Leonardtown MD Real Estate & Homes for Sale

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Beds:
5
Baths:
3.00
Sq.Ft.:
2,601
Status:
NEW LISTING
MLS#:
MDSM2034420
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

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. 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. Offers may be entered ONLINE through Thursday, November 12, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME. AGENT REMARKS: OFFERS: POSTED PRICE IS THE STARTING POINT FOR OFFERS. Submit ONLINE via HomeSale.plus (https://homesale.plus/Listing/Details/11829943). Do not send a full contract; submit a 60-second online offer instead. DEADLINE: Thursday, November 12, 2026 at 5:00 pm. Note: Seller may accept an offer at any time. STEPS: See "3-Step Offer Guide" in MLS Documents. SHOWINGS: Schedule online via Showing Time. REQUIREMENTS: Upload Pre-Approval / POF. Standard contingencies (Inspection/Financing) are allowed. Property being sold AS-IS. QUESTIONS: Property details: contact the Listing Agent / Homesale.plus: 410-441-5443. -- One attachment • Scanned by Gmail Hi Christine, Thanks, I will get this updated in the MLS today. Thanks,

Beds:
5
Baths:
3.00
Sq.Ft.:
2,666
Status:
NEW LISTING
MLS#:
MDSM2034388
Type:
Single Family-Detached
Subdivision:
VILLAGES AT LEONARDTOWN
Lot size:
0.29 Acres
Year built:
2004
Courtesy: Home Towne Real Estate 410-286-9632
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ADDITIONAL INFORMATION

Excellent Leonardtown location, close to Saint Mary’s Hospital, easy commute to NAVAIR. This home features five generously sized bedrooms including bedroom and full bath on main level. Traditional colonial floor plan, entry level two story foyer, office/flex room, formal dining room, spacious family room open to kitchen, full bath and that main level bedroom off kitchen as well. Upper level has four bedrooms including owners suite with walk in closet and private bath, laundry, hall bath and three additional bedrooms. Concrete driveway with room for at least four cars plus attached two car garage, level fenced yard. Full unfinished basement gives plenty of storage space. Excellent schools, close to shopping, restaurants and all that historic Leonardtown has to offer.

Beds:
4
Baths:
3.00
Sq.Ft.:
4,395
Status:
NEW LISTING
MLS#:
MDSM2034286
Type:
Single Family-Detached
Subdivision:
BEECHS ROOST SUBDIVISION
Lot size:
128.07 Acres
Year built:
1971
Courtesy: Samson Properties 443-975-7555
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ADDITIONAL INFORMATION

Rare opportunity to own your own 128.07 acre farm with charming rambler in Leonardtown. Updated professional pics coming soon.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,006
Status:
Active
MLS#:
MDSM2033840
Type:
Single Family-Detached
Subdivision:
CLARK'S REST
Lot size:
0.16 Acres
Year built:
2014
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

This charming home in the desirable Clark's Rest community offers a perfect blend of comfort and modern living. With 4 spacious bedrooms and 3.5 baths, the open floor plan invites you to enjoy gatherings in the family room, seamlessly connected to the kitchen. The kitchen has stainless steel appliances, including a built-in microwave and plenty of counter space, making meal prep a delight. Relax in the primary suite featuring a luxurious soaking tub and walk-in closet. Step outside to enjoy community amenities, including an outdoor pool, tennis courts, and playgrounds, perfect for leisure and recreation. The neighborhood is well-maintained, with snow removal and common area upkeep included in the association fee. Community pool, playground, & clubhouse enhance the community's appeal. With a fully finished basement and a two-car garage, this home is ready for you to create lasting memories. Experience the warmth and charm of Clark's Rest today!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,976
Status:
Active
MLS#:
MDSM2034276
Type:
Other
Subdivision:
BRETON BAY
Lot size:
0.64 Acres
Year built:
1991
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

Updated, upgraded, and NO HOA! This Leonardtown gem has the features buyers are looking for, starting with a stunning custom kitchen featuring 42-inch cabinets, granite countertops, stainless steel appliances, and a farmhouse sink overlooking the backyard. Fresh paint, updated lighting, refreshed flooring, upgraded bath fixtures, and a refaced fireplace give the interior a fresh, modern feel. Outside, enjoy the new stamped concrete patio and walkways, perfect for entertaining or unwinding. Generously sized bedrooms and a desirable corner lot add even more to love. And the bonus? Enjoy access to Breton Bay amenities, including the dock, beach, playgrounds, and picnic areas—all without an HOA! For the pets, there is an invisible dog fence in the front & back yards, as well as a pet door for easy access. Come see everything this home has to offer.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,264
Status:
Active
MLS#:
MDSM2034242
Type:
Single Family-Detached
Subdivision:
CLARK'S REST PHASE 2
Lot size:
0.15 Acres
Year built:
2018
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

**********VA Assumption Available at 3.35%****** Welcome to 41427 Osborne Lane, where a charming covered front porch, striking red front door, and beautiful architectural details create an inviting first impression! Located in Clark’s Rest, this Chaptico model offers 4 bedrooms, 3.5 baths, and 3,379 square feet of living space across three finished levels. With fresh paint, new carpet, and new upgraded stainless steel appliances, this home is ready for its next chapter. Inside, nine-foot ceilings and hardwood flooring in the foyer, kitchen, and formal dining room bring warmth and elegance to the main level. The formal dining room provides a lovely setting for holiday meals, dinner parties, and special occasions, while the kitchen and adjoining breakfast area offer comfortable space for everyday meals and conversation. Rich, dark upgraded cabinetry, a decorative tile backsplash, recessed lighting, and a center island with seating space make the kitchen both attractive and functional. Whether preparing a quiet dinner or hosting a gathering, there is room to cook, serve, and stay connected. The spacious primary suite is a welcoming retreat, highlighted by a dramatic tray ceiling, a ceiling fan, and a trio of windows that fill the room with natural light. Its private bath offers a corner soaking tub beneath a window, a separate enclosed shower, ceramic tile flooring, and upgraded tile at the shower walls and tub surround. A vanity with a seated dressing area adds a thoughtful touch to the space. Three additional bedrooms provide flexibility for guest accommodations, a home office, or hobbies, while upgraded cabinetry throughout the home adds a cohesive finish. The finished walk-out basement extends the living space even further, with a full bath and room to create the spaces that suit your lifestyle. Imagine movie nights, a game room, a workout area, or a comfortable spot to unwind. Direct access to the backyard makes it easy to enjoy both indoor and outdoor living. Outside, the fenced backyard offers space for outdoor gatherings, gardening, or simply enjoying some fresh air, while the newly installed outdoor sprinkler system helps simplify lawn care. Start your morning with a cup of tea on the covered front porch or settle in at the end of the day and enjoy the neighborhood surroundings. A two-car rear-entry garage provides convenient parking while allowing the home’s welcoming front exterior to take center stage. Conveniently located near shopping, dining, and the charm of downtown Leonardtown, with its local boutiques, community events, and waterfront wharf. Enjoy easy access to everyday essentials and area recreation, along with a convenient location for commuting to NAS Patuxent River, MedStar St. Mary’s Hospital, and other Southern Maryland destinations. With its fresh updates, distinctive ceiling details, generous living space, and versatile three-level layout, this Clark’s Rest home offers a beautiful setting for everyday living and entertaining. Come discover all that 41427 Osborne Lane has to offer!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,379
Status:
Active
MLS#:
MDSM2034160
Type:
Townhouse
Subdivision:
CLARK'S REST
Lot size:
0.05 Acres
Year built:
2022
Courtesy: The Southside Group Real Estate 301-298-2892
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ADDITIONAL INFORMATION

Welcome to this like-new townhouse in the sought-after Clark’s Rest community in Leonardtown, Maryland! Built in 2022 and meticulously maintained by its original owners, this beautiful townhouse offers thoughtfully designed living space, featuring 3 spacious bedrooms, 3 full bathrooms, 1 half bathroom, and an attached 2-car garage. Step inside to a bright, inviting open floor plan filled with natural light. The beautifully appointed kitchen features attractive countertops and a spacious island, seamlessly connecting to the family room and dining area, perfect for everyday living and entertaining. The generous primary suite offers a relaxing retreat with a walk-in closet and a private bathroom complete with a soaking tub. Two additional bedrooms provide flexibility for guests, a home office, or whatever suits your lifestyle. Thoughtful upgrades truly set this townhouse apart! Enjoy the convenience of an included washer and dryer, low-maintenance gutter helmets, and an AI-powered watering system. The attached 2-car garage features sleek epoxy flooring and a unique garage screen system, transforming the space into a versatile area where you can relax and enjoy the fresh air. Out back, mature trees create a peaceful, wooded backdrop. Living in Clark’s Rest means enjoying fantastic community amenities, including a swimming pool, tennis courts, and scenic walking paths, all in the charming town of Leonardtown. Move-in ready, beautifully maintained, and packed with upgrades, this Clark’s Rest townhouse offers the perfect combination of comfort, convenience, and modern living. Schedule your private showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,666
Status:
Active
MLS#:
MDSM2034216
Type:
Single Family-Detached
Subdivision:
BEAUVUE EAST
Lot size:
1 Acres
Year built:
1988
Courtesy: Coldwell Banker Premier 301-645-1700
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ADDITIONAL INFORMATION

Room to spread out comes naturally in this spacious split-foyer home, set on a level one-acre lot with no HOA. The generous setting offers flexibility for outdoor entertaining, gardening, play, or simply enjoying a little extra breathing room without a rulebook hovering nearby. Inside, the main floor delivers 4 bedrooms and 3 full bathrooms, a large family room just off the kitchen and a separate living room. With a full bathroom in the basement, the lower level adds valuable versatility for recreation, hobbies, visitors, or a comfortable retreat away from the main living areas. A oversized attached 2-car garage provides sheltered parking and plenty of room for tools, sporting gear, and the household extras that never seem to travel light. The broad, level grounds also make outdoor plans refreshingly simple, whether your vision includes a patio, fire pit, garden beds, or flexible open space. Schedule a private tour and see how well this property fits your next chapter. If property was built prior to 1978, Lead Based Paint Potentially Exists. Seller does not pay customary closing costs, title policy, escrow fees, survey or Transfer/Recordation fee. SOLD AS IS.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,750
Status:
Active
MLS#:
MDSM2034012
Type:
Single Family-Detached
Subdivision:
SOCIETY HILL
Lot size:
0.62 Acres
Year built:
2004
Courtesy: RE/MAX Realty Group 301-855-8600
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ADDITIONAL INFORMATION

Beautiful colonial in Breton Bay with no HOA, over 3,700 finished square feet across three levels, four bedrooms upstairs, and a private, tree-lined backyard on approximately 0.6 acres. A spacious front porch welcomes you inside to hardwood floors, 9-foot ceilings, crown molding, and custom main-level blinds. The kitchen features maple cabinets and a large pantry and opens to the family room with a gas fireplace. Enjoy the covered, screened back porch with a ceiling fan and a separate deck with a hot tub. The front and back porches feature Trex decking and vinyl railings. Upstairs, the primary suite includes crown molding, a spacious walk-in closet, and an updated bathroom with a remodeled walk-in shower, two sinks, and a large closet. Three additional bedrooms and a second full bathroom complete this level, with hardwood flooring and newer carpet. The finished walkout basement includes a game area with some 9-foot ceilings and crown molding, a full bathroom, flexible space for movies, crafts, exercise, or play, and a 210 sqft unfinished storage area with new LVP flooring. Additional features include a two-car garage, tankless water heater, new washer and dryer in 2026, and a shed. For a $75 annual fee, residents can enjoy community beach access on Breton Bay, about 1.4 miles away, with a sandy beach, playground, pavilion, fire pit, and pier. Membership is optional. Nearby, Breton Bay Golf & Country Club also offers golf, swimming pools, and tennis, with separate memberships available.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,306
Status:
Active
MLS#:
MDSM2034018
Type:
Townhouse
Subdivision:
CLARK'S REST PHASE 1
Lot size:
0.06 Acres
Year built:
2017
Courtesy: Berkshire Hathaway HomeServices PenFed Realty 410-394-0990
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ADDITIONAL INFORMATION

Exceptional Upgrades, Thoughtful Design & Outstanding Value in Clark’s Rest Welcome to this beautifully appointed, move-in-ready townhouse in the desirable Clark’s Rest community. Offering extensive upgrades and a finished lower level, this home delivers exceptional value. This home‘s front-foot fee has been PAID IN FULL, saving the next owner more than $15,000 in future assessments. In addition, the roof was replaced in 2024 with GAF shingles, and the lifetime system warranty conveys—providing valuable peace of mind for years to come. The main level of the townhouse features crown molding, custom lighting, and beautiful hardwood flooring throughout. The spacious dining room flows into the well-appointed kitchen, complete with a large center island and peninsula, abundant cabinetry, expansive granite countertops, and gas cooking. The layout is ideal for both everyday living and entertaining. Upstairs, three comfortable bedrooms and two full baths provide plenty of space. Durable COREtec Soft-Step LVP flooring extends through the hallway and two bedrooms for a stylish, easy-care finish. The spacious primary suite includes an elegant tray ceiling and three closets, including an oversized walk-in closet with a functional shelving system. The en-suite bath offers a dual vanity and large soaking tub, while the conveniently located laundry room includes the front-loading washer and dryer. The finished lower level adds valuable living space including another full bathroom, a convenient drop zone, and a large bonus room with COREtec LVP flooring. Use it as a home theater, guest suite, playroom, fitness area, office, or flexible recreation space—the possibilities are yours. Outdoor living is equally appealing. Step from the kitchen onto the expansive maintenance-free deck, perfect for morning coffee, summer gatherings, and entertaining. A large rear-entry two-car garage provides convenient parking and storage, while the tankless water heater adds energy-efficient comfort. Clark’s Rest offers an amenity-rich lifestyle with a clubhouse, swimming pool, playground, sports courts, and walking trails, all conveniently located near the shopping, restaurants, and waterfront attractions of downtown Leonardtown. With its extensive upgrades, flexible finished space, and significant savings on the front-foot fee, this is more than a townhouse—it’s a move-in-ready home with exceptional value in one of Leonardtown’s most desirable communities.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,462
Status:
Active
MLS#:
MDSM2033914
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
5.84 Acres
Year built:
2008
Courtesy: CENTURY 21 New Millennium 301-609-9000
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ADDITIONAL INFORMATION

Discover an exquisite retreat and potential farmette nestled on 5.84 acres of serene rural landscape with no HOA, where luxury meets tranquility. This stunning raised ranch home, built in 2008, boasts an open floor plan that seamlessly blends elegance and comfort. Step inside to find three spacious bedrooms and two beautifully appointed bathrooms, featuring a walk-in shower and stall shower for a spa-like experience. The gourmet country kitchen, equipped with stainless steel appliances, invites culinary creativity, while the adjoining dining area offers future relaxing Sunday dinners. Enjoy evenings on the expansive deck offering picturesque views of the lush lawn and wooded surroundings or cozy up on the charming porch, perfect for savoring a good book and the peaceful ambiance. With smart home features, ample parking and secure storage options, this property is designed for both convenience and style. The unfinished walkout basement presents endless possibilities for customization. Embrace an exclusive lifestyle in this remarkable home, where nature and luxury harmoniously coexist.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,764
Status:
Active
MLS#:
MDSM2034058
Type:
Other
Subdivision:
LEONARDTOWN LANDING
Lot size:
0.05 Acres
Year built:
2005
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Welcome to Leonardtown Wharf, where waterfront views, walkability, and low-maintenance living come together in one of Leonardtown’s most sought-after communities. These townhomes rarely become available, making this a unique opportunity to own a spacious three-level residence in an exceptional location. Offering nearly 2,800 square feet, this four-bedroom, three-and-a-half-bath townhome features hardwood flooring throughout most of the home and an abundance of indoor and outdoor living space. The main level offers an open and comfortable layout with a distinctive kitchen and dining area featuring trendy checkerboard flooring. The living room opens to a large double deck overlooking the front of the property, creating an ideal space for relaxing or entertaining. The outdoor living continues throughout the home, with additional private decks located off each level on the rear of the townhome. Upstairs, two of the bedrooms have direct access to the large front deck, providing even more opportunities to enjoy the surrounding views and outdoor space. The entry-level bedroom offers excellent flexibility and can easily function as a fourth bedroom, recreation room, home office, or additional living space. An elevator provides convenient access between all three levels, making everyday living easier and eliminating the need to carry groceries, luggage, or other items up the stairs. A spacious two-car garage provides plenty of room for parking and additional storage. Beyond the home, Leonardtown Wharf offers beautiful water views, a park at the wharf, and a small pier for enjoying the waterfront. Downtown Leonardtown is just an easy walk away, with local restaurants, shops, entertainment, and other amenities right outside your door. With its generous living space, multiple decks, elevator, two-car garage, and highly desirable waterfront location, this is a rare opportunity to own one of the limited townhomes available at Leonardtown Wharf.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDSM2033908
Type:
Single Family-Detached
Subdivision:
CHESTNUT RIDGE
Lot size:
2.7 Acres
Year built:
1991
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

Welcome to 43261 Cedarwood Ct! Set on a private 2.7-acre lot, this contemporary home offers four bedrooms, 2.5 bathrooms, and space to make your own. The large kitchen and eat-in dining area overlook a spacious deck and fenced backyard. A two-story sunroom brings in natural light, and a wood-burning fireplace in your living room adds warmth. One bedroom is on the main floor and could also serve as a home office. A long paved driveway, completed in 2025, leads to the large attached two-car garage. The roof was replaced in 2019. With room for updates, this home is ready for your vision.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,568
Status:
Active
MLS#:
MDSM2034038
Type:
Single Family-Detached
Subdivision:
LANEDON
Lot size:
0.47 Acres
Year built:
1968
Courtesy: RE/MAX United Real Estate 301-702-4200
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ADDITIONAL INFORMATION

?? INVESTOR ALERT! FIRST-TIME HOME BUYER OPPORTUNITY! Looking for a property where you can build equity and make it your own? This estate sale is a fantastic opportunity for an investor, first-time homebuyer, or anyone looking for some sweat equity in a beautiful waterfront community! Recently occupied and livable as-is, this 3-bedroom, 2-bath home is ready for some updating and personal touches. The home sits on an absolutely gorgeous lot and features a large back deck, perfect for relaxing, entertaining, and enjoying the peaceful surroundings. And it gets even better! The detached 2-car garage offers additional space for a workshop, hobbies, or storage, plus a convenient half bath. With the right vision and some updating, this property has the potential to truly shine. Whether you're looking for your first home, an investment property, or an opportunity to create instant sweat equity, this one is worth taking a look at. Great home, beautiful lot, waterfront community, and tons of potential! ? Bring your vision and make this one your own!

Beds:
5
Baths:
2.00
Sq.Ft.:
2,056
Status:
Active
MLS#:
MDSM2034002
Type:
Single Family-Detached
Subdivision:
LEONARDTOWN
Lot size:
0.94 Acres
Year built:
1965
Courtesy: EXP Realty, LLC 866-825-7169
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ADDITIONAL INFORMATION

New Price and Opportunity! Completely renovated and move-in ready! Welcome to this beautifully updated 5-bedroom, 2-full-bath home set on approximately 1 acre in a convenient Hollywood location. Offering over 2,000 square feet of finished living space, this home combines modern updates with flexible living space and the peace and privacy of a generous lot. Step inside to find brand-new LVP flooring throughout the main living areas, new carpet in the bedrooms, fresh interior paint, and updated lighting and fixtures. The heart of the home is the stunning new kitchen featuring custom cabinetry, quartz countertops, stylish backsplash, stainless steel appliances, a large tile floor, a pantry, and a dedicated breakfast area. The main level offers exceptional flexibility with two separate living areas, two bedrooms, and a brand-new full bathroom, creating the potential for comfortable one-level living. The main living room features a fireplace with a beautiful brick surround and direct access to the deck—perfect for relaxing or entertaining. A separate laundry room is included. Upstairs, you'll find three additional bedrooms and another brand-new full bathroom, providing plenty of space for family, guests, a home office, or hobbies. The extensive improvements continue outside and include a brand-new HVAC system, electrical panel, roof, gutters, and deck, along with some new windows. The exterior has been freshly painted, the landscaping has been refreshed, trees have been professionally trimmed, and the property has been thoughtfully improved to create an inviting outdoor setting. Enjoy the covered front porch, spacious yard, private deck, and approximately 1 acre of property—plenty of room to relax, entertain, garden, or simply enjoy the outdoors. Ideally located in the Hollywood/Leonardtown area with convenient access to shopping, dining, schools, commuter routes, and the Patuxent River area, while still offering the space and tranquility of a larger homesite. Beautifully renovated, exceptionally flexible, and truly move-in ready—come see all that this home has to offer!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,218
Status:
Active
MLS#:
MDSM2034000
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.6 Acres
Year built:
1953
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Over 1/2 Acre No HOA One-Level Living: Set on a level 0.60-acre lot, this home offers approximately 1,200 square feet of living space. New flooring and fresh paint throughout provide a clean, refreshed interior, while the covered front porch adds a welcoming touch. Conveniently located near historic downtown Leonardtown, Leonardtown Wharf, and just a short commute to Naval Air Station Patuxent River.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,460
Status:
Active
MLS#:
MDSM2033960
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
1.87 Acres
Courtesy: RE/MAX One 443-771-8009
View additional info

ADDITIONAL INFORMATION

TO-BE-BUILT opportunity in Breton Knolls! Welcome to Lot 23, a rare opportunity to build a brand-new Quality Built Homes, Inc. home on approximately 1.87 acres in an established Leonardtown community. The builder is currently moving forward with plans and permitting for the Willow floor plan on this homesite. Buyers who act early may have the opportunity to discuss other available Quality Built Homes floor plans that could be considered for the lot (Hampton or Lancaster), subject to builder approval, site feasibility, permitting, and timing. (This lot will NOT accommodate a single-story home - Only a two story). Enjoy the best of both worlds...new construction with room to spread out! Breton Knolls is a small, 24-lot community featuring generously sized homesites, offering a more spacious setting while still keeping you convenient to everything Leonardtown has to offer. Buyers will have the opportunity to meet with the builder’s representative at the Quality Built Homes model home in Leonardtown to review the floor plan, available options and selections, and anticipated construction and delivery timelines. Depending on timing and construction milestones, buyers may also have the opportunity to personalize select finishes and features. The Willow is currently planned for this homesite and offers the thoughtful design, quality construction, and attention to detail Quality Built Homes is known for throughout Southern Maryland. Located just outside the heart of Leonardtown, Breton Knolls offers convenient access to historic Downtown Leonardtown, local shopping and dining, parks, waterfront recreation at Leonardtown Wharf, schools, and commuter routes...all while coming home to nearly two acres of your own space. Get in early and be part of the process from the beginning! Final home design, options, pricing, permitting, and delivery timeline are subject to builder approval and construction schedule. Quality Built Homes, Inc. has a model home nearby at Meadows at Town Run II in Leonardtown. Schedule an appointment to tour the model, explore available floor plans, and learn more about building your new home at Lot 23 in Breton Knolls.

Beds:
5
Baths:
3.00
Sq.Ft.:
4,836
Status:
Active
MLS#:
MDSM2033984
Type:
Single Family-Detached
Subdivision:
LEONARDS GRANT
Lot size:
0.18 Acres
Year built:
2010
Courtesy: Taylor Properties 301-970-2447
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ADDITIONAL INFORMATION

Welcome to 23636 Hansel Court in the desirable Leonards Grant community! This well-appointed home features beautiful hardwood floors, a gourmet kitchen, an attached 2-car garage, and thoughtful upgrades throughout. The mostly finished basement offers excellent flexible space, including a dedicated theater area, office, bonus room, and a unique secret room for extra privacy or storage. Enjoy peace of mind with a brand-new tankless water heater (installed late 2025) and a fully fenced backyard with a 6-ft white vinyl privacy fence - perfect for pets, play, or relaxing. The home was previously approved for daycare use. Community amenities include a pool, tennis court, basketball court, playgrounds, and recreation center. Conveniently located near the elementary school and just a short distance to Leonardtown Square with restaurants, shops, and waterfront views. Don't miss this opportunity!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,248
Status:
Active
MLS#:
MDSM2033970
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
18.03 Acres
Year built:
2008
Courtesy: O'Brien Realty ERA Powered 301-863-2400
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ADDITIONAL INFORMATION

Rare opportunity in Leonardtown! Very private farmstead property with 18.03 acres and a horse barn. The owners have tastefully planted several fruit trees, installed soaker-hose irrigation throughout the orchard, and protected them with fencing so they can mature. The grounds are beautiful and level, with a raised garden with soaker-hose irrigation, also protected by fencing. A composting area is already established on the grounds. The well-built barn has room for 1 horse, a tack room, and 2 storage areas on the main level. The upper level could be used for hay or storage. The property has some fencing, but the new owner would need to complete it if they want to keep a horse. Also included is a storage shed, great for garden tools. This lovely brick-and-vinyl Colonial offers 2,959 sq. ft. of above-grade living space, including 9 ft. ceilings on the main level, 2 story foyer, hardwood on the main level, an upgraded kitchen with a 6-burner propane cooktop, double ovens (one is a convection oven), backsplash, quartz countertops, a center butcher-block island, a breakfast island, and a pantry. Side entry to a mud room in between the oversized 2-car garage. A spacious breakfast area off the kitchen has a French door leading to the massive screened-in porch. The family room is open to the kitchen and has built-in bookcases on each side of the gas fireplace. There's a formal dining room with decorative trim, a tray ceiling, and built-in display corner shelving. Also on the main level is a room that could be used as a library, office, music room, or sitting room. All the rooms have lots of windows that let in natural light. The upper level bedrooms are all spacious with either a walk in closet or double closets. Primary bedroom is massive in size with a cathedral ceiling, 3 walk in closets, large sitting area, primary bathroom with tile, soaking tub, shower, dual sinks, and water closet with a window. The walk-out lower level offers a full bathroom, a partially finished recreation room (exposed but painted ceilings), and a wonderful workshop with benches and a ventilation system. HVAC with propane heat backup on the main level, and a propane water heater. The property really is a hidden gem.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,710
Status:
Active
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:
Active
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:
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. Our brokerage utilizes advanced technology and innovative marketing tools to showcase our listings. Select photos have been virtually staged to help buyers envision the home's full 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. Potential for 5th and 6th bedrooms! The basement includes two unfinished rooms offering the opportunity for future expansion and customization. **For RENT TO OWN Option need 10% option fee

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!

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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

    68
    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