Leonardtown MD Real Estate & Homes for Sale

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Beds:
5
Baths:
6.00
Sq.Ft.:
4,145
Status:
NEW LISTING
MLS#:
MDSM2034394
Type:
Single Family-Detached
Subdivision:
TOWER HILL
Lot size:
7 Acres
Year built:
1976
Courtesy: Century 21 Redwood Realty 301-208-2288
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ADDITIONAL INFORMATION

Stunning Potomac Riverfront Property – 7 Acres of Privacy and Possibility! Enjoy breathtaking panoramic views and spectacular sunsets from this beautiful 7-acre property along the Potomac River, featuring nearly 500 feet of river frontage protected by stone riprap. This private and peaceful setting offers a rare opportunity to own a substantial piece of waterfront property and make it your own. The main home features an open floor plan, sunroom, 3 bedrooms, 3½ baths, a large attached garage, and an oversized laundry/pantry room. The home needs updating and some renovation, but is priced to sell AS IS, offering tremendous potential to create your dream riverfront retreat in Southern MD. (main house has 3000 sq ft, apartment has 1040) A wonderful bonus is the detached 40' x 26' garage with a fully equipped apartment above, featuring 2 bedrooms and 2 full baths. The apartment has its own separate septic system and private driveway, making it ideal for temporary living while renovating the main home, guest accommodations, or additional living space. Enjoy a tranquil, secluded setting where you can enjoy the beauty of the Potomac River and unforgettable sunset views!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,292
Status:
NEW LISTING
MLS#:
MDSM2034570
Type:
Single Family-Detached
Subdivision:
MEADOWS AT TOWN RUN
Lot size:
0.21 Acres
Year built:
2020
Courtesy: Douglas Realty, LLC 410-255-3690
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ADDITIONAL INFORMATION

This is the home you've been waiting for. This Energy Star, Lancaster model home by QBH is loaded with upgrades. Over 3000 square feet of finished luxury living space, with additional square footage to add your touches to in the lower lever. The home boasts a large open living area with beautiful views of your private back yard and extended views of local farm land. Additionaly the main level has a spacious office/den area with glass french doors for privacy, large formal dining area and a mud room between the garage and kitchen with storage for shoes, coats, and kids sports equipment. The kitchen has ample high end cabinets, large island/breakfast bar all covered in granite. A double oven and gas cook top make cooking a dream. And lets not forget the huge pantry filled with shelving for storage. Upstairs, the primary retreat features a spa-like ensuite bath with two sinks, a large walk in shower and a huge soaking tub. There are three additional generous bedrooms, a full guest bath, and a dedicated laundry room. The finished basement adds excellent versatility with a bedroom and full bath, leaving a massive flexible space ready for your personal touch. Step outside to your own private oasis for relaxation or fun and games. An underground sprinkler system keeps your lawn and gardens happy and healthy, and a fully fenced rear yard with a deck provides room for cookouts, lawn games or a great space for your pets to enjoy. Dual HVAC units, a tankless water heater, premium trim, energy-efficient windows and appliances add to the comfort and low utility bills year-round. Garage is equipped with an EV charging system. Minutes from down town Leonardtown and an easy location to commute anywhere. Don't miss this rare turnkey opportunity!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,400
Status:
NEW LISTING
MLS#:
MDSM2034290
Type:
Single Family-Detached
Subdivision:
SAINT ANDREWS ES
Lot size:
11.32 Acres
Year built:
2024
Courtesy: Infinitas Realty Group 240-925-2224
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ADDITIONAL INFORMATION

Discover an exceptional investment opportunity in the heart of the sought-after Saint Andrews ES subdivision. This stunning ranch-style home, built in 2024, combines modern design with timeless farmhouse charm, making it a prime candidate for both rental income and long-term appreciation. Spanning over 11.32 acres, this property offers ample space for outdoor activities and potential expansion. The detached structure features three spacious bedrooms and two full bathrooms, providing a comfortable living environment for tenants or future homeowners. The unfinished basement with walkout stairs presents a blank canvas for additional living space, storage, or even a rental suite, enhancing your investment potential. Crafted with durable vinyl siding, this home is designed for low maintenance, ensuring that your investment remains protected and profitable. The expansive lot allows for various possibilities, from creating a serene outdoor retreat to exploring agricultural ventures, appealing to a wide range of potential renters or buyers. With no pool to maintain, your focus can remain on maximizing returns. The property's strategic location within a growing community ensures a steady demand for rental properties, making it an ideal addition to your investment portfolio. Seize the chance to own a piece of this promising market, where luxury meets opportunity. This property is not just a home; it's a gateway to financial growth and stability. Don't miss out on this unique investment opportunity!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,430
Status:
NEW LISTING
MLS#:
MDSM2034640
Type:
Single Family-Detached
Subdivision:
THE WOODS AT BAYSIDE
Lot size:
0.26 Acres
Year built:
2004
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

THIS IS IT!!! THE ONE YOU HAVE BEEN WAITING FOR! Welcome home to The Woods at Bayside in desirable Leonardtown, where charm, comfort, and beautiful updates come together in a home you are going to fall in love with! From the moment you pull into the driveway, this home just hugs you! The inviting front porch welcomes you in, and once you step inside, you'll see why this one is so special. This beautifully updated 3-bedroom, 2.5-bath colonial offers wonderful living space, a fantastic oversized kitchen with brand-new appliances, gorgeous LVP flooring, updated lighting, and so many thoughtful improvements throughout. And wait until you see the primary bedroom! Spacious, inviting, and complete with a HUGE walk-in closet that you are absolutely going to love! All of the bathrooms have been beautifully redone, giving the home a fresh, modern feel while keeping that warmth and character that makes a house feel like HOME. Outside, you'll appreciate the nice, level lot with room to relax, entertain, or simply enjoy your own outdoor space. Located in the sought-after Leonardtown area, you're close to shopping, restaurants, schools, and all the wonderful conveniences this community has to offer. And here's another reason to get excited! This home may qualify for 100% financing for eligible buyers! Imagine owning a beautifully updated home with little to no down payment required! There is just something about this house that makes you feel at home the minute you arrive. The updates, the space, the location, and that welcoming feeling you just can't put a price on. This is one you do NOT want to miss! Come see it for yourself and get ready to fall in love!

Beds:
5
Baths:
3.00
Sq.Ft.:
2,652
Status:
NEW LISTING
MLS#:
MDSM2034412
Type:
Single Family-Detached
Subdivision:
SOCIETY HILL
Lot size:
0.77 Acres
Year built:
1993
Courtesy: Century 21 Redwood Realty 301-208-2288
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ADDITIONAL INFORMATION

Welcome to sought-after Breton Bay, just minutes from the heart of Leonardtown! This spacious five-bedroom home sits on a generous .77-acre lot and offers the perfect blend of comfort, functionality, and neighborhood amenities. Enjoy the charm of a wraparound front porch, a maintenance-free deck, and a large, level backyard with plenty of room to relax, entertain, and play. Inside, the first floor features luxury vinyl plank flooring throughout most of the living spaces, with ceramic tile in the upgraded kitchen, complete with an island. The versatile layout includes a formal dining room, a dedicated office, an additional living room, and a step-down family room, providing plenty of space for everyday living and entertaining. A convenient mudroom and laundry room add to the home's functionality. Upstairs, the spacious primary suite features luxury vinyl plank flooring and a deluxe en-suite bath with ceramic tile floors, a walk-in shower, and a separate soaking tub. Four additional generously sized bedrooms and a full hall bath complete the upper level, offering plenty of room for family, guests, or additional workspace. Enjoy the Breton Bay lifestyle with access to neighborhood beach area and the clubhouse, along with pool membership available for an additional fee. With its spacious floor plan, expansive level lot, and convenient location near Leonardtown's shops, restaurants, and local amenities, this home offers a wonderful opportunity to enjoy Southern Maryland living at its best!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,348
Status:
NEW LISTING
MLS#:
MDSM2034440
Type:
Single Family-Detached
Subdivision:
ESTATES AT SINGLETREE
Lot size:
0.23 Acres
Year built:
2017
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

With a little Tender Loving Care, this 3300 plus sq ft home can be your castle! Custom built in 2017, the home is located in a highly regarded Leonardtown subdivision. First floor living space is highlighted by recessed lighting, two-story ceilings with exposed beams, and a fireplace with a repurposed mantel from a St. Mary's County barn. The kitchen of light gray cabinets, quartz counters, breakfast bar, and a large center island w/granite top island, is open to the large living space. Off to the side is a wet bar and a spacious walk-in pantry. First floor primary bedroom with cathedral ceilings, his and her walk-in closet with sliding barn door, and a primary bath featuring a long double vanity w/granite countertops, large shower and space for a designer tub. Primary bedroom also has its own access to the massive covered back porch. First floor spacious laundry room and access to the two car garage. Front door access showcases a walk-in coat closet and a convenient half bath next to the wooden staircase to the second level that reveals a nice size family room with a walk-in storage closet. Additionally there are two large bedtooms with walk-in closets that share a Jack-n-Jill bath with granite counter tops. The third second level bedroom has it own bath!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,092
Status:
Active
MLS#:
MDSM2034526
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.5 Acres
Year built:
1949
Courtesy: HomeZu 855-885-4663
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ADDITIONAL INFORMATION

Welcome to 22231 Bayside Road in Leonardtown, MD! This beautifully remodeled 3-bedroom, 2.5-bath home is move-in ready and packed with updates! Featuring a brand-new kitchen, new flooring throughout, and a new HVAC system, this home offers modern comfort with a fresh, inviting feel. The updated kitchen provides a beautiful space for cooking and entertaining, while the spacious pantry offers plenty of additional storage. With three generously sized bedrooms, two full bathrooms, and a convenient half bath, the layout provides both comfort and functionality for everyday living. Enjoy the peace of mind that comes with major updates already completed! Conveniently located in Leonardtown with easy access to shopping, dining, schools, and local amenities. Don't miss your opportunity to own this beautifully renovated home.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,568
Status:
Active
MLS#:
MDSM2034126
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
1.27 Acres
Year built:
1989
Courtesy: RE/MAX Realty Group 301-884-9493
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ADDITIONAL INFORMATION

All offers due by noon on Nov 12. Are you looking for a home in Leondardtown (Brenton Bay/Society Hill) with no HOA and space to stretch out? Discover the charm of this beautiful Colonial-style home, nestled on a generous 1.27-acre lot. Built in 1989, this inviting residence features 3 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and comfort. The well-designed layout offers a seamless flow between living areas, perfect for both entertaining and quiet evenings at home. Enjoy the convenience of an attached garage with front entry, ensuring easy access and additional storage. There is also a dedicated spot for an RV with power hook ups. The serene outdoor space invites you to unwind, with a fenced in yard, plenty of room for gardening, play, or simply soaking in the tranquility of nature. This home is not just a place to live; it's a sanctuary where memories are made. Embrace the opportunity to make this your dream home in a peaceful setting, all while being just a short drive from local amenities. This home has a lot of recent updates to include new siding, roof and chimney cap in April 2022, a sliding glass door in March 2022, new french doors in June 2023, a custom shed in 2024, a new front door and garage door this year, and brand new carpet that has never been lived in. Don't miss your chance to make this home your own!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,056
Status:
Active
MLS#:
MDSM2034514
Type:
Single Family-Detached
Subdivision:
BRETON BAY
Lot size:
0.87 Acres
Year built:
1962
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Charming Rancher in the Desirable Breton Bay Community! Opportunity awaits with this 2-bedroom, 1.5-bath ranch-style home situated on a spacious lot in the sought-after Breton Bay community. Conveniently located near Breton Bay Golf Course and the community beach, this property offers a wonderful setting with plenty of potential. Home is sold AS-IS Several major improvements have already been completed, including a new roof, new heat pump, new electrical panel, and new washer dryer providing a great starting point for future updates. With a little TLC and your personal touches, this home could truly shine! Whether you're looking for a primary residence, weekend retreat, or investment opportunity, this property offers an excellent chance to make it your own. Bring your vision and discover the possibilities in Breton Bay!

Beds:
5
Baths:
3.00
Sq.Ft.:
2,601
Status:
Active
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:
Active
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
View additional info

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:
Active
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

Your own 128.07-acre farm, minutes from historic Leonardtown. Open fields, woods, a private pond, and a stream surround an updated farmhouse, with the space to run nearly any farm, homestead, or hobby. The 4,395 sq ft rambler has 4 bedrooms and 3 baths, two fireplaces, and a new roof. A kitchen upgraded with commercial anppliances upstairs and a second kitchen area downstairs is great for gatherings, guests, or multigenerational living. Outbuildings this good are hard to find. There’s a detached garage and barns, plus garage/shop with heavy-duty 2-post lift for tractors and trucks. The land offers cleared fields, wooded acreage, and hunting. Heat pump with natural gas, well, and septic. RPD zoning. Cash, Conventional, Farm Credit, and USDA financing accepted. Close to Leonardtown shops, dining, and the wharf, and convenient to NAS Patuxent River. Farms this size with these improvements rarely come up in St. Mary’s County. Schedule your private tour today.

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
View additional info

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

Welcome home to a beautifully refreshed Leonardtown property offering the updates buyers want and the outdoor space they've been looking for! The custom kitchen steals the show with gorgeous 42-inch cabinetry, granite countertops, stainless steel appliances, and a farmhouse sink overlooking the backyard. Fresh paint, updated lighting, refreshed flooring, and an upgraded fireplace create a comfortable, move-in-ready feel. Outside, enjoy the new stamped concrete patio and walkways, a spacious corner lot, and room to relax, entertain, and enjoy the Breton Bay lifestyle. Best of all? NO HOA, with access to the community beach, dock, playground, and picnic amenities!

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
View additional info

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
View additional info

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
View additional info

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:
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.

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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

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.



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

    $477,450
    12.7%
    change since last quarter
  • # Active listings

    73
    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