and durability throughout, while the inviting living area includes a cozy fireplace, perfect for cooler evenings. The kitchen is well-appointed with a propane gas stove, ideal for cooking and entertaining. The dining room opens directly to a screened-in porch, creating a seamless indoor-outdoor flow and a relaxing space to enjoy meals, morning coffee, or evening breezes. Outdoor living truly shines with a fenced-in Gunite pool, perfect for summer entertaining and relaxation. The walk-out basement offers additional living and storage potential and includes a dedicated workshop, ideal for hobbies, projects, or additional storage needs. Additional highlights include a 30-amp transfer panel and switch for added peace of mind, a pool shed, and a separate garden shed. Parking and storage are abundant with a detached two-car garage plus an additional one-car carport, perfect for vehicles, boats, and recreational equipment. A rare opportunity to enjoy comfort, functionality, and the ultimate Breton Bay waterfront lifestyle in a private and peaceful setting.

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
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ADDITIONAL INFORMATION

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. 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:
3
Baths:
4.00
Sq.Ft.:
2,308
Status:
Active
MLS#:
MDSM2028828
Type:
Townhouse
Subdivision:
Clark's Rest Phase 1
Lot size:
0.06 Acres
Year built:
2017
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Beautiful Clark’s Rest townhome offering three finished levels, a two-car garage, and over 2,300 square feet of living space. The main level features hardwood floors, a gourmet kitchen with granite countertops and 42-inch cabinetry, a separate formal dining space, and a large family room—ideal for both everyday living and entertaining. The fully finished lower level includes a spacious recreation room and a full bathroom, perfect for guests, a home office, or additional living space. Upstairs, the expansive primary suite boasts an en-suite bath with a tiled shower, soaking tub, double sinks, and two generous closets. Two additional bedrooms, a full hall bath, and a conveniently located laundry room complete the upper level. Enjoy outdoor living on the large rear deck with a motorized awning, ideal for relaxing or entertaining.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,222
Status:
Active
MLS#:
MDSM2028376
Type:
Single Family-Detached
Subdivision:
Singletree
Lot size:
0.28 Acres
Year built:
2006
Courtesy: Home Towne Real Estate 301-862-4000
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ADDITIONAL INFORMATION

PRICE IMPROVEMENT! Beautiful 2 story home situated on a professionally landscaped level lot with fully fenced back yard. Home is freshly painted and has newly installed carpet throughout main and upper levels. Roof and gutters were recently replaced in 2025. HVAC has been serviced annually. Upper level has 4bedrooms; 2 full bathrooms and laundry room. Main level consists of living room, dining room, family room with propane fireplace, kitchen with pantry and eating area, half bath, direct access to the 2-car garage, and access to backyard. Lower-level basement is accessed from inside and also has 6-foot-wide areaway leading to the level fully fenced backyard. Backyard is accessible from right side via 4-foot gate and on the left side via 8-foot gate Home is located on cul-de-sac with easy short walk to all restaurants and shops in downtown Leonardtown, College of Southern Maryland, Saint Mary's Hospital and Leonardtown wharf. Excellent condition and ready to move-in. Basement currently has numerous weightlifting gear which should not be touched for your safety during all showings. Pictures will be added on 10 or 11 January. Thanks for showing

Beds:
4
Baths:
3.00
Sq.Ft.:
2,500
Status:
Active
MLS#:
MDSM2028700
Type:
Single Family-Detached
Subdivision:
Hawks Nest
Lot size:
1.34 Acres
Year built:
2025
Courtesy: CENTURY 21 New Millennium 443-968-9595
View additional info

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:
3.00
Sq.Ft.:
1,952
Status:
Active
MLS#:
MDSM2028668
Type:
Single Family-Detached
Subdivision:
Breton Bay Pud
Lot size:
0.37 Acres
Year built:
1992
Courtesy: Berkshire Hathaway HomeServices PenFed Realty 410-394-0990
View additional info

ADDITIONAL INFORMATION

A rare opportunity for golf course living! Welcome home to this beautifully appointed colonial, perfectly situated on the 6th hole of the Breton Bay Golf Course. Featuring granite countertops, some new appliances, fresh paint, and more, this home is move-in ready. The upper level offers three spacious bedrooms, with a fourth bedroom located in the finished basement—ideal for guests or a home office. Enjoy breathtaking views of the 5th and 6th holes from the screened-in porch, expansive deck, and private hot tub. Just steps from the neighborhood beach, public golf course and clubhouse, and a private marina with rental slips available, this home delivers the best of the Breton Bay lifestyle. Seller is offering a flooring credit for the first floor with Clarke's Flooring.

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
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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.:
3,482
Status:
Active
MLS#:
MDSM2028424
Type:
Single Family-Detached
Subdivision:
Academy Hills
Lot size:
0.21 Acres
Year built:
2010
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Well-maintained home in desirable Academy Hills, situated on a level corner lot within walking distance to Downtown Leonardtown. This home features an open floor plan with generously sized rooms and abundant natural light from extra windows throughout. The family room offers a cozy gas fireplace and flows seamlessly into the breakfast room and kitchen with breakfast bar, plus a separate formal dining room—perfect for entertaining. The main level includes convenient laundry, spacious bedrooms, and two large full bathrooms. The finished basement expands the living space with a rec room, a fifth bedroom, and a third full bath—ideal for out-of-town guests or extended family. Additional highlights include custom blinds, finished garage walls, a fenced backyard, and a maintenance-free deck with railings. Solar panels add energy efficiency to this move-in-ready home.

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! Back active after brief weather -related pause. Showings now available. 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:
4
Baths:
3.00
Sq.Ft.:
3,372
Status:
Active
MLS#:
MDSM2028350
Type:
Single Family-Detached
Subdivision:
Leonardtown Farms
Lot size:
1.08 Acres
Year built:
2010
Courtesy: EXP Realty, LLC 888-860-7369
View additional info

ADDITIONAL INFORMATION

Stunning Dunleigh model by Marrick Homes, tucked away at the end of a quiet cul-de-sac on over 1 full acre in desirable Leonardtown Farm! Offering nearly 3,400 sq ft of finished living space, this beautifully maintained 4BR/2.5BA home features a spacious, gourmet kitchen with large center island, upgraded cabinets and granite countertops, and stainless steel appliances – perfect for entertaining. Enjoy formal living and dining rooms, plus a comfortable family room with fireplace just off the kitchen. A private office/study on the main level is ideal for remote work or flex space. The full, unfinished basement provides endless potential for future expansion and/or storage. Step outside to a beautiful backyard featuring a stamped concrete patio and pergola - perfect for outdoor entertaining and relaxation. Additional highlights include a 3-car garage, charming covered, wrap around front porch, and generous room sizes throughout. Conveniently located in Leonardtown! Close to restaurants, shopping, schools, and NAS Pax River. A must-see home!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,764
Status:
Active
MLS#:
MDSM2028512
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

Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the community park. Everything is right where you need it in this lovely home. A must see.

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

Rare Multigenerational Home in Breton Bay – Two Homes in One! Experience the perfect blend of contemporary design and flexibility in the highly sought-after Breton Bay community. This sprawling 3,464 sq. ft. residence has been thoughtfully reimagined to offer two distinct living experiences under one roof—perfect for multigenerational families, a premium home office suite, or a high-end guest wing. The Main Residence is light, airy, and modern. Step into the main level featuring with hardwoods, vaulted ceilings, and an open-concept living and dining area anchored by a cozy fireplace. The "cottage-core" gourmet kitchen is a chef’s delight with custom cabinetry and a charming storage closet the owner's have used for wine storage. The entire top level is the owner's sanctuary as a private retreat featuring an ensuite bath, deep walk-in closet, and an architectural overlook that captures the home’s unique character. You'll have room to breathe with the two additional spacious bedrooms and a full bath that occupy their own dedicated level, providing perfect separation for children or guests. The guest suite / secondary residence allows for absolute privacy. With its own private exterior entrance, this fully equipped 2-bedroom, 1-bath wing is far more than an "apartment." It features its own kitchen, living area with a private deck, and dedicated laundry. Whether it’s for long-term family stay or a premium rental, the versatility is unmatched. There is also value-added peace of mind as the owner's installed a brand new septic system in the fall 2025, which save tens of thousands in future costs. The owner's have freshly updated the home and guest suite / secondary residence with new carpet and paint throughout most of the home and secondary residence. Enjoy access to the community beach, pier, and playground just moments away. There is also a beautiful golf course available to homeowners for an additional membership fee. This isn't just a house; it's a solution for the modern family. Ditch the cramped quarters and discover the space, privacy, and community you’ve been searching for. Schedule your private tour today—homes with this much versatility are a rare find!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,075
Status:
Active
MLS#:
MDSM2028504
Type:
Single Family-Detached
Subdivision:
Wilderness Run
Lot size:
0.99 Acres
Year built:
2001
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

Nestled on a beautifully maintained 1 acre lot, this 5 bedroom, 3.5 bathroom home is conveniently located in Leonardtown's Wilderness Run community. A welcoming foyer leads to a formal dining room and a charming country style kitchen which opens to a spacious family room. The kitchen features space for a table, a large pantry, stainless steel appliances, granite countertops, and direct access to the expansive rear deck overlooking the large private backyard with firepit area and mature trees adding natural privacy. The door off the family room leads to a cozy nook, great for drinking your morning coffee as you watch the birds and abundant wildlife. A convenient flex room off the foyer is perfect for a home office or quiet sitting room. Upstairs, the large primary suite has an en suite bathroom with soaking tub and a generous walk-in closet. Three additional bedrooms are comfortably sized with nice closets. The second floor has a laundry area for everyday convenience. The fully finished basement provides exceptional versatility. It includes a well-appointed kitchenette with abundant cabinetry and granite countertops with subway tile backsplash. A large recreation room with built-ins gives plenty of room for entertaining. A full bath has dual access points for the additional bedroom, office or home gym. This room is complete with a generous closet and stackable washer and dryer and multiple windows for natural light and an exterior ground level exit door. The basement also has a large storage area with shelving to complete the lower level. The neighborhood is located within minutes of Downtown Leonardtown with restaurants, shopping, nightlife, the winery, and seasonal events. The wharf offers a boardwalk, playground, and beautiful water views.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,500
Status:
Active
MLS#:
MDSM2028220
Type:
Single Family-Detached
Subdivision:
Hawks Nest
Lot size:
1.34 Acres
Year built:
2025
Courtesy: CENTURY 21 New Millennium 443-968-9595
View additional info

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:
3
Baths:
2.00
Sq.Ft.:
1,732
Status:
Active
MLS#:
MDSM2028348
Type:
Single Family-Detached
Subdivision:
Chestnut Ridge
Lot size:
2.43 Acres
Year built:
1991
Courtesy: O'Brien Realty ERA Powered 301-863-2400
View additional info

ADDITIONAL INFORMATION

Welcome to this charming single-family rambler nestled in the peaceful Chestnut Ridge subdivision, and only a short drive to downtown Leonardtown. This home blends convenience, comfort, accessibility, and serene country living. Step inside to a spacious, open floor plan with a kitchen perfect for gathering and everyday living. Next to the kitchen is a formal dining room with beautiful wood floors that flow throughout, adding warmth and character to the home. Thoughtfully designed for accessibility , the property features exterior ramps leading to the garage, patio, and deck, as well as an accessible primary suite complete with level flooring, properly placed handrails, and a generously sized walk-in closet. The primary bedroom also includes a sliding glass door that opens onto a partial wrap-around deck, offering peaceful views of the backyard. Outside, enjoy the freedom and space of your 2.43-acre lot, featuring a large two-car garage, storage shed, generator, and a propane tank. Warm, inviting, and thoughtfully updated for comfort—this property is ready to welcome you home. Offer deadline by Saturday 12/13/2025

Beds:
4
Baths:
4.00
Sq.Ft.:
3,736
Status:
Active
MLS#:
MDSM2028276
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2009
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome to 23581 Gallent Fox Way, a beautifully maintained and thoughtfully upgraded home nestled in the heart of highly desirable Leonard’s Grant. Situated in one of Leonardtown’s most sought-after communities, this 4-bedroom, 3.5-bath 3,933 sq ft residence combines comfort, convenience, and a true sense of community living. Perfectly positioned directly across from the community pool and recreation center and adjacent to the neighborhood Green, this location offers stunning views and unmatched access to neighborhood amenities right outside your front door. Step inside to find a warm, inviting layout enhanced by a recently renovated kitchen featuring modern finishes, ample cabinetry, and a spacious center island ideal for cooking, gathering, and entertaining. The kitchen flows seamlessly into the bright, open living and dining spaces, creating the perfect environment for everyday living. Upstairs, the home boasts generously sized bedrooms including a convenient Jack & Jill bathroom designed for shared use while maintaining privacy. The luxurious primary suite is a peaceful retreat with a spacious layout and a spa-inspired ensuite that showcases the signature QBH upgraded shower, an exceptional highlight providing a truly relaxing experience. The fully finished basement expands your living space and offers endless possibilities, featuring a full bathroom, additional bedroom, and walk-up access to the backyard. Movie and game nights become unforgettable with the included projector and built-in sound system, creating a true home theater experience. Outdoor living is an absolute dream in the fenced backyard, complete with a beautifully designed paver patio, built-in fire pit, and covered porch for shade and comfort, perfect for quiet evenings at home or hosting friends and family. Leonard’s Grant is known for its friendly atmosphere, community amenities, and prime location just minutes from top-rated schools, Historic Downtown Leonardtown, restaurants, shopping, and Pax River NAS. Enjoy miles of sidewalks, playgrounds, sports courts, fields, and seasonal community events that bring neighbors together. This exceptional property offers the full package, modern upgrades, a functional layout, community lifestyle, and a premium location. Come experience why Leonard’s Grant is one of Southern Maryland’s premier places to call home!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,594
Status:
Active
MLS#:
MDSM2028218
Type:
Single Family-Detached
Subdivision:
Chestnut Ridge
Lot size:
2 Acres
Year built:
1994
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

Nestled within one of the most desirable subdivisions, this classic two-story Colonial welcomes you home with charm and a sense of privacy on two wooded acres. Quality construction throughout from the sunroom to the kitchen remodel you will see the workmanship! Once inside you will feel the warmth of meticulously cared-for details : gleaming hardwood floors through the main level, a spacious separate dining room into a beautifully updated kitchen. Corian countertops, stainless steel appliances, and center island make it a joy to cook and gather Kitchen opens into a cozy family room anchored by a wood-burning fireplace and a light-filled sunroom with lots of windows inviting the outside in. Connecting deck overlooking your own peaceful woods Upstairs, four generous bedrooms offer restful retreats, including a primary suite with an en-suite bath featuring dual vanities, a soothing soaking tub, a separate shower, and a spacious walk-in closet. Practical touches complete the picture: an oversized two-car garage for all your toys and storage, plus a charming large Amish-built shed Bonus! Encapsulated crawlspace w/ commercial grade dehumidifier, sprinkler system, heat pump 2024, new roof 2016

Beds:
4
Baths:
3.00
Sq.Ft.:
2,262
Status:
Active
MLS#:
MDSM2027210
Type:
Single Family-Detached
Subdivision:
Jordan At Singletree
Lot size:
0.26 Acres
Year built:
2002
Courtesy: JPAR Real Estate Professionals 301-684-4895
View additional info

ADDITIONAL INFORMATION

Welcome home to 41535 Singletree Dr. This beautiful colonial offers 4 bedrooms and 2.5 baths with laminate hardwood floors throughout the first level. New carpet has been installed throughout the second level. The kitchen features quartz countertops and opens to a living room with a cozy gas fireplace, as well as a formal dining room and sitting area, perfect for gatherings and everyday living. Upstairs, you’ll find four spacious bedrooms, while outside, a level lot and deck provide space for cooking out and private entertaining. Located within walking distance to Leonardtown’s shops, restaurants, waterfront, and hospital, and served by sought-after Leonardtown schools. This property also has a 2.25% assumable VA mortgage, offering qualified buyers a valuable opportunity to secure exceptional financing terms in today’s market.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,586
Status:
Active
MLS#:
MDSM2027532
Type:
Single Family-Detached
Subdivision:
Little Woods
Lot size:
2.1 Acres
Year built:
1954
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

Waterfront Retreat with Spectacular Sunsets Waterfront Retreat with Spectacular Sunsets. Welcome to your dream waterfront retreat! This charming 4-bedroom, 2-bath home is perfectly situated on 2.1 quiet acres with no HOA, offering the peace and privacy you’ve been looking for. Step inside to find large windows that frame breathtaking water views and allow natural light to fill the spacious living room, dining room, kitchen, and family room. A large screened-in porch invites you to relax and take in the fresh breezes while watching the spectacular sunsets over the water. Enjoy waterfront living with your very own private pier, ideal for boating, fishing, or simply unwinding by the shore. A oversized garage and separate work shed adds extra convenience for parking, storage or hobbies. This property combines the best of comfort, natural beauty, and tranquility—perfect for year-round living or a weekend escape.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,500
Status:
Active
MLS#:
MDSM2028266
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.22 Acres
Year built:
2010
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality. The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your morning coffee in peace. The main-level primary suite features a sitting area and a large bathroom with dual vanities, offering a private retreat from the rest of the home. Upstairs, you’ll find a versatile loft area and three generously sized bedrooms. The fully finished basement adds even more living space, complete with a large rec room and an additional bedroom and unfinished storage. Enjoy all the amenities Leonard’s Grant has to offer, just steps away from the community pool, tennis courts, and more!

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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

    $510,000
    12.7%
    change since last quarter
  • # Active listings

    91
    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