Leonardtown MD Real Estate & Homes for Sale

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Beds:
5
Baths:
4.00
Sq.Ft.:
5,484
Status:
Active
MLS#:
MDSM2033428
Type:
Single Family-Detached
Subdivision:
AVENMAR
Lot size:
2.19 Acres
Year built:
2002
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome to Avenmar, where this spacious home is situated on a beautiful lot of over two acres, offering privacy, mature trees, and a peaceful wooded setting. Built in 2002 and largely in its original condition, the home has been well maintained and is ready for its next owner to bring their own style and updates. The main level offers a spacious, open layout with a formal dining room, formal living room, private office, and full bath. The centerpiece of the home is the impressive two-story family room with a gas fireplace and floor-to-ceiling windows overlooking the trees and woods. The kitchen features Corian countertops, solid hardwood cabinetry, generous workspace, and an easy flow into the main living areas. Upstairs, front and rear staircases lead to a catwalk overlooking the family room below. The primary ensuite features a private bath and two generous walk-in closets. Three additional large bedrooms, a full bath, and convenient upper-level laundry complete this level. The fully finished walk-out lower level provides even more living space with a large recreation room, fifth bedroom, and full bath, making it ideal for guests, extended family, a home gym, or additional entertaining space. Avenmar offers an exceptional collection of community amenities, including access to Breton Bay with a community pier and kayak launch, clubhouse, swimming pool, tennis and volleyball courts, walking trails, horse stables, and equestrian trails. With over two acres, a private wooded setting, three finished levels, five bedrooms, multiple living and entertaining spaces, and access to Breton Bay, this property offers a great opportunity to update and personalize a substantial home in one of Leonardtown's most distinctive communities.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,793
Status:
Active
MLS#:
MDSM2033246
Type:
Single Family-Detached
Subdivision:
CLARK'S REST
Lot size:
0.16 Acres
Year built:
2023
Courtesy: The Southside Group Real Estate 301-298-2892
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ADDITIONAL INFORMATION

OPEN HOUSE CANCELLED The scheduled open house has been cancelled. Welcome to 41524 Fairwood Ct, Leonardtown, MD 20650! This inviting ranch-style home offers comfortable one-level living with a spacious, open-concept great room, dining area, and kitchen designed for everyday living and entertaining. The kitchen features a generous island and built-in pantry, while the convenient mudroom and first-floor laundry add functionality. The thoughtful layout includes two bedrooms with a shared bath, plus a private owner’s suite featuring a spa-like shower and walk-in closet. The finished partial basement provides additional living space with a recreation room, full bath, and bedroom—perfect for guests, a home office, or additional entertaining space. A versatile floor plan, spacious living areas, and convenient features make this home a wonderful place to call home!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,774
Status:
Active
MLS#:
MDSM2033354
Type:
Single Family-Detached
Subdivision:
VILLAGES AT LEONARDTOWN
Lot size:
0.29 Acres
Year built:
2004
Courtesy: Baldus Real Estate, Inc. 301-934-8407
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ADDITIONAL INFORMATION

Discover a prime investment opportunity in the charming VILLAGES AT LEONARDTOWN! This 4-bedroom, 2.5-bath Colonial home, built in 2004, boasts 2,774 sq. ft. of potential. With a spacious unfinished basement featuring walkout stairs and rough bath plumbing, you have the perfect canvas to create additional living space or rental units, maximizing your return on investment. The property sits on a generous 0.29-acre lot, offering ample outdoor space for future enhancements or landscaping. The attached 2-car garage and driveway provide convenience for tenants or future buyers. Located in a desirable community, this home is poised for appreciation, making it an ideal addition to your portfolio a solid structure of brick and vinyl siding, upkeep is minimal, allowing for a hassle-free investment. Seize this chance to invest in a property that combines comfort, potential, and value in a thriving neighborhood!

Beds:
5
Baths:
3.00
Sq.Ft.:
2,601
Status:
Active
MLS#:
MDSM2033166
Type:
Single Family-Detached
Subdivision:
AVENMAR
Lot size:
3.21 Acres
Year built:
2002
Courtesy: Metro City Realty 240-993-9888
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ADDITIONAL INFORMATION

Welcome to this beautiful brick-front retreat in the highly sought-after Avenmar Community of historic Leonardtown, Maryland. Set on over 3 private acres and tucked away on a secluded lane shared by only three other homes, this property offers the perfect blend of privacy, nature, and convenience, an ideal setting for cozy fall evenings and peaceful year-round living. Freshly updated with a new roof, new carpet throughout, and fresh paint, this move-in-ready home features 4 bedrooms, 2.5 bathrooms, and an abundance of charm. The spacious primary suite is a true sanctuary, complete with its own fireplace, a large walk-in closet, and an impressive ensuite bath with a Jacuzzi tub, perfect for unwinding as the weather cools. A second fireplace in the family room creates a warm, inviting gathering space for autumn nights with family and friends. The main level includes a dedicated office/den, a convenient half bath, and easy access to the expansive rear deck overlooking the private backyard, ideal for fall entertaining, morning coffee, or watching the leaves change. The upper-level laundry room includes a washer and dryer, and the unfinished walk-out basement offers endless potential for future expansion, recreation, or storage. Additional highlights include a 2-car garage, mature landscaping with unique banana and bamboo plants, and a serene setting perfect for nature lovers. Beyond the home, Avenmar offers an exceptional lifestyle with exclusive resident amenities, including: Community pool with lifeguards and swim lessons Tennis courts Horse stables Private water access to Breton Bay Community pier Canoe storage and canoe use Playgrounds Clubhouse and waterfront guest room rentals Community events and activities Convenient directory of babysitters and pet sitters Despite its tranquil setting, the home is just minutes from schools, shopping, dining, and local attractions, with an easy commute to Patuxent River Naval Air Station (PAX River). This is a rare opportunity to own a private estate in one of Southern Maryland’s most desirable waterfront communities, your perfect place to settle in for the season and stay for a lifetime.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,562
Status:
Active
MLS#:
MDSM2033146
Type:
Single Family-Detached
Subdivision:
BRETON BAY
Lot size:
0.43 Acres
Year built:
1992
Courtesy: Infinitas Realty Group 240-925-2224
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ADDITIONAL INFORMATION

Welcome to 40611 Merion Court, Leonardtown, MD 20650! This stunning three-level Colonial offers the perfect blend of elegance, comfort, and resort-style living, ideally positioned with beautiful views backing directly to Breton Bay golf course. Featuring 4 bedrooms, 3.5 baths, and a fully finished basement, this home provides exceptional space for both everyday living and entertaining. The finished lower level includes a dedicated home theater and private office, while the screened-in back porch creates a wonderful outdoor retreat overlooking the manicured fairway and mature landscaping. Inside, you'll find a spacious and inviting layout designed for comfortable living, while the beautifully landscaped grounds provide privacy and a picturesque setting. The spacious primary suite is a true retreat, complete with a vaulted ceiling, private sitting room, generous walk-in closet, and a completely remodeled primary bathroom- showcasing gorgeous stonework and high-end finishes. Located in a sought-after community offering an impressive array of amenities, residents can enjoy access to a private pier, golf course, and swimming pool—bringing a vacation-like atmosphere right to your doorstep. Whether you're relaxing on the back porch, enjoying movie night in your private theater, working from home, or taking advantage of the community amenities, 40611 Merion Court offers the lifestyle you've been waiting for!

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2033226
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

***ALMOST READY****Builder Incentive $17,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #143 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, black fixtures, white perimeter kitchen cabinets, 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 W/D on 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. Visit the Meadows at Town Run II model home to explore available floor plans and new construction opportunities. Model home hours are Thursday–Sunday, 11 AM–4 PM. Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,388
Status:
Active
MLS#:
MDSM2032802
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
3.8 Acres
Year built:
2017
Courtesy: RMG Realty 540-709-1011
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ADDITIONAL INFORMATION

Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2017, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers four well-appointed bedrooms, including a convenient entry-level bedroom, perfect for guests or those seeking single-level living. The primary suite features a walk-in closet and a spa-like bathroom complete with a soaking tub and a walk-in shower, providing a serene retreat at the end of the day. Additional interior highlights include plush carpeting, elegant hardwood floors, and ceiling fans that enhance comfort throughout the seasons. For those who appreciate technology, the home is equipped with a sound system, ensuring that your favorite tunes accompany you in every room. Outside, the property features a screened in porch, perfect for outdoor relaxation while enjoying the tranquility of your surroundings. The oversized detached garage offers ample space for vehicles and storage and has heat/ac, electricity and plumbing while complemented by a paved driveway for easy access. There is ample parking space for vehicles, campers, and more! Enjoy the peace of country living while being just a short drive from local amenities, shopping, and dining options. Don't miss the opportunity to make this beautiful residence your forever home!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,834
Status:
Active
MLS#:
MDSM2032956
Type:
Single Family-Detached
Subdivision:
HERRING CREEK ESTATES
Lot size:
0.84 Acres
Year built:
1970
Courtesy: CENTURY 21 New Millennium 301-609-9000
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ADDITIONAL INFORMATION

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

Beds:
5
Baths:
2.00
Sq.Ft.:
1,552
Status:
Active
MLS#:
MDSM2032950
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
4.12 Acres
Year built:
1986
Courtesy: Samson Properties 703-378-8810
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ADDITIONAL INFORMATION

All forms of financing are available for this property. Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road in Leonardtown, Maryland. Situated on more than four acres, this spacious five-bedroom, manufactered two-bath rambler offers a rare combination of comfortable one-level living, privacy and future possibilities. he generous homesite provides abundant room for outdoor recreation, gardening, equipment storage, animals or creating your own private retreat. The property may also appeal to builders, investors or buyers exploring potential subdivision or development opportunities, subject to county zoning, approvals, utilities and feasibility studies. Inside, the home offers a flexible five-bedroom layout with space for home offices, guest rooms, multigenerational living or hobby areas. Its rambler-style design provides convenient everyday living with minimal stairs. Located near historic Leonardtown, local shopping, dining, schools, medical facilities and Southern Maryland commuter routes, this property is ideal for buyers seeking acreage without sacrificing access to nearby amenities. Bring your vision and discover the potential of this distinctive Leonardtown property.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,730
Status:
Active
MLS#:
MDSM2032698
Type:
Single Family-Detached
Subdivision:
BRETON BAY/SOCIETY HILL
Lot size:
0.56 Acres
Year built:
1972
Courtesy: Compass 703-229-8935
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ADDITIONAL INFORMATION

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

Beds:
5
Baths:
4.00
Sq.Ft.:
4,346
Status:
Active
MLS#:
MDSM2032660
Type:
Single Family-Detached
Subdivision:
VILLAGES AT LEONARDTOWN
Lot size:
0.35 Acres
Year built:
2005
Courtesy: Coldwell Banker Premier 301-645-1700
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ADDITIONAL INFORMATION

Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so much more just inside the walls! Outside the walls of the home, features a shed, fenced in backyard, a beautifully manicured lawn watered by an in-ground irrigation system and several flower beds for all a plant enthusiast could ever ask for! Situated in the subdivision known as The Villages at Leonardtown, we are only minutes from all the shops, dining, and attractions Leonardtown has to offer, with a further drive to all the shops, attractions, dining near Pax River Naval Base and the surrounding area offers. Come take a look at this home today!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,691
Status:
Active
MLS#:
MDSM2032426
Type:
Single Family-Detached
Subdivision:
LANEDON
Lot size:
0.46 Acres
Year built:
2005
Courtesy: Keller Williams Flagship 410-729-7700
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ADDITIONAL INFORMATION

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

Beds:
4
Baths:
4.00
Sq.Ft.:
3,314
Status:
Active
MLS#:
MDSM2031988
Type:
Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.16 Acres
Year built:
2012
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside. The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant cabinetry, a spacious walk-in pantry, and a convenient mudroom just off the rear-entry garage. Adding to the home’s incredible value are solar panels, allowing the current owners to enjoy a minimal electric bill—an exceptional benefit that provides long-term energy savings. Step outside to your fully fenced backyard, where you’ll find an expansive paver patio designed for relaxing and entertaining. Gather around the built-in fire pit, host summer cookouts, or simply unwind in your own private outdoor retreat. Located in one of Leonardtown’s most desirable neighborhoods, Leonard’s Grant offers outstanding community amenities, including a pool, clubhouse, playgrounds, walking trails, tennis and basketball courts, all just minutes from downtown Leonardtown, restaurants, shopping, and not far from NAS Patuxent River. Move-in ready, energy-efficient, and perfectly located, this home offers the ideal combination of comfort

Beds:
4
Baths:
4.00
Sq.Ft.:
3,690
Status:
Active
MLS#:
MDSM2032140
Type:
Single Family-Detached
Subdivision:
CLARK'S REST PHASE 2
Lot size:
0.15 Acres
Year built:
2020
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

Charming Home in Prime Leonardtown Location This inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops. Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining room connects through a butler’s pantry to a full walk-in pantry and flows into a modern kitchen featuring granite counters, upgraded cabinetry, stylish subway tile backsplash, large center island, gas cooktop, double wall ovens, and a premium Samsung Bespoke 4-drawer refrigerator with beverage center. The kitchen flows to an eat-in area and a cozy family room with gas fireplace flanked by beautiful custom built-ins. A powder room completes the main level. Luxury vinyl plank flooring runs throughout the main level and upstairs hallway, with hardwood stairs. Upstairs, the spacious primary suite includes a deluxe bathroom with dual sinks, soaking tub, ceramic-tiled shower, and a large walk-in closet. Three additional generous bedrooms, another full bath, and a sizable laundry room round out the upper level. The finished lower level offers a flex room, family room, full bath, and excellent storage. Outside, enjoy a composite deck, fully fenced yard, and firepit — perfect for relaxing or entertaining. Additional highlights include a 2-car garage and owned solar panels that keep utility bills impressively low.and low maintenance yard! Enjoy resort-style living with neighborhood amenities including a spacious clubhouse, a 3,500 sq ft pool with separate kiddie pool, tennis and basketball courts, playground, and walking trails. Ideal location, thoughtful layout, and move-in ready condition — this home checks every box.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,834
Status:
Active
MLS#:
MDSM2031832
Type:
Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.24 Acres
Year built:
2010
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

VA LOAN MAY BE ASSUMABLE AT 4.375% BY A QUALIFIED BUYER, SUBJECT TO VA APPROVAL. Welcome to this exceptional home in the sought-after Leonard’s Grant community, where timeless design, quality finishes, and incredible indoor and outdoor living come together. From the inviting front porch to the private, tree-lined backyard, every space has been thoughtfully designed for comfortable living and effortless entertaining. Inside, stunning Tigerwood floors flow throughout much of the home, creating warmth and elegance. The main level features a private office, a spacious formal dining room, and a gourmet kitchen with abundant cabinetry, generous workspace, and a large walk-in pantry. The kitchen opens seamlessly to the bright, welcoming great room, while the spectacular sunroom is filled with natural light and overlooks the peaceful backyard. Step outside to the composite deck, which leads to a beautiful covered patio, offering multiple outdoor living spaces to relax, entertain, and enjoy the fenced backyard with 4-year old 10x12 shed that backs to mature trees. Convenience continues with a main-level laundry room located just off the kitchen. Upstairs, the luxurious primary suite is a true retreat, complete with a spacious sitting area, an enormous walk-in closet, and a spa-inspired bath featuring a soaking tub and an oversized walk-in shower. Three additional bedrooms are located on the upper level, including a private guest suite with its own attached bathroom. The upper-level landing, accented by beautiful wood flooring, adds to the home’s open and elegant feel. The finished walk-out basement features rare 9-ft ceilings and expands your living space with a large fifth bedroom, full bath, theater room, recreation room, and a wet bar—perfect for movie nights, entertaining, or hosting overnight guests. Walk directly out to the patio and enjoy the privacy of the backyard. Call for an appointment today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,976
Status:
Active
MLS#:
MDSM2032286
Type:
Single Family-Detached
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.23 Acres
Year built:
2026
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
3.00
Sq.Ft.:
2,701
Status:
Active
MLS#:
MDSM2032276
Type:
Single Family-Detached
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.23 Acres
Year built:
2026
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes’ Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow. The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner’s suite includes generous closet space and a private bath, with three additional bedrooms, a full bath, and convenient second-floor laundry. Estimated delivery 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers use QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about Homesite 4, available selections, incentives, and delivery timing. Meadows at Town Run II is located in Leonardtown with convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. This section will include only 12 single-family homes. Planned community amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Former decorated Mattingly model shown for example purposes only. Photos do not represent the actual home on Lot 4. Actual home, features, finishes, options, selections, and pricing may vary.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,072
Status:
Active
MLS#:
MDSM2032268
Type:
Single Family-Detached
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.28 Acres
Year built:
2026
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes’ Fenwick Model ... a beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing. The Fenwick offers a smart, comfortable layout with a spacious family room, kitchen and breakfast area, 9-foot ceilings, granite/quartz countertops, 42-inch cabinets, stainless steel appliances, and Quality Built Homes’ signature craftsmanship throughout. Upstairs, the primary suite features a private en suite bath with dual vanities, soaking tub, and QBHI’s Deluxe Shower. Two additional bedrooms, a full bath, and second-floor laundry complete the upper level. Meadows at Town Run II is one of Leonardtown’s newest opportunities, with only 12 single-family homes planned in this section. Planned amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Estimated delivery 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers choose QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II in Leonardtown is open Thursday through Sunday from 11 AM to 3 PM. Schedule your appointment today. Photos shown are of a previous Fenwick model home and are provided as an example of what can be built. Actual home, features, finishes, options, upgrades, selections, and layout may vary.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,667
Status:
Active
MLS#:
MDSM2032014
Type:
Single Family-Detached
Subdivision:
MCKAYS BEACH
Lot size:
0.34 Acres
Year built:
1948
Courtesy: RE/MAX One 443-295-6123
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ADDITIONAL INFORMATION

This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal retreat. Nestled on the serene shores of McKays Cove, several major exterior capital improvements are already complete. The structure features a brand-new Amish-built roof, new gutters, and premium new Andersen windows throughout. Personal Boat Ramp: Private ramp for seamless watercraft launching and only one in the community. Private Pier: Sturdy, deep-water access steps from your back door. New Rip Rap: Fresh shoreline reinforcement ensures long-term erosion protection. Large propane tank which is almost full for newly installed gas log fireplace & furnace. All supporting floor beams in the crawl space have been addressed. Blank Canvas Interior: Down-to-the-studs flexibility ready for your custom layout. Generous Footprint: Over 1,600 square feet of customizable living space facing a waterfront picturesque view. This home will be perfect for the generational waterman looking to be in the Potomac River within just a few minutes or the city resident who is looking to escape for the weekend. Several homes on the street have had a complete overhaul and the home next door is just about completed. Now is your turn to create your waterfront dream!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,072
Status:
Active
MLS#:
MDSM2031392
Type:
Single Family-Detached
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.28 Acres
Year built:
2026
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Built Homes’ Clarke Model ... a beautifully designed single-family home offering spacious living, timeless curb appeal, located on a corner lot and the opportunity to personalize your new home from the start. This thoughtfully planned home features 4 bedrooms, 2.5 baths, a rear-entry garage, and an inviting layout designed for everyday living and entertaining. The main level offers a spacious family room that flows seamlessly into the kitchen and breakfast area, along with a formal dining room and living room for added flexibility. Upstairs, the primary suite includes generous closet space and a private en suite bath. Three additional bedrooms, a full bath, and convenient second-floor laundry complete the upper level. Located in the desirable Meadows at Town Run II community in Leonardtown, this homesite offers convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Now is the perfect time to get in early! Buyers may still have the opportunity to select interior options, finishes, and personal selections depending on timing and construction milestones. Estimated delivery for for 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers choose to work with QBHI’s preferred lender and one of their trusted title companies. Quality Built Homes, Inc.’s model home at Meadows at Town Run II in Leonardtown is open Thursday through Sunday from 11 AM to 3 PM. Schedule an appointment today to learn more about building in Meadows at Town Run II. ***Please note***Photos are of a previously built Clarke model home and are shown for illustrative purposes only. Photos do not represent the actual home on Lot 7. Actual home, features, finishes, colors, selections, landscaping, furnishings, and options may vary. Some items shown may be upgrades and are not included in the base price.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,051
Status:
Active
MLS#:
MDSM2031892
Type:
Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.2 Acres
Year built:
2011
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment. Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining room and kitchen. The spacious gourmet kitchen offers double ovens, ample cabinetry, and an eat-in area that opens to the comfortable great room with a gas fireplace. The main level also includes a powder room and a convenient laundry room that doubles as a mudroom just off the garage. Upstairs, the generous primary suite features a large bedroom, a private bath with a corner soaking tub and oversized shower, and plenty of space to relax. Three additional bedrooms complete the upper level. The finished basement provides additional living space, including a fifth bedroom, along with abundant unfinished storage space. With no carpet anywhere in the home, this property offers easy maintenance and a clean, updated feel.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,993
Status:
Active
MLS#:
MDSM2032002
Type:
Single Family-Detached
Subdivision:
ROSEBANK
Lot size:
3.88 Acres
Year built:
1940
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare opportunity to own a private waterfront oasis with an expansive shoreline along both Breton Bay and Combs Creek, extending all the way to the point of its sandy beach peninsula. Enhanced riprap protection, extensive landscaping, and mature surroundings create a truly unforgettable setting. Enjoy 1,545 feet of bay-front water life. Kayakers, yachters, dolphin enthusiasts, fishers, crabbers, and star-gazers are just a few who may find interest in this exemplary waterfront gem. The centerpiece of the outdoor living experience is the spectacular saltwater pool, thoughtfully designed for both relaxation and entertaining. The saltwater pool is finished with premium Wet Edge Premier Stone and Artistic Paver tiles, (featuring embedded seashells sourced from Miami). The tanning ledge measures approximately 8x16' providing the perfect place to lounge and enjoy waterfront views, while a diving board adds to the fun. A dedicated pool pump house and separate dual pool storage unit with its own half bath supports the pool operation. Water enthusiasts will appreciate the exceptional marine amenities. Walking down the hill from the residence leads to a private boathouse and pier system designed with serious boaters in mind. The pier features new stringers, updated power and water service, two slips including the boathouse, and one open slip, a fish cleaning station, and kayak launch area. Low water depth at the end of the pier averages approximately eight feet, making this deep-water location highly desirable for larger vessels and year-round boating. The boathouse, along with the pier, pool house, and detached garage, are all serviced through a dedicated electrical panel system. Water is also available on the pier. Inside, the home has undergone substantial improvements over the years, including a complete transformation of the kitchen and dining areas, creating a stunning gourmet gathering space that serves as the heart of the home. Updated Andersen windows, updated flooring, fresh interior paint, and a beautifully finished laundry and utility room further enhance the home’s appeal. The impressive enclosed sunroom, encompassing approximately 440 square feet, offers year-round enjoyment and flexible living space while showcasing the property’s incredible waterfront views in all seasons. Additional improvements include HardiePlank fiber cement siding, a whole-house generator capable of operating the kitchen and well systems during outages, and a detached 2.5-car garage with a raised floor to improve site grading. The garage offers exceptional storage and future potential for additional finished space should a buyer desire to build up. The well is approximately eight years old. When drilled, the well and pump were upgraded to provide for the additional water needs of the pool, pier and future lawn irrigation. The laundry and utility area features a Navien boiler installed in 2016, providing domestic hot water as well as support for the home’s heating systems. For added value and future convenience, the sellers are in the process of connecting the property to public sewer, which is available within the property. We cannot wait for you to come see the lifestyle that Combs Creek Way has to offer you.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,948
Status:
Active
MLS#:
MDSM2031836
Type:
Single Family-Detached
Subdivision:
VILLAGES AT LEONARDTOWN
Lot size:
0.51 Acres
Year built:
2005
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

There's still time. Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath Colonial offers nearly 3,000 square feet of living space on a beautifully maintained 0.51-acre lot, combining comfortable everyday living with plenty of room to grow. Step inside to a bright, inviting interior featuring new carpet and luxury vinyl plank flooring, giving the home a fresh, move-in-ready feel. The generous floor plan offers plenty of space for relaxing, entertaining, and working from home. The family room provides a warm and welcoming gathering space with a cozy pellet stove, perfect for enjoying cooler evenings. Upstairs, four generously sized bedrooms provide room for family, guests, hobbies, or a home office. The spacious primary suite features a private bath and ample closet space, creating a comfortable retreat at the end of the day. The unfinished basement adds valuable future potential and is ready to become whatever best fits your lifestyle—recreation room, home gym, workshop, office, additional living space, or abundant storage. A bathroom rough-in and grinder pump cutout are already in place, providing a head start for future finishing and an additional bathroom. Step outside and enjoy the privacy of the fully fenced backyard with a 6-foot privacy fence. There's room for pets, play, gardening, outdoor entertaining, or simply relaxing in your own private space. The attached two-car garage provides convenient parking and additional storage. Additional updates include a professionally installed radon mitigation system, providing added peace of mind. Conveniently located just minutes from downtown Leonardtown, shopping, dining, schools, and commuter routes, this home offers the space and flexibility today's buyers are looking for while providing plenty of opportunity to make it your own. Motivated sellers invite you to BRING YOUR OFFER! Reasonable offers will be thoughtfully considered. With nearly 3,000 square feet, a private half-acre lot, four bedrooms, a two-car garage, and tremendous basement potential, this is an opportunity worth seeing in person. Some photos have been virtually staged to illustrate the home's possibilities. It's not too late to make this YOUR home!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,097
Status:
Active
MLS#:
MDSM2031732
Type:
Single Family-Detached
Subdivision:
ST CLEMENTS WOOD
Lot size:
0.19 Acres
Year built:
1966
Courtesy: Allfirst Realty, Inc. 443-320-1344
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ADDITIONAL INFORMATION

Experience waterfront living at its finest in this beautifully renovated home overlooking Saint Clements Bay. Designed to maximize the breathtaking water views, this light-filled home features an open-concept floor plan that seamlessly blends comfortable everyday living with exceptional entertaining space. Offering 4 bedrooms, 2 full baths, and 2 half baths, the home has been extensively renovated from top to bottom with quality craftsmanship and modern coastal finishes. Expansive windows showcase stunning bay views throughout much of the home, while the spacious waterfront deck and extensive waterside patio create the perfect setting for outdoor dining, entertaining, or simply relaxing while enjoying the scenery. The private L-shaped pier provides direct access to boating, fishing, kayaking, paddleboarding, and all the recreational opportunities waterfront living has to offer. Recent renovations include a new central heating, air conditioning, and ventilation system; new plumbing and electrical throughout; a beautifully updated kitchen with new cabinetry, quartz countertops, and brand-new appliances (dishwasher is original); new engineered hardwood flooring, ceramic tile, and carpet throughout; fully renovated bathrooms featuring new vanities, toilets, tubs/showers, and fixtures; a new water heater; repaired and reinforced floor joists, roof joists, and subflooring where needed; repaired foundation; new attic insulation; brand-new siding; a new roof with 50-year architectural shingles; termite treatment; and a crawl space enhanced with a dehumidifier, insulation, and vapor barrier. Outdoor improvements include a new low-maintenance artificial lumber deck with steps leading to the pier, as well as reset pavers with a new setting bed for the expansive waterfront patio and front sidewalk. Ideally located just minutes from Leonardtown Square, this exceptional waterfront property offers the perfect combination of stunning views, extensive renovations, modern amenities, and convenient access to shopping, dining, and local attractions. Enjoy the best of coastal living in a home where every day feels like a getaway.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,554
Status:
Active
MLS#:
MDSM2031220
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

****December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! ***** Homesite #156 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. Visit the Meadows at Town Run II model home to explore available floor plans and new construction opportunities. Model home hours are Thursday–Sunday, 11 AM–4 PM. Photos shown are representative and intended to illustrate a similar finished townhouse. Please note that buyer's agents must accompany their clients on their first visit. Schedule your tour today!

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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

    $482,450
    12.7%
    change since last quarter
  • # Active listings

    72
    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