Leonardtown MD Real Estate & Homes for Sale

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

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
3.00
Sq.Ft.:
3,372
Status:
NEW LISTING
MLS#:
MDSM2028350
Type:
Single Family-Detached
Subdivision:
Leonardtown Farms
Lot size:
1.08 Acres
Year built:
2010
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

Stunning Dunleigh model by Marrick Homes on over 1 full acre in desirable Leonardtown Farms! 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 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:
NEW LISTING
MLS#:
MDSM2028512
Type:
Townhouse
Subdivision:
Leonardtown Landing
Lot size:
0.05 Acres
Year built:
2005
Courtesy: EXP Realty, LLC 888-860-7369
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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:
NEW LISTING
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
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ADDITIONAL INFORMATION

Contemporary-style home offering exceptional flexibility as a single-family residence or an income-producing property with a private apartment. The freshly painted interior features 5 bedrooms and 3 full baths, including a 2BR/1BA apartment with its own entrance—ideal for multigenerational living, guests, or rental income. The main living level showcases hardwood floors, an open living/dining layout with a fireplace and eat-in kitchen. Multiple sliding doors flood the home with natural light and open to a front deck—perfect for enjoying morning sun and neighborhood views. The kitchen offers charming cottage-style cabinetry, vintage appliances, a wine storage closet, and built-in features. In the main home, two bedrooms and a full bath are located on upper level 1, while upper level 2 is dedicated to a private owner’s suite with an ensuite bath, deep walk-in closet, architectural openings overlooking the main living area, and walk-up access to attic (upper level 3) and its ample storage. The lower level 1 provides access to the laundry closet and storage room of the main home as well as an interior door to access the apartment. The apartment’s exterior entrance is to the right of the two-car garage and hosts a foyer, storage closet, and kitchen on this level. Up the newly carpeted stairs is living space with a private deck, two bedrooms, a full bathroom, and its own laundry in a closet. Additional highlights include a newly installed septic system, a paved driveway with ample parking, high-speed broadband availability, a storage shed with garage door, and new carpet throughout both the home and apartment. A unique opportunity offering space, versatility, and income potential.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,075
Status:
NEW LISTING
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
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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:
3
Baths:
2.00
Sq.Ft.:
1,557
Status:
NEW LISTING
MLS#:
MDSM2028410
Type:
Single Family-Detached
Subdivision:
Hawks Nest
Lot size:
1.37 Acres
Year built:
2025
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

IMMEDIATE DELIVERY! Brand-New Leonardtown Rambler on 1.37 Acres Welcome to a beautifully crafted 1,557 sq. ft. new-build rambler set on 1.37 peaceful acres in one of Leonardtown’s most desirable locations. This home blends modern style with relaxed countryside living, offering a layout designed for comfort, connection, and effortless everyday life. A welcoming front porch and striking red door set the tone as you step inside to an expansive open floor plan. Wide plank flooring, soft natural light, and clean design lines create a warm, inviting atmosphere that flows seamlessly from the living area into the dining space and kitchen. The open layout provides exceptional flexibility, accommodating large sofas, oversized entertainment setups, family gatherings, and quiet evenings alike. The kitchen is the true centerpiece of the home, featuring shaker-style cabinetry in a sophisticated two-tone palette, sleek quartz countertops, stainless steel appliances, and a large island with seating. Pantry cabinetry provides excellent storage and functionality, making this kitchen ideal for both cooking and entertaining. The private primary suite is a peaceful retreat with plush carpet, a walk-in closet, and a dual-vanity ensuite designed for comfort and convenience. Two additional bedrooms are generously sized with ample closet space, perfect for family, guests, or a home office. A nicely sized full bathroom serves the rest of the main floor. Step outside to a wide-open backyard that offers a blank canvas for all your outdoor visions. Whether you dream of a garden, patio, firepit, play area, or outdoor living oasis, the space is here to bring it to life. The setting is quiet and serene, yet only minutes from Leonardtown’s restaurants, shops, waterfront attractions, schools, and everything this historic town has to offer. This brand-new home delivers modern design, practical comfort, and room to grow in a location that balances privacy with convenience. It is the ideal place to begin your next chapter in Southern Maryland.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,500
Status:
NEW LISTING
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
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ADDITIONAL INFORMATION

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,732
Status:
NEW LISTING
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
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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
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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
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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 Step inside and 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
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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
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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
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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!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,920
Status:
Active
MLS#:
MDSM2027998
Type:
Single Family-Detached
Subdivision:
Redgate
Lot size:
1.25 Acres
Year built:
1997
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Classic Private Colonial offers the perfect blend of tranquility and convenience, nestled on a generous 1.25-acre lot that backs to mature trees for ultimate shade and privacy. Outdoor Living: Enjoy entertaining or quiet mornings on the large vinyl deck, overlooking a great yard. The circular paved driveway provides easy access and added convenience. The Home: Featuring a traditional layout, you can enter through the covered front porch or the attached 2-car garage that features plenty of built-in shelves. The main level is designed for living with a family room, kitchen, a separate dining room, and a cozy living room with a gas fireplace. A half bath on the main level adds convenience. Primary Suite: Retreat to the primary bedroom, boasting a high ceiling, a walk-in closet, and an attached primary bathroom. This spa-like space features double sinks, a separate shower stall, and a soaking tub with a gorgeous picture window offering serene nature views. Worry-Free Ownership: Major components are taken care of with a new Roof installed in 2025, a conditioned crawlspace with a dehumidifier, and some freshly painted walls. The property also includes a shed for extra storage and, best of all, NO HOA, NO front-foot fee, and NO deferred water/sewer bill! Prime Location: Located in the desirable Wilderness Woods Neighborhood (Redgate), you are in the most popular and sought-after city of Historic Leonardtown. Enjoy close proximity to NAVAIR Pax River Base, shopping, museums, restaurants, hospital, music venues, historic places, boat ramps, marinas, fishing piers, a winery, watersport rentals, and SO MUCH more! Don't delay, schedule a tour today!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,653
Status:
Active
MLS#:
MDSM2027526
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.5 Acres
Year built:
1981
Courtesy: CENTURY 21 New Millennium 301-609-9000
View additional info

ADDITIONAL INFORMATION

$20,000 PRICE ENHANCEMENT!! Plus CLOSING HELP considered with acceptable offer! Welcome to your retreat in The Valley, where every day feels like vacation! This gorgeous resort style property sits on 1.5 acres in a peaceful, waterfront rich area. Boating, exceptional dining, and scenic sunsets all at your fingertips! This 3 bedroom, 3 full bath home has been impeccably maintained and beautifully updated inside and out including professionally landscaped grounds and extensive hardscaping. The backyard oasis is the ideal space for entertaining or relaxing in style with the wrap-around deck, heated in-ground pool, hot tub, fire pit, pergola, pool house, and a covered stone bar & grill. The main level boasts a spacious and inviting layout. The living room’s tasteful updates include beautiful LVP floors, stone-accent walls, and a pellet stove. Two large bedrooms including an ensuite primary, two full baths, a flexible bonus room, laundry, and two storage closets offer ample space and convenience all on one level. The upper level is equally stunning with vaulted ceilings, exposed wood beams, a sun filled family room, large kitchen with island, granite counters, new stainless-steel smart appliances, and a walk-in pantry. The second primary bedroom features an abundance of sprawling windows, walk-in closet, and entry to a beautifully updated full bath with super shower. Additional highlights include a screened porch, oversized detached garage with HVAC and attic storage, and a large separate workshop with built-ins. Bring all your toys and tools! Major updates/upgrades including roof with architectural shingles, windows, and generator, offer peace of mind. Make sure to check out the “Documents” section for a more detailed list. Located near the Potomac River, Tall Timbers, Piney Point, and St. George’s Island—this home is a dream for outdoor enthusiasts! Easy access to NAS Patuxent River, Route 5, and Route 4. Don’t miss your chance to be the proud new resident of this community and owner of this rare gem!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,888
Status:
Active
MLS#:
MDSM2027792
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.25 Acres
Year built:
2019
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite features a large walk-in closet and a luxury bathroom featuring a soaking tub, huge shower, and two vanities featuring gorgeous decorative tile. The kitchen and family room on the main floor offer a large welcoming space for family and friends with a sliding glass door that goes out to the patio to enjoy the firepit and fenced in back yard. The additional dining room and living room spaces allow you to spread out for large family gatherings. The mudroom joins the garage and is a great space to welcome you home. The basement has a finished studio room for your crafts or hobbies and a large unfinished area for you finish and make it your own.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,527
Status:
Active
MLS#:
MDSM2027122
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.28 Acres
Year built:
1970
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family room with wood stove insert, large laundry room, and accessory area on the lower level. Also has a 2 Car Detached garage built in 2008. Roof of garage and house was re-shingled in 2020 with 50 year shingles. The HVAC was regularly serviced.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,291
Status:
Active
MLS#:
MDSM2027316
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.55 Acres
Year built:
2018
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Welcome to 21920 Newtowne Neck Road! Step inside this inviting Colonial home offering 2,291 sq. ft. of comfortable living space, 4 bedrooms, and 2.5 bathrooms, perfectly situated on a .55-acre lot in Leonardtown. Inside, you’ll find a bright and spacious layout designed for both everyday living and entertaining. The heart of the home features an eat-in kitchen with stainless steel appliances, a center island, and plenty of natural light, opening to a warm and welcoming family room. Step right out onto the deck off the kitchen, ideal for morning coffee, grilling, or hosting gatherings that flow easily into the fenced backyard. Upstairs, the generously sized bedrooms include a relaxing primary suite, while the additional bedrooms offer flexibility for family, guests, or a home office. With its combination of classic Colonial style, modern updates, and an outdoor space ready for fun and relaxation, this home provides the perfect setting to make lasting memories. Located close to schools, shopping, dining, and all the charm of Leonardtown, it’s ready to welcome its next owner.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,018
Status:
Active
MLS#:
MDSM2027780
Type:
Single Family-Detached
Subdivision:
Brubachers
Lot size:
0.18 Acres
Year built:
1950
Courtesy: RE/MAX One 410-535-6291
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ADDITIONAL INFORMATION

Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiast’s paradise. Enjoy the sights and sounds of ospreys, fish, and abundant wildlife right from your doorstep. Key features include: ? Approximate water depth: 2.5 ft at low tide, 4.5 ft at high tide ? Seawall refurbished in 2020 for added shoreline protection ? Private pier with an electric boat lift—perfect for boating adventures Don’t miss this rare chance to own a piece of paradise with endless potential. Whether you’re looking for an investment, vacation retreat, or future dream home, this waterfront gem is a must-see!

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

ADDITIONAL INFORMATION

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

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

ADDITIONAL INFORMATION

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

Beds:
4
Baths:
4.00
Sq.Ft.:
2,472
Status:
Active
MLS#:
MDSM2027150
Type:
Single Family-Detached
Subdivision:
Kingston
Lot size:
1.02 Acres
Year built:
2004
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has all-new flooring and a freshly painted interior. A bright and cheery home with four spacious bedrooms on the upper level, with generous closets. Convenient laundry on this upper level. The main floor features an oversized great room, a kitchen with solid surface counters, and a garden window over the kitchen sink to grow fresh herbs! A front sitting room makes for a sizable home office, opposite a formal DR. The unfinished basement has a full walkout and a finished 3-piece full bath. Enjoy the outdoors, whether on the back deck and patio, the traditional front porch, or garden and play on the 1+ acre lawn. No rear neighbors, this property backs to a conservation area. The original owners have cultivated plantings to attract butterflies and hummingbirds. Kingston is situated off beautiful Medley's Neck Rd., flanked by vast farms. It is a community in which everyone enjoys decorating for the seasons! Kids have plenty of room to play at the neighborhood soccer field and baseball diamond, complete with a great picnic pavilion, tables and grill for group gatherings. Located just minutes from thriving Leonardtown, an easy commute to NAS Pax River.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,526
Status:
Active
MLS#:
MDSM2027750
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.38 Acres
Year built:
2003
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

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

Beds:
2
Baths:
3.00
Sq.Ft.:
2,040
Status:
Active
MLS#:
MDSM2027068
Type:
Single Family-Detached
Subdivision:
Chappelears
Lot size:
0.34 Acres
Year built:
2005
Courtesy: Real Broker, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with a loft on the Potomac River just minutes from historic Leonardtown. Perfectly designed for those who love life on the water, this property features its own private dock complete with a boat lift and fish cleaning station, making it a dream come true for boaters and anglers alike. Inside, you’ll find a spacious and inviting layout filled with natural light throughout. The highlight of the home is the Florida room with panoramic river views, offering the perfect spot to relax, entertain, or simply take in stunning sunsets over the water. The open loft adds flexible living space—ideal for a guest area, office, or hobby room. The kitchen and dining areas flow seamlessly for easy living, while two comfortable bedrooms provide restful retreats. With 2.5 baths, convenience is never in short supply. An oversized 3-car garage provides ample storage for your vehicles, water toys, tools, and more—making it easy to enjoy every aspect of the riverfront lifestyle. Whether you’re searching for a weekend getaway or a year-round residence, this home blends comfort, charm, and direct river access. Enjoy peaceful mornings, afternoons on the water, and evenings watching the river roll by—all from the comfort of your own home. Don’t miss this rare opportunity to own a piece of Potomac River paradise!

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2028148
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Year built:
2025
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

***Immediate Delivery***Builder Incentive, Settle in 2025, Receive $10,000 in Builder Credit plus $12,500 in Closing Help OR $10,000 Builder Credit plus a 2/1 Rate Buydown AND $5,000 Closing Help with Preferred Lender & Title company. Builder to honor promotional pricing for contracts that close by 12/31/25. Unit 106 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 2,604 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, brushed nickel fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard, perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds, all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today!

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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 20650 Real Estate

Leonardtown is located in Maryland. Leonardtown, Maryland 20650has a population of 4,445. Leonardtown 20650 is more family-centric than the surrounding county with 40.08% 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 20650 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 20650 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

    $554,500
    12.7%
    change since last quarter
  • # Active listings

    89
    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
Chesapeake Charter School KG - 08 360 14.1 20653
Dynard Elementary School PK - 05 478 19.2 20621
Evergreen Elementary School PK - 05 795 19.3 20619
George Washington Carver Elementary School PK - 05 644 17 20634
Green Holly Elementary School PK - 05 602 14.6 20653
Greenview Knolls Elementary School PK - 05 408 17.9 20634
Hollywood Elementary School PK - 05 550 18.2 20636
Leonardtown Elementary School PK - 05 789 18.6 20650
Lettie Marshall Dent Elementary School PK - 05 648 19.9 20659
Lexington Park Elementary School PK - 05 540 17.6 20653
Mechanicsville Elementary School PK - 05 384 21.4 20659
Oakville Elementary School PK - 05 304 17.9 20659
Park Hall Elementary School PK - 05 670 17.7 20667
Piney Point Elementary School PK - 05 529 18.7 20690
Ridge Elementary School PK - 05 285 16.5 20680
Town Creek Elementary School KG - 05 234 14.2 20653
White Marsh Elementary School KG - 05 244 16.9 20659

Middle Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Esperanza Middle School 06 - 08 818 16 20653
Leonardtown Middle School 06 - 08 933 15.9 20650
Margaret Brent Middle School 06 - 08 992 17.4 20659
Spring Ridge Middle School 06 - 08 989 16.6 20653

High Schools near Leonardtown, MD

Grades Students P/T Ratio ZIP
Chopticon High School 09 - 12 1,628 21.6 20660
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 20650

Zip Code City
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