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Leonardtown MD Real Estate & Homes for Sale

21 Properties Found

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$589,000

43641 Redmond Road Leonardtown, MD 20650

MLS: MDSM2029078 Photos
Beds:
n/a
Baths:
Sq.Ft.:
2,184
Status:
NEW LISTING
MLS#:
MDSM2029078
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
8.43 Acres
Year built:
1974
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

This great 8+ acre property with scenic pasture views. Solid 4 bedroom rambler on full basement. So many possibilities.

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$639,999

41377 Doctors Crossing Road Leonardtown, MD 20650

MLS: MDSM2029722 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,724
Status:
NEW LISTING
MLS#:
MDSM2029722
Type:
Single Family-Detached
Subdivision:
Clark's Rest
Lot size:
0.22 Acres
Year built:
2016
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Keller Williams Realty/Lee Beaver & Assoc. 703-330-2222
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ADDITIONAL INFORMATION

Welcome Home! 41377 Doctors Crossing Rd is a well-maintained home located in the sought-after Clark’s Rest community — where comfortable living meets a vibrant neighborhood lifestyle, with a pond just steps away and walking distance to the clubhouse. Offering 5,538 total square feet, including 3,724 finished square feet above grade, this home provides the space and flexibility. As you step through the front door, you’re welcomed by a beautiful two-story foyer and 9-foot ceilings that immediately create a sense of openness and natural light. The main level features a bedroom and a full bathroom, perfect for guests, multigenerational living, or a private home office. This flexible space adds everyday convenience and is a feature many buyers actively look for but rarely find. Moving through the home, the generous living areas provide plenty of room for both everyday life and entertaining. Picture family dinners, weekend gatherings, and cozy evenings in spaces designed to bring people together while still allowing everyone room to spread out. Imagine daily meals, morning coffee accompanied by a serene, wooded view—a private, lush backdrop where you can watch your loved ones playing, sledding down a snowy hill just steps from your backyard. Upstairs, you’ll find 4 spacious bedrooms throughout, including a massive primary suite that truly feels like a private retreat. With plenty of room for a king-size bed and a sitting area, it’s the perfect place to unwind at the end of the day. The primary bathroom offers ample space for daily routines and relaxation. Another upstairs bedroom features its own private bathroom, ideal for guests or anyone who appreciates extra privacy. All additional bedrooms are generously sized, offering comfort and flexibility for family members, hobbies, or work-from-home needs. The unfinished basement with rough-in plumbing provides 1,814 square feet of future potential. Whether you envision a recreation room, home gym, theater, or an additional bedroom, the groundwork is already in place to expand as your needs grow. Step outside and the lifestyle continues. A peaceful pond just steps from the front door offers the perfect setting for morning walks or relaxing evening sunsets. Living in Clark’s Rest means enjoying exceptional community amenities, including a clubhouse, two swimming pools with a shaded kiddie pool, multiple playgrounds, tennis courts, basketball court, volleyball area, and two gravel nature trails. Throughout the year, the community hosts pool opening and closing parties, holiday celebrations, and neighborhood events that bring neighbors together and create a welcoming atmosphere. Don’t wait — schedule your showing today! 41377 Doctors Crossing Rd is ready to welcome you home. ???

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$315,000

22204 Nomoni Street Leonardtown, MD 20650

MLS: MDSM2029298 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,008
Status:
NEW LISTING
MLS#:
MDSM2029298
Type:
Single Family-Detached
Subdivision:
St Clements Shores
Lot size:
0.18 Acres
Year built:
1930
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

Welcome to this bright and inviting home with an open-concept layout perfect for everyday living and entertaining. The spacious living area flows into the kitchen, featuring stainless steel appliances and convenient stackable washer and dryer access. Relax in the sunroom with a partial bay view and plenty of natural light. The primary suite offers a private en-suite bathroom, while an additional bedroom and full hall bath provide flexible living space. Outside, enjoy a curved stone porch where you can watch sunsets over the bay and a large shed for extra storage. Located in a water access neighborhood close to shopping and dining, this single-level, low-maintenance home is move-in ready. Mortgage savings may be available for buyers of this listing.

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$579,900

20260 Hawks Way Leonardtown, MD 20650

MLS: MDSM2029728 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,500
Status:
NEW LISTING
MLS#:
MDSM2029728
Type:
Single Family-Detached
Subdivision:
Hawks Nest
Lot size:
1.34 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

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

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$809,900

40737 Bobwhite Lane Leonardtown, MD 20650

MLS: MDSM2029030 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
5,454
Status:
NEW LISTING
MLS#:
MDSM2029030
Type:
Single Family-Detached
Subdivision:
Avenmar
Lot size:
3.62 Acres
Year built:
2001
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Avenmar beauty situated on over 3.5 acres, offering exceptional space and privacy. The custom kitchen features top-of-the-line appliances, custom cabinetry, solid-surface countertops, and stunning light fixtures. The main level includes formal dining and living rooms, a dedicated office space, and a two-story family room with an overlook from above. Floor-to-ceiling windows showcase peaceful wooded views, and a gas fireplace anchors the family room with warmth and style. The second level offers a spacious primary suite with a separate sitting room and an ensuite bath. Three additional bedrooms share a beautifully updated full bath featuring custom tile and cabinetry. A conveniently located laundry room is also on the bedroom level. A back staircase off the kitchen provides easy access to both sides of the second floor. Outdoor living shines with a new composite deck off the back, while the welcoming front porch overlooks the expansive front yard. The walk-out basement includes a finished full bath, with the remaining space ready for the new owner to customize. A Tesla solar roof adds energy efficiency and modern appeal.

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$674,900

44545 Brewer Lane Leonardtown, MD 20650

MLS: MDSM2029400 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
3,243
Status:
NEW LISTING
MLS#:
MDSM2029400
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
2.65 Acres
Year built:
2011
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

This beautiful custom rambler sits on over 2.5 peaceful acres, offering plenty of privacy and space. A welcoming circular driveway and a covered front porch greet you as you arrive, setting a relaxed tone right from the start. Inside, you’ll find thoughtful details throughout: 6-inch custom trim, wide 36-inch doorways, lots of natural light, and 9-foot ceilings that give the home an open, comfortable feel. Engineered cypress hardwood floors add warmth and durability underfoot. The kitchen is well-designed and practical, featuring solid hardwood cabinets, beautiful corian countertops, polished tiled backsplash, a large center island, good pantry space, and an eat-in area with room for a big table. It opens nicely into the family room, where a woodstove creates a cozy gathering spot. A separate office/den provides a quiet place to work or unwind. One side of the home has 3 spacious bedrooms, all with walk-in closets; with one having its own full bathroom for added convenience. On the opposite side is the primary suite, complete with an en-suite bathroom offering dual vanities, a soaking tub, a ceramic-tiled shower, and his & her walk-in closets. Do you love to have accessible storage? The walk-in attic space is convenient and amazing.! Step out back to the screened porch that overlooks a newer deck, firepit area, and wooded backdrop—perfect for relaxing or enjoying the outdoors. There’s also a bonus room above the garage with custom built-ins given additional space for extra flexibility. You’ll appreciate the oversized 2-car attached garage plus a separate 24x24 detached garage/workshop, giving plenty of room for vehicles, tools, or hobbies. A well-built, single-level home with thoughtful features and a calm, private setting—ready for its next chapter!

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$590,000

21117 Catnip Court Leonardtown, MD 20650

MLS: MDSM2029578 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,526
Status:
Active
MLS#:
MDSM2029578
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
1.38 Acres
Year built:
2003
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

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

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$437,000

41516 Marwood Circle Leonardtown, MD 20650

MLS: MDSM2029470 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
2,402
Status:
Active
MLS#:
MDSM2029470
Type:
Townhouse
Subdivision:
Clark's Rest
Lot size:
0.05 Acres
Year built:
2020
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

Professional photos coming soon. Welcome home to Marwood Circle in the desirable Clark's Rest Neighborhood of Leonardtown. This nearly new townhome built in 2020 has over 2400 square feet of living space and is in move in condition. Nice open concept on the main level includes an updated kitchen with granite countertops and island, stainless appliances and pantry, large family room, separate dining area and half bath. On the upper level you will find the spacious primary bedroom with en-suite bath, two spare bedrooms, full bath and upstairs laundry for added convenience. The fully finished lower level includes a nice rec room/office/craft room with full bath. The two car garage is spacious with extra driveway parking as well. An all composite deck is off the kitchen for grilling and entertaining. The neighborhood has a nice community clubhouse which can be used by residents for parties, etc, large community pool, basketball and tennis courts and tot lot. Close to historic downtown Leonardtown where you will find numerous restaurants, quaint shops and the Leonardtown Wharf to explore. There is also a free trolley in the summer and for special downtown events on the square which has a convenient stop right within the neighborhood. Schedule your appointment today!

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$474,900

22343 Newtowne Neck Road Leonardtown, MD 20650

MLS: MDSM2029528 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
2,114
Status:
Active
MLS#:
MDSM2029528
Type:
Single Family-Detached
Subdivision:
Leonardtown
Lot size:
1 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 443-968-9595
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ADDITIONAL INFORMATION

MOVE-IN READY!! Welcome to this beautifully maintained 4-bedroom, 2-bath rambler situated on a 1-acre lot in Leonardtown, Maryland. Offering the ease of one-level living and a functional, flowing floor plan, this home combines space, comfort, and practicality in a peaceful Southern Maryland setting. Step inside to find a spacious living room with gleaming floors and abundant natural light. The kitchen features stainless steel appliances, ample cabinetry, and generous counter space, opening conveniently to the dining area with French doors leading to the rear deck—perfect for entertaining or enjoying the wooded backdrop beyond the fully fenced back yard. All four bedrooms are generously sized, including a large primary suite with a private bath. The secondary bedrooms offer flexibility for guests, home offices, or hobbies. Storage is abundant throughout, highlighted by an impressive oversized pantry room complete with built-in shelving—ideal for bulk storage, small appliances, or organized household essentials. Additional features include a separate laundry room, utility space, attached 2-car garage, and plenty of room to spread out both inside and out. The 1-acre lot provides privacy while still being conveniently located near downtown Leonardtown, schools, shopping, and commuter routes. If you’re looking for space, storage, and single-level living in St. Mary’s County, this Leonardtown rambler checks all the boxes.

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$449,900

Lot 99 - 23725 Dragonfly Lane Leonardtown, MD 20650

MLS: MDSM2029488 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2029488
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Homesite #99 Madison D3: ****ALMOST READY FOR MARCH DELIVERY***Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,604 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, brushed nickel fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard—perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds—all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

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$449,900

Lot 101 - 23713 Dragonfly Lane Leonardtown, MD 20650

MLS: MDSM2029486 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2029486
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Homesite #101 Madison D3: ***ALMOST READY FOR MARCH DELIVERY***Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,604 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, brushed nickel fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard—perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds—all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

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$690,000

41438 Silver Charm Court Leonardtown, MD 20650

MLS: MDSM2029268 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,180
Status:
Active
MLS#:
MDSM2029268
Type:
Single Family-Detached
Subdivision:
Leonards Grant
Lot size:
0.45 Acres
Year built:
2010
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Tucked away at the end of a quiet cul-de-sac in sought-after Leonard’s Grant, this stately brick-front home offers space, upgrades, and an exceptional setting on nearly half an acre. Step inside to a spacious, well-designed layout featuring a private first-floor office—ideal for working from home. The upgraded kitchen serves as the centerpiece of the home. There is ample cabinetry, a double door pantry, nice prep space, and a butler’s pantry with a built-in wine rack, perfect for entertaining and everyday convenience. Upstairs, the expansive primary suite provides a true retreat with a massive walk-in closet, while the additional bedrooms are all generously sized, offering comfort and flexibility for family or guests. The fully finished basement adds even more living space, featuring a dedicated theater area, a 5th bedroom, and a full bath—perfect for guests or extended stays. A versatile utility room is currently being used as a dance studio, and there is still plenty of unfinished storage space. Outdoor living is just as impressive, with a large composite deck overlooking the nearly half-acre backyard, plus a custom paver patio with a built-in fire pit—ideal for relaxing evenings or hosting gatherings. Additional features include a radon mitigation system already in place and a prime location within the community. Enjoy all that Leonard’s Grant has to offer, including a pool, clubhouse, playgrounds, and more—all just minutes from Leonardtown’s shops, restaurants, and waterfront.

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$449,900

Lot 100 - 23719 Dragonfly Lane Leonardtown, MD 20650

MLS: MDSM2029208 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
2,571
Status:
Active
MLS#:
MDSM2029208
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.05 Acres
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Homesite 100 Madison D1: *** Mid March Delivery***Builder Incentive $12,500 in Closing Help with use of Preferred Lender & Title. Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level townhome offering 2,571 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with white kitchen cabinets, Quartz countertops, subway tile backsplash, black fixtures, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard, perfect for outdoor entertaining. Upstairs, retreat to the owner’s suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient laundry room complete the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds—all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

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$479,900

Lot 102 - 23707 Dragonfly Lane Leonardtown, MD 20650

MLS: MDSM2029202 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2029202
Type:
Townhouse
Subdivision:
Meadows At Town Run Ii
Lot size:
0.08 Acres
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

Homesite 102 Oakley D1*** Late March Delivery***Builder Incentive $12,500 in Closing Help with use of preferred lender and title company. New Construction – Oakley D1 End Unit at Meadows at Town Run II 2,966 Sq Ft 4 Bedrooms 3.5 Baths 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The first floor level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bath and access to your fenced backyard, ideal for guests, a private office, or a second living space. The oversized one-car garage and wide driveway provide ample parking and storage options. Upstairs, you'll find 9’ ceilings, luxury vinyl plank flooring, and a beautifully appointed kitchen with 42” upgraded maple cabinetry, slide-out dovetail drawers, soft-close features, and quartz countertops. The large center island, walk-in pantry, stainless steel GE appliances, and open-concept layout make this a true entertainer’s dream. The adjoining dining and family rooms lead out to a 14x12 maintenance-free deck overlooking your vinyl-fenced backyard. The upper level includes a luxurious owner’s suite with a tray ceiling, walk-in closet, and ensuite bath featuring dual vanities and QBHI’s signature deluxe tiled shower with bench, dual showerheads, and recessed lighting. Two additional bedrooms, a full hall bath, and a separate laundry room complete the top floor. Additional highlights include: finished and painted oversized garage, smart home technology with touchscreen IQ Pro command center, Skybell video doorbell, and smart thermostat, sodded and landscaped yard, stone-to-grade front, concrete front porch, and seamless gutters, 6’ vinyl fenced backyard with gate. Community amenities include clubhouse, pool, playground, tennis courts, and pickleball courts. Photos shown are representative and intended to illustrate a similar finished townhouse.

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$515,000

22547 Landing Way Leonardtown, MD 20650

MLS: MDSM2029148 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
2,764
Status:
Active
MLS#:
MDSM2029148
Type:
Townhouse
Subdivision:
Leonardtown Landing
Lot size:
0.05 Acres
Year built:
2005
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the community park. Everything is right where you need it in this lovely home. A must see.

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$779,900

22393 Saint Clements Avenue Leonardtown, MD 20650

MLS: MDSM2029036 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
2,097
Status:
Active
MLS#:
MDSM2029036
Type:
Single Family-Detached
Subdivision:
St Clements Wood
Lot size:
0.19 Acres
Year built:
1966
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: ListWithFreedom.com 855-456-4945
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ADDITIONAL INFORMATION

Experience refined waterfront living in this completely renovated rancher overlooking Saint Clements Bay. Originally built in 1966, this residence has been thoughtfully reimagined from top to bottom with extensive structural, electrical, and plumbing upgrades, blending modern luxury with effortless coastal charm. Situated on a waterfront lot, the property offers its own private L-shaped pier—perfect for boating, fishing, or simply enjoying peaceful bay views. The pier measures 91’ x 5’ with a 26’ x 10’ extension and approximately 7 feet of water depth to the decking, complete with a pier shed and brand new stairs leading from the home. The open-concept design welcomes you with sweeping water views the moment you step inside, creating a seamless connection between indoor and outdoor living. This home features 4 bedrooms, 2 full bathrooms, and 2 half bathrooms, offering both comfort and versatility. The primary suite serves as a private retreat with two closets and a spa-inspired bathroom featuring an oversized walk-in shower and double-sink vanity. High-end finishes flow throughout, including brand new engineered hardwood flooring in the main living areas, plush carpet in three bedrooms, and porcelain tile in three bathrooms. The designer kitchen is equipped with brand new quartz countertops, a gas stove with vent hood, refrigerator, dishwasher, wine cooler, and a dedicated coffee and wine bar area—ideal for entertaining or everyday enjoyment. Sliding glass doors and expansive windows frame stunning water views and fill the home with natural light. Outdoor living is elevated with a brand new waterfront deck, fresh siding on the sides and rear, a painted brick front, and a new front door, all enhancing curb appeal and durability. Major system updates include a brand new central AC and heating system, brand new gas water heater, an original heat pump serving the den addition, oil heat, and a fully improved crawl space with a new vapor barrier. The roof was replaced in 2009, along with new double-pane vinyl windows that fold in for easy cleaning. Additional highlights include two sheds, ample interior storage, and two on-property parking spaces. An optional, low-annual civic association fee provides access to picnic and swimming areas, boat ramps, and a playground. Conveniently located just an 11-minute drive to Leonardtown Square, offering a vibrant mix of shopping, dining, waterfront parks, historic charm, and year-round community events. This exceptional waterfront property offers a rare opportunity to enjoy modern luxury, private pier access, serene bayfront living, and close proximity to one of Southern Maryland’s town centers.

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$415,000

40736 Center 40 Circle Leonardtown, MD 20650

MLS: MDSM2028808 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
1,829
Status:
Active
MLS#:
MDSM2028808
Type:
Single Family-Detached
Subdivision:
Breton Bay Estates
Lot size:
0.51 Acres
Year built:
1965
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: CENTURY 21 New Millennium 301-862-2169
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ADDITIONAL INFORMATION

BACK ON MARKET. Charming Split Level home on just over 1/2 an acre in Breton Bay. As you enter the front door, the hardwood floors lead you throughout the main living areas of the home. Living room and dining room are both located on the main level. Kitchen with updated Corian counters and stainless appliances. Back door off kitchen opens to patio and back yard. Great entertaining space or space to relax and enjoy a cocktail. Primary bedroom with bathroom. Two additional bedrooms and a full hall bathroom complete the upper level. The lower level of the home has a rec room w/fireplace, half bathroom, laundry/utility room and outside access to the back yard. New holding tank is being installed. Located close to schools, shopping, and area amenities. Easy drive to downtown Leonardtown. Enjoy a round of golf, tennis or a swim in the pool by joining the Breton Bay Golf & Country Club. Schedule your online appointment today.

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$525,000

41635 Ferber Court Leonardtown, MD 20650

MLS: MDSM2028376 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,222
Status:
Active
MLS#:
MDSM2028376
Type:
Single Family-Detached
Subdivision:
Singletree
Lot size:
0.28 Acres
Year built:
2006
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Home Towne Real Estate 301-862-4000
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ADDITIONAL INFORMATION

Perfect Leonardtown Location near sought after schools and county services! Beautiful 2 story home situated on a professionally landscaped level lot with fully fenced back yard. Home is freshly painted and has newly installed carpet throughout main and upper levels. Roof and gutters were recently replaced in 2025. HVAC has been serviced annually. Upper level has 4bedrooms; 2 full bathrooms and laundry room. Main level consists of living room, dining room, family room with propane fireplace, kitchen with pantry and eating area, half bath, direct access to the 2-car garage, and access to backyard. Lower-level basement is accessed from inside and also has 6-foot-wide areaway leading to the level fully fenced backyard. Backyard is accessible from right side via 4-foot gate and on the left side via 8-foot gate. Home is located on cul-de-sac with easy short walk to all restaurants and shops in downtown Leonardtown, College of Southern Maryland, Saint Mary's Hospital and Leonardtown wharf. Excellent condition and ready to move-in. Basement currently has numerous weightlifting gear exercise caution during all showings.

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$599,950

22615 Washington Street Leonardtown, MD 20650

MLS: MDSM2028632 Photos
Beds:
n/a
Baths:
Sq.Ft.:
1,691
Status:
Active
MLS#:
MDSM2028632
Type:
Other
Subdivision:
Leonardtown Town Center
Lot size:
0.57 Acres
Year built:
1940
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Infinitas Realty Group 240-925-2224
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ADDITIONAL INFORMATION

Value is in the land. Unique opportunity in the heart of downtown Leonardtown. Property includes the Washington Street parcel with an additional rear parcel on Lawrence Avenue conveying, together forming an assembly of approximately one and a half acres within the Town of Leonardtown limits. Zoned within a residential district and located in an area recognized as part of Leonardtown’s Arts & Entertainment environment, this site offers flexibility for buyers with vision. Prior use history and prime location may support creative redevelopment concepts—buyers are encouraged to submit plans and ideas directly to the Town of Leonardtown for consideration. Ideal for those seeking a downtown setting close to the waterfront, shops, dining, and year-round community events. Whether envisioning a custom residence, small-scale residential development, or a thoughtfully designed project consistent with the surrounding neighborhood, this property presents a rare opportunity to shape a lasting presence in one of Southern Maryland’s most vibrant town centers. Property sold as-is. Hold Harmless Agreement required prior to viewing. Buyers to perform all due diligence regarding zoning, development potential, and Town approvals.

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$699,900

21345 Fairwood Court Leonardtown, MD 20650

MLS: MDSM2028586 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,080
Status:
Active
MLS#:
MDSM2028586
Type:
Single Family-Detached
Subdivision:
Leonardtown Farms
Lot size:
0.83 Acres
Year built:
2012
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX One 443-771-8009
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ADDITIONAL INFORMATION

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

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$624,900

40855 Spring House Lane Leonardtown, MD 20650

MLS: MDSM2028400 Photos
Beds:
5
Baths:
3.00
Sq.Ft.:
3,464
Status:
Active
MLS#:
MDSM2028400
Type:
Single Family-Detached
Subdivision:
Breton Bay Estates
Lot size:
0.4 Acres
Year built:
1978
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Berkshire Hathaway HomeServices PenFed Realty 410-394-0990
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ADDITIONAL INFORMATION

Here is a rare incoming-generating opportunity in Breton Bay – a waterfront community surrounding a beautiful golf course. Maximize your investment with this unique 3,464 sq. ft. residence, well designed to function as two distinct homes under one roof. Whether you are looking to "house hack" by offsetting your mortgage or seeking a turnkey multi-unit investment, this property offers a proven rental history that is hard to find. The secondary residence isn't just a suite; it’s a high-demand 2-bedroom, 1-bath apartment with a private exterior entrance, full kitchen, dedicated laundry, and its own private deck. With a track record of long-term stability—including a previous seven-year tenancy—this space provides immediate income potential in a high-demand area. The main residence is a contemporary styled home featuring vaulted ceilings, hardwoods, and a light-filled open concept. The cottage kitchen boasts custom cabinetry, a rolling island, and a storage closet this seller used as wine storage. The entire top level serves as a private owner’s sanctuary with an ensuite bath and walk-in closet, while two additional spacious bedrooms occupy their own dedicated level for maximum privacy. This home boasts a brand-new septic system installed in the Fall 2025, fresh paint throughout, and new carpet in both the home and the apartment. If it is not a rental income you are seeking, reimagine this home into two distinct living experiences under one roof—perfect for multigenerational families, a premium home office suite, or a high-end guest wing. Living in a waterfront community with a beach, pier, playground, and optional golf club membership. This can be more than a home; it may be a strategic financial move to allow the rental income to offset your mortgage. Let this property work for you!

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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

    $514,250
    12.7%
    change since last quarter

  • # Active listings

    24
    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

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