Leonardtown MD Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,710
Status:
NEW LISTING
MLS#:
MDSM2033936
Type:
Single Family-Detached
Subdivision:
SINGLETREE
Lot size:
0.24 Acres
Year built:
2001
Courtesy: RE/MAX Realty Group 301-884-9493
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ADDITIONAL INFORMATION

Welcome to this well cared for home! This cape cod features an unfinished walk-in attic for future expansion. Finish it yourself for instant equity or keep it for storage. This home features a first-floor bedroom with walk in closet, linen closet and bath for those of you who do not like stairs. Large kitchen with 3 pantries and peninsula with tons of storage. Breakfast area as well as separate dining area or another family room. Large living room with electric fireplace. Humongous garage with opener and storage. Private vinyl fenced yard features a brick patio. Lovely landscaping with underground sprinkler system. Close to Hospital, Board of education, medical facilities, shopping, restaurants and more.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,344
Status:
NEW LISTING
MLS#:
MDSM2033928
Type:
Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.16 Acres
Year built:
2014
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to this gorgeous home that has been immaculately maintained and thoughtfully upgraded from top to bottom. From the moment you step inside, it feels as though it came straight out of a Pottery Barn magazine, with beautiful finishes, custom craftsmanship, and attention to detail throughout. Gorgeous full-thickness walnut flooring flows throughout the home and is complemented by extensive custom woodworking, including crown molding, shiplap, shadow-box molding, and beautifully built-out fireplace details. Custom millwork can be found throughout the kitchen, family room, living room, office, and bathrooms, while real wood plantation blinds and upgraded lighting add another layer of warmth and sophistication. At the heart of the home is the gourmet kitchen, featuring upgraded cabinetry and appliances, double wall ovens, and an oversized island with a prep sink - perfect for everyday living and entertaining. The eat-in kitchen is positioned perfectly off of the deck. You will also love the dedicated mudroom as you enter in the house from the garage! Upstairs you will find a generously sized primary suite with the serene upgraded bathroom equipped with a garden tub and a huge shower. Two other bedrooms are upstairs with a nice bathroom with double sinks. The upgrades continue into the laundry room, which features wood cabinetry, a utility sink, and oversized washer and dryer. The beautifully finished lower level provides even more living space with a fourth bedroom, dedicated exercise room, and surround-sound wiring. Outside, the setting is just as impressive. The fully landscaped front and backyard have been meticulously maintained, while the premium lot faces the sunset and overlooks an open field, offering a wonderful sense of openness with no front or backyard traffic. The fenced backyard features a large composite deck designed for entertaining, along with a full lawn irrigation system. Even the garage has been upgraded with a durable epoxy-coated floor. Beautifully designed, exceptionally maintained, and filled with high-end details, this home is truly move-in ready and one you won't want to miss.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,306
Status:
Active
MLS#:
MDSM2033744
Type:
Townhouse
Subdivision:
CLARK'S REST PHASE 1
Lot size:
0.06 Acres
Year built:
2018
Courtesy: Infinitas Realty Group 240-925-2224
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ADDITIONAL INFORMATION

Welcome to 41517 Margrove Cir, a beautifully maintained 3-bedroom, 3.5-bath townhome nestled in the highly desirable Clark's Rest community. This spacious and stylish home offers a perfect blend of comfort, convenience, and community living. Inside, you’ll find a bright and open floor plan with generous living spaces, modern finishes, and meticulous upkeep throughout. Each bedroom provides ample space and privacy, including a well-appointed primary suite and a fully finished lower level with a full bath—ideal for guests, a home office, or a recreation room. Enjoy all the community has to offer with access to top-notch amenities including a swimming pool, playground, tennis courts, and a community center—perfect for both relaxation and social gatherings. Outside the neighborhood, you're just minutes away from local favorites such as restaurants, shopping, parks, a movie theater, and more. Conveniently located just a short drive from Naval Air Station Patuxent River, this home is ideal for those seeking both lifestyle and location. Don’t miss your opportunity to live in one of the most sought-after communities in the area—schedule your showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,604
Status:
Active
MLS#:
MDSM2033190
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
2 Acres
Year built:
2004
Courtesy: The Southside Group Real Estate 301-298-2892
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ADDITIONAL INFORMATION

This well-maintained 2004 ranch-style home offers 2,604 square feet of functional living space on a private, non-HOA 2-acre lot. The interior features four spacious bedrooms, three full bathrooms, and an open-concept layout that seamlessly connects the main living and dining areas. A fully finished basement provides flexible additional square footage ideal for a home office, media room, or gym. Outside, the detached two-car garage offers extra parking and storage, while the expansive, unrestricted lot gives homeowners complete freedom for gardening, outdoor recreation, or adding custom structures—combining peaceful country living with convenient access to nearby local amenities.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,314
Status:
Active
MLS#:
MDSM2033568
Type:
Single Family-Detached
Subdivision:
BRETON BAY
Lot size:
1.22 Acres
Year built:
2003
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Nestled in the charming sought after Clearfields community, this stunning Colonial blends modern luxury with everyday comfort. Set on a beautifully landscaped 1.22-acre lot, this 4-bedroom, 2.5-bathroom home provides ample space for both relaxation and entertaining. At the heart of the home is a chef's dream kitchen, featuring custom cabinetry, gorgeous quartz countertops, a designer backsplash, stunning lighting, and stainless steel appliances. Loads of natural light flood the cozy two story family room with a floor to ceiling stone gas fireplace, a flex room, formal dining room, powder room, and mudroom complete the main level. Upper level fresh new carpet, primary suite w/ gas fp , large walk in closet, deluxe bath with dual vanities, soaking tub, and ceramic tiled shower. Additional 3 bedrooms and shared full bath Full unfinished basement with rough in for future bath Step outside to your private outdoor oasis—complete with a refreshing inground pool surrounded by lush greenery, a back porch outfitted for outdoor cooking, and plenty of room for recreation. Beyond the property, enjoy nearby bay access, local parks, walking trails, top-rated schools, and vibrant community events. This property offers more than just a home—it delivers an exceptional lifestyle and a peaceful retreat to create lasting memories

Beds:
3
Baths:
1.00
Sq.Ft.:
2,068
Status:
Active
MLS#:
MDSM2033774
Type:
Other
Subdivision:
X
Lot size:
13.75 Acres
Year built:
1953
Courtesy: Berkshire Hathaway HomeServices PenFed Realty 410-394-0990
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ADDITIONAL INFORMATION

Looking for acreage, privacy, and freedom? Discover this 12.73 acre homestead. This mostly wooded property that offers mature trees, privacy, and zero HOA restrictions located just minutes from Leonardtown, California, Solomons Island, and Naval Air Station Patuxent River. Featuring a vintage 1953 3-bed/1-bath home which is being sold "AS IS", detached garage, and multiple outbuildings, the primary value rests in the vast land and existing infrastructure (well, septic, and electric hookups). The mature trees and the generous acreage provides ample space for a new custom home, a small farm, multi-generational family compound, and potentially ability to subdivide. There were 3 successful perc tests in 2021, according to St. Mary’s County Health Department. The property is Zoned RPD (Rural Preservation District) with agricultural use, so the annual taxes are low. This expansive property offers room to grow, for outdoor living areas, hobbies, hunting, livestock (horses, chickens, or whatever), pets, recreational trails, and more. Affordable acreage with this much potential and accessibility is incredibly rare. Schedule your tour today! **BUYER NOTICE: DO NOT ENTER OUTBUIDINGS! Agents and their clients enter the property entirely at their own risk, releasing the seller from any and all liability or claims arising from such entry. All buyers must perform their own independent due diligence and contact all relevant agencies to verify any and all information regarding development capabilities, zoning restrictions, perc testing, well, septic, and subdivision potential. **

Beds:
4
Baths:
4.00
Sq.Ft.:
3,340
Status:
Active
MLS#:
MDSM2033554
Type:
Single Family-Detached
Subdivision:
CLARK'S REST
Lot size:
0.17 Acres
Year built:
2023
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Discover a luxurious lifestyle in this stunning 2023 Colonial home nestled in the desirable Clark's Rest community. This exquisite residence boasts four spacious bedrooms and three and a half elegantly appointed bathrooms, perfect for both relaxation and entertaining. There are two unfinished bedrooms in the basement, so potentially it can be 6 bedrooms house. The heart of the home features high-end appliances, including an ENERGY STAR refrigerator and built-in microwave, ensuring both style and efficiency in your culinary adventures. Experience the warmth of the cozy fireplace in the inviting living area, while the partially finished basement offers endless possibilities for customization. Step outside to enjoy the community amenities, including a sparkling outdoor pool and tennis courts, all maintained for your convenience. With a two-car attached garage and a beautifully landscaped lot, this home combines comfort and sophistication. Embrace the exclusive lifestyle that awaits you in this exceptional property, where every detail has been thoughtfully designed for modern living.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,736
Status:
Active
MLS#:
MDSM2033334
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.18 Acres
Year built:
2021
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

Welcome to this stunning rambler in the highly sought-after community of Clark's Rest! Thoughtfully designed with 9' ceilings, quartz countertops, designer finishes, and upgrades throughout, this home offers the perfect blend of style, comfort, and functionality.The main level features three spacious bedrooms and two full bathrooms, including a beautiful owner's suite with dual vanities. The open, inviting layout makes everyday living easy while providing plenty of space to entertain.Downstairs, the finished basement adds a fourth bedroom, full bathroom, and generous recreation area—plus over 1,000 square feet of unfinished space ready for your vision. Create a fifth bedroom, home gym or athletic studio, game room, movie theater, workshop, or whatever suits your lifestyle. The possibilities are truly endless!Step outside and enjoy the welcoming front and back porches, perfect for morning coffee, relaxing evenings, or gathering with friends and neighbors. Clark's Rest offers a wonderful small-town feel with an impressive array of amenities, including walking paths, a community pool, clubhouse, and tennis courts.Conveniently located in Leonardtown with easy access to PAX River, local dining, shopping, and everything this charming community has to offer. Beautiful, spacious, upgraded, and loaded with potential—make sure this one is on your must-see list and come see it today!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,731
Status:
Active
MLS#:
MDSM2033518
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
26.62 Acres
Year built:
1956
Courtesy: O'Brien Realty ERA Powered 301-863-2400
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ADDITIONAL INFORMATION

Rare Waterfront Estate in Leonardtown! Nestled on 26.62 scenic acres, this charming Cape Cod farmhouse offers an unbeatable blend of pastoral beauty and waterfront living. Enjoy sweeping views of Blake Creek, extensive water frontage, and a private pier—perfect for kayaking, paddle boarding, crabbing, fishing, and peaceful small motor boating on this quiet tidal inlet. Inside, thoughtful additions provide multiple living spaces for relaxing and entertaining. The main level features a welcoming entry sitting room with a brick-surrounded electric fireplace, a spacious family room with a wood stove, and a dramatic sunroom with vaulted beam ceilings and a wall of sliding glass doors showcasing expansive views of the water. Upstairs from the family room sits a versatile bonus room accented with rustic wood detailing. The main floor primary suite includes a spacious walk-in closet and an updated bath. The additional 2 bedrooms on the upper level are very spacious. The very large detached garage is perfect for parking and projects, or you decide. Surrounded by active farm fields, the setting provides an idyllic, tranquil backdrop—with incredible potential for a custom horse property or private equestrian estate (pending county approval/permits). A truly special opportunity offering land, water, and timeless farmhouse character!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,066
Status:
Active
MLS#:
MDSM2033536
Type:
Single Family-Detached
Subdivision:
LEONARDTOWN FARMS
Lot size:
0.85 Acres
Year built:
2011
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

Exciting New Offer! Sellers are offering $10,000 in buyer assistance to help make this home your own! Put it toward eligible closing costs or an interest rate buydown, and keep more of your own money available for any updates you want. Ask your lender how the credit could work for you. Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of Leonardtown’s most desirable neighborhoods. Tucked near the end of a quiet street by the cul-de-sac, this 4-bedroom, 3.5-bath home offers more than 3,500 square feet of finished living space, a finished basement, and a large, level backyard with room to truly enjoy. Inside, a bright and welcoming floor plan provides plenty of space for everyday living and entertaining. At the heart of the home is the updated kitchen, featuring a large center island with built-in beverage refrigerator, granite countertops, and durable tile flooring that continues into the bumped-out breakfast area overlooking the backyard. Multiple living spaces on the main level make it easy to host a crowd while still feeling comfortable and connected. Outside, the property really shines. The fully-fenced, level backyard offers an incredible amount of usable space for pets, play, gardening, and gatherings. Enjoy summer dinners on the expansive deck, relax beneath the pergola-covered patio, or simply enjoy the privacy of your nearly one-acre lot. A large storage shed provides additional space for lawn equipment and outdoor gear. Upstairs, the oversized primary suite offers a spacious walk-in closet and the added convenience of laundry hookups. Three additional generously sized bedrooms with ample closet space complete the upper level. The finished basement adds even more flexibility with a large recreation area, full bathroom, bonus room, and unfinished storage space. Whether you need a home office, gym, playroom, hobby space, or guest area, there is room to make it your own. A side-load two-car garage rounds out a home designed for buyers who want room to spread out without giving up the neighborhood feel. Fairwood Ct. offers the kind of community atmosphere so many buyers are looking for—a place for evening walks, bike rides, backyard gatherings, and putting down roots—all while enjoying the space and privacy of a larger lot. Over 3,500 finished square feet, 4 bedrooms, 3.5 bathrooms, a finished basement, nearly an acre, a fenced backyard, and an updated kitchen—all in Leonardtown. Come see just how much 21395 Fairwood Ct. has to offer.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,953
Status:
Active
MLS#:
MDSM2033456
Type:
Single Family-Detached
Subdivision:
WHISPERING PINES
Lot size:
4.24 Acres
Year built:
2015
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Welcome to this beautiful custom-built home situated on over 4 acres, offering an incredible combination of space, privacy, and versatility. A welcoming covered front porch and mature landscaping create beautiful curb appeal and the perfect place to sit back and enjoy the peaceful surroundings. Inside, you’ll find a thoughtfully designed floor plan featuring a main-level primary suite, spacious formal dining room, and a kitchen with a cozy breakfast nook. The impressive living room features a two-story ceiling, creating a bright, open feel and a beautiful centerpiece for the home. Upstairs, you’ll find additional bedrooms, including an oversized bedroom that offers plenty of flexibility and could easily serve as a second living room, hangout space, game room, or media room. With 5 bedrooms in total, there is room for everyone to spread out. Outside, the property continues to impress with a large, attached garage plus a detached garage with workshop—perfect for hobbies, projects, vehicles, or additional storage. The more than 4-acre property offers a wonderful mix of clear and wooded space, including a large open area ideal for gardening, recreation, entertaining, or simply enjoying your own backyard. ATV and outdoor enthusiasts will love the trails winding throughout the property. From the inviting front porch to the flexible interior spaces, multiple garages, workshop, and acreage to explore, this one-of-a-kind property offers room to live, play, work, and make it your own.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,562
Status:
Active
MLS#:
MDSM2033062
Type:
Single Family-Detached
Subdivision:
ACADEMY HILLS
Lot size:
0.2 Acres
Year built:
2005
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

Interior Photos Coming Soon! Expected on market date is Sept 1, 2026 Welcome to 41888 Jenkins Court in the highly desirable Academy Hills community of Leonardtown! Perfectly situated within walking distance of the Leonardtown Wharf and historic Leonardtown Square, this exceptional home places you just moments from charming shops, local dining, breweries, community events, and all that downtown Leonardtown has to offer. Built by P.F. Summers, this beautifully maintained residence offers an inviting blend of elegance, comfort, and functionality. From the moment you arrive, the professionally designed landscaping and welcoming wraparound front porch create an impressive first impression, while the peaceful cul-de-sac setting adds to the home's appeal. Inside, the main level features a traditional yet comfortable floor plan with a formal living room and dining room, perfect for entertaining or more intimate gatherings. The spacious kitchen offers upgraded cabinetry, a center island, upgraded countertops and lighting, a new refrigerator, and a new built-in microwave. Just off the kitchen, the family room provides the ideal gathering space, complete with a gas fireplace and mantel. Upstairs, the spacious primary suite is sure to impress, featuring soaring cathedral ceilings, a generous walk-in closet, and a luxurious private bath. An additional bedroom suite offers its own full bath, providing an ideal space for guests or extended family. Two additional bedrooms share a conveniently located hall bath, offering plenty of room for family and guests. The lower level presents an exciting opportunity to create a space tailored to your lifestyle. Partially started, it is ready for the new owners to finish and customize as desired. A rough-in for a future full bath is already in place, and the walk-out design provides direct access to the fenced rear yard. Step outside and enjoy the beautifully landscaped surroundings, private fenced yard, and the charm of relaxing on the wraparound front porch overlooking the quiet cul-de-sac. Located just a short drive from Patuxent Naval Air Station, this home offers an ideal combination of convenience and lifestyle, with easy access to local beaches, parks, museums, restaurants, theaters, marinas, and more. Come experience the charm, convenience, and character of 41888 Jenkins Court — and discover why there is no better time to call Leonardtown home!

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
View additional info

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
View additional info

ADDITIONAL INFORMATION

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:
4.00
Sq.Ft.:
4,744
Status:
Active
MLS#:
MDSM2033138
Type:
Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.32 Acres
Year built:
2015
Courtesy: CENTURY 21 New Millennium 301-862-2169
View additional info

ADDITIONAL INFORMATION

Welcome home to the Hampton model, featuring fresh paint, newer flooring, and updated carpet throughout! The main level showcases a welcoming two-story foyer and a soaring two-story family room flooded with natural light, along with dedicated formal living and dining room, a private study, and a chef-inspired grand kitchen with an expansive center island. Main level bedroom with a full bath for those not wanting steps. Upstairs, you’ll find four spacious bedrooms, two full baths, and a convenient upper-level laundry room. The fully finished lower level offers a fifth bedroom and additional full bath—providing plenty of flexible space for recreation, a home gym, or guests, plus abundant extra storage. All of this sits on a premium lot backing to open green space, offering a wonderful sense of privacy and serene views. Experience everything Leonard’s Grant community has to offer! Take advantage of neighborhood amenities like the community pool, basketball and tennis courts, rec center, and neighborhood parks. You're just a short walk from the nearby elementary school, updated Leonardtown Library and minutes from the heart of Leonardtown Square, where you can enjoy local dining, shopping, and beautiful views along the water.

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
View additional info

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
View additional info

ADDITIONAL INFORMATION

*** November Delivery ***ALMOST READY**** ***Builder Incentive $12,500 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. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
5
Baths:
3.00
Sq.Ft.:
1,080
Status:
Active
MLS#:
MDSM2033116
Type:
Other
Subdivision:
NONE AVAILABLE
Lot size:
0.3 Acres
Year built:
2005
Courtesy: Century 21 Redwood Realty 301-208-2288
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ADDITIONAL INFORMATION

Located on a private lot in Leonardtown, this 5 bedroom 3 full bathroom house has been updated and is ready for a new owner! Move right in and make it your own home. The upper level features an open kitchen with breakfast bar, formal dining & living rooms. There are 3 bedrooms and a full bathroom in the hallway. The primary bedroom has it's own bathroom. The lower level has 2 additional bedrooms and a full bathroom. Rec room with sliding door access to the level back yard. The back yard is a perfect space to relax, grill out or entertain. Close to schools, shopping and area amenities. Easy drive to downtown Leonardtown where you will find year round activities including the annual Veterans Day Parade, Christmas on the square and much more. Make your online showing appointment today.

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:
5
Baths:
4.00
Sq.Ft.:
4,084
Status:
Active
MLS#:
MDSM2032818
Type:
Single Family-Detached
Subdivision:
CLARK'S REST
Lot size:
0.21 Acres
Year built:
2019
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Located in the sought-after Clark's Rest community, this home features Marrick’s Kensington floor plan with a covered front entry and separate sitting porch. Inside, the two-story foyer opens to a formal dining room and versatile office, library, or playroom. The kitchen features a large center island, granite countertops, gas cooktop, double wall ovens, abundant cabinetry, butler’s pantry, and walk-in pantry, and opens to the family room with gas fireplace. Upstairs, the owner’s suite offers two walk-in closets with custom closet systems and a private bath with double vanity, soaking tub, and tiled walk-in shower with dual shower heads. Three additional bedrooms, a full bath, and laundry room complete the upper level. The finished walk-out lower level includes a spacious recreation room, fifth bedroom with walk-in closet currently used as a fitness room, and full bath. Outside, enjoy a composite deck, patio, raised garden beds, and fully fenced backyard. Seller is offering a one-year American Home Shield home warranty. *** VA Loan Assumption Opportunity: Seller's existing VA loan carries a 3.5% interest rate and may be assumable by a qualified buyer, subject to lender/servicer approval and applicable VA requirements. *** Clark's Rest offers a variety of community amenities, including a pool, clubhouse, playgrounds, tennis courts, sidewalks, jogging trails, and more. Just minutes from downtown Leonardtown, shopping, dining, and the Leonardtown Wharf, the home is conveniently located near many of the area's destinations. Schedule your private tour today!

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:
2.00
Sq.Ft.:
2,474
Status:
Active
MLS#:
MDSM2032856
Type:
Single Family-Detached
Subdivision:
BRETON BAY
Lot size:
0.66 Acres
Year built:
1975
Courtesy: Real of Pennsylvania 855-450-0442
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ADDITIONAL INFORMATION

Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished lower level expands the living space with an additional family room, two more bedrooms, and a second full bathroom—ideal for guests, a home office, or multi-generational living. With great bones and endless possibilities, this home is ready for your personal touches and updates. Fantastic location just minutes from shops, restaurants, schools, and waterfront amenities on Brenton Bay. Don't miss this rare opportunity to invest in one of Leonardtown's most desirable neighborhoods and create lasting value. Property is being sold strictly as-is. Schedule a showing 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

    N/A
  • # Active listings

    66
    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