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Kim Briscoe
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Leonardtown MD Real Estate & Homes for Sale

44 Properties Found

The median home value in Leonardtown, MD is $540,000. This is higher than the county median home value of $325,000. The national median home value is $308,980. The average price of homes sold in Leonardtown, MD is $540,000. Approximately 60% of Leonardtown homes are owned, compared to 33% rented, while 7% are vacant. Leonardtown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Leonardtown real estate agent to arrange a tour today!
Learn more about Leonardtown Real Estate.


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Beds:
3
Baths:
3.00
Sq.Ft.:
3,016
Status:
NEW LISTING
MLS#:
MDSM2033518
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
26.62 Acres
Year built:
1956
Courtesy: O'Brien Realty ERA Powered
View additional info

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

Beds:
4
Baths:
4.00
Sq.Ft.:
4,246
Status:
NEW LISTING
MLS#:
MDSM2033536
Type:
Single Family
Subdivision:
LEONARDTOWN FARMS
Lot size:
0.85 Acres
Year built:
2011
Courtesy: EXP Realty, LLC
View additional info

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

Beds:
4
Baths:
3.00
Sq.Ft.:
2,624
Status:
NEW LISTING
MLS#:
MDSM2033362
Type:
Single Family
Subdivision:
SOCIETY HILL
Lot size:
0.34 Acres
Year built:
1980
Courtesy: Redfin Corp
View additional info

Breton Bay/Society Hill! Steps away and within view of the golf course. Desirable location within a sought after school zone. This community has water access to Breton Bay via community association (voluntary dues, No HOA). Affordability within a desirable location is hard to find so here's your change. This 2 story colonial style home has a large addition off the back of the home that features a spacious rec room, laundry/utility area, and pellet stove. Main level of this home has hardwood flooring, upper level is laminate plank. Primary bedroom has an attached full bathroom, and all 3 secondary bedrooms all have spacious walk-in closets. Updates have been made to both full bathrooms and the home is freshly painted. Enjoy the outdoors on the screened-in deck. Great, flat lot, mature landscaping and curb appeal. EV Charger in garage. This home has been very well-maintained! Walking distance to the community pier, playground & golf course. Don't miss your chance!

Beds:
5
Baths:
3.00
Sq.Ft.:
2,953
Status:
NEW LISTING
MLS#:
MDSM2033456
Type:
Single Family
Subdivision:
WHISPERING PINES
Lot size:
4.24 Acres
Year built:
2015
Courtesy: CENTURY 21 New Millennium
View additional info

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

Beds:
5
Baths:
4.00
Sq.Ft.:
5,534
Status:
NEW LISTING
MLS#:
MDSM2033428
Type:
Single Family
Subdivision:
AVENMAR
Lot size:
2.19 Acres
Year built:
2002
Courtesy: CENTURY 21 New Millennium
View additional info

Welcome to Avenmar, where this spacious home is situated on a beautiful lot of over two acres, offering privacy, mature trees, and a peaceful wooded setting. Built in 2002 and largely in its original condition, the home has been well maintained and is ready for its next owner to bring their own style and updates. The main level offers a spacious, open layout with a formal dining room, formal living room, private office, and full bath. The centerpiece of the home is the impressive two-story family room with a gas fireplace and floor-to-ceiling windows overlooking the trees and woods. The kitchen features Corian countertops, solid hardwood cabinetry, generous workspace, and an easy flow into the main living areas. Upstairs, front and rear staircases lead to a catwalk overlooking the family room below. The primary ensuite features a private bath and two generous walk-in closets. Three additional large bedrooms, a full bath, and convenient upper-level laundry complete this level. The fully finished walk-out lower level provides even more living space with a large recreation room, fifth bedroom, and full bath, making it ideal for guests, extended family, a home gym, or additional entertaining space. Avenmar offers an exceptional collection of community amenities, including access to Breton Bay with a community pier and kayak launch, clubhouse, swimming pool, tennis and volleyball courts, walking trails, horse stables, and equestrian trails. With over two acres, a private wooded setting, three finished levels, five bedrooms, multiple living and entertaining spaces, and access to Breton Bay, this property offers a great opportunity to update and personalize a substantial home in one of Leonardtown's most distinctive communities.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,964
Status:
NEW LISTING
MLS#:
MDSM2033354
Type:
Single Family
Subdivision:
VILLAGES AT LEONARDTOWN
Lot size:
0.29 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Baldus Real Estate, Inc.
View additional info

Discover a prime investment opportunity in the charming VILLAGES AT LEONARDTOWN! This stunning 4-bedroom, 2.5-bath Colonial home, built in 2004, boasts 2,774 sq. ft. of potential. With a spacious unfinished basement featuring walkout stairs and rough bath plumbing, you have the perfect canvas to create additional living space or rental units, maximizing your return on investment. The property sits on a generous 0.29-acre lot, offering ample outdoor space for future enhancements or landscaping. The attached 2-car garage and driveway provide convenience for tenants or future buyers. Located in a desirable community, this home is poised for appreciation, making it an ideal addition to your portfolio a solid structure of brick and vinyl siding, upkeep is minimal, allowing for a hassle-free investment. Seize this chance to invest in a property that combines comfort, potential, and value in a thriving neighborhood!

Beds:
5
Baths:
3.00
Sq.Ft.:
3,881
Status:
Active
MLS#:
MDSM2033166
Type:
Single Family
Subdivision:
AVENMAR
Lot size:
3.21 Acres
Year built:
2002
Courtesy: Metro City Realty
View additional info

Welcome to this beautiful brick-front home in the highly sought-after Avenmar Community of historic Leonardtown, Maryland. Situated on over 3 private acres and tucked away on a secluded road shared by only three other homes, this property offers the perfect balance of privacy, nature, and convenience. Freshly updated with a new roof, new carpet throughout, and fresh paint, this move-in-ready home features 4 bedrooms, 2.5 bathrooms, and overflows with charm and comfort. The spacious primary suite includes its own fireplace, a large walk-in closet, and an impressive ensuite bath with a Jacuzzi tub. A second fireplace in the family room creates a warm and inviting gathering space for 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. The upper-level laundry room comes complete with washer and dryer, while the unfinished walk-out basement offers endless potential for future expansion, recreation space, or storage. Additional features include a 2-car garage, mature landscaping with unique banana and bamboo plants, and a peaceful setting ideal for nature lovers. Beyond the home itself, Avenmar offers an unmatched 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.

Open House:

Sunday, 9/6 11:00-1:00PM

Beds:
4
Baths:
3.00
Sq.Ft.:
4,018
Status:
Active
MLS#:
MDSM2033246
Type:
Single Family
Subdivision:
CLARK'S REST
Lot size:
0.16 Acres
Year built:
2023
Courtesy: The Southside Group Real Estate
View additional info

Welcome to 41524 Fairwood Ct, Leonardtown, MD 20650! This inviting ranch-style home offers comfortable one-level living with a spacious, open-concept great room, dining area, and kitchen designed for everyday living and entertaining. The kitchen features a generous island and built-in pantry, while the convenient mudroom and first-floor laundry add functionality. The thoughtful layout includes two bedrooms with a shared bath, plus a private owner's suite featuring a spa-like shower and walk-in closet. The finished partial basement provides additional living space with a recreation room, full bath, and bedroom - perfect for guests, a home office, or additional entertaining space. A versatile floor plan, spacious living areas, and convenient features make this home a wonderful place to call home!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,873
Status:
Active
MLS#:
MDSM2033236
Type:
Single Family
Subdivision:
LEONARDS GRANT
Lot size:
0.64 Acres
Year built:
2011
Courtesy: Real Broker, LLC
View additional info

2.25% Assumable VA loan & one of the largest lots in Leonard's Grant at .64 acres! This brilliant Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Lots of fruit trees (Fig, Apple, Mulberry, Dwarf Peach, Pear, Strawberry and Persimmon). Enter to find gorgeous exotic hardwood tigerwood floors flowing seamlessly across the main level into the Kitchen where you will be invited to Andura Max floors. Screened porch to enjoy beautiful sunsets. The finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, the spare guest bedroom and a walk-out basement. Enjoy peace of mind with tankless hot water heater. Outside, the premium, fully fenced backyard boasts a 5-foot elegant black aluminum fence, offering a pristine and secure oasis for pets, play or relaxing. Firepit with relaxing patio. Don't miss this one-of-a-kind home in a fantastic location! Situated in the highly sought after Leonard's Grant neighborhood with tennis court, basketball court, community pool, large green, multiple playgrounds and recreation center. Within distance to Elementary School and very close to the amazing Leonardtown Square with restaurants, water views and shops.

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2033226
Type:
Townhouse
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.05 Acres
Courtesy: RE/MAX One
View additional info

*** November Delivery *** ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #143 Madison D3: Welcome to Meadows at Town Run.... Leonardtown's Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, black fixtures, white perimeter kitchen cabinets, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard...perfect for outdoor entertaining. Upstairs, retreat to the owner's suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient W/D on the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds...all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Open House:

Sunday, 9/6 11:00-4:00PM

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDSM2033224
Type:
Townhouse
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.05 Acres
Courtesy: RE/MAX One
View additional info

***** October Delivery ****** ***** Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #139 Madison D3: Welcome to Meadows at Town Run.... Leonardtown's Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,554 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus a versatile room that can function as a fourth bedroom, guest suite, or recreation room, complete with a full bath and closet. The main level boasts a spacious and open kitchen with Quartz countertops, black fixtures, white perimeter kitchen cabinets, a center island, large walk-in pantry, and breakfast nook. The open-concept family room flows seamlessly from the kitchen to a 14x12 maintenance-free deck overlooking a fenced backyard...perfect for outdoor entertaining. Upstairs, retreat to the owner's suite with tray ceiling, walk-in closet, and a luxurious Deluxe Signature Shower by QBHI featuring floor-to-ceiling tile, dual showerheads, a built-in seat, ledge, shelving niche, and recessed lighting. Two additional bedrooms, a full hall bath, and a convenient W/D on the upper level. Community amenities include sidewalks, a swimming pool, recreation center, pickleball and tennis courts, and playgrounds...all located in the heart of charming Leonardtown, Maryland. Come experience the unmatched quality and thoughtful design that sets Quality Built Homes apart. Schedule your tour today! Photos shown are representative and intended to illustrate a similar finished townhouse.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,430
Status:
Active
MLS#:
MDSM2033146
Type:
Single Family
Subdivision:
BRETON BAY
Lot size:
0.43 Acres
Year built:
1992
Courtesy: Infinitas Realty Group
View additional info

Welcome to 40611 Merion Court, Leonardtown, MD 20650! This stunning three-level Colonial offers the perfect blend of elegance, comfort, and resort-style living, ideally positioned with beautiful views backing directly to Breton Bay golf course. Featuring 4 bedrooms, 3.5 baths, and a fully finished basement, this home provides exceptional space for both everyday living and entertaining. The finished lower level includes a dedicated home theater and private office, while the screened-in back porch creates a wonderful outdoor retreat overlooking the manicured fairway and mature landscaping. Inside, you'll find a spacious and inviting layout designed for comfortable living, while the beautifully landscaped grounds provide privacy and a picturesque setting. The spacious primary suite is a true retreat, complete with a vaulted ceiling, private sitting room, generous walk-in closet, and a completely remodeled primary bathroom- showcasing gorgeous stonework and high-end finishes. Located in a sought-after community offering an impressive array of amenities, residents can enjoy access to a private pier, golf course, and swimming pool - bringing a vacation-like atmosphere right to your doorstep. Whether you're relaxing on the back porch, enjoying movie night in your private theater, working from home, or taking advantage of the community amenities, 40611 Merion Court offers the lifestyle you've been waiting for!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,218
Status:
Active
MLS#:
MDSM2032876
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.6 Acres
Year built:
1953
Courtesy: CENTURY 21 New Millennium
View additional info

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. Seller is offering a 1-year HSA home warranty.

Beds:
5
Baths:
3.00
Sq.Ft.:
1,080
Status:
Active
MLS#:
MDSM2033116
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.3 Acres
Year built:
2005
Courtesy: Century 21 Redwood Realty
View additional info

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

Beds:
4
Baths:
4.00
Sq.Ft.:
3,648
Status:
Active
MLS#:
MDSM2033062
Type:
Single Family
Subdivision:
ACADEMY HILLS
Lot size:
0.2 Acres
Year built:
2005
Courtesy: RE/MAX Realty Group
View additional info

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

Beds:
5
Baths:
4.00
Sq.Ft.:
4,176
Status:
Active
MLS#:
MDSM2032818
Type:
Single Family
Subdivision:
CLARK'S REST
Lot size:
0.21 Acres
Year built:
2019
Courtesy: CENTURY 21 New Millennium
View additional info

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,834
Status:
Active
MLS#:
MDSM2032956
Type:
Single Family
Subdivision:
HERRING CREEK ESTATES
Lot size:
0.84 Acres
Year built:
1970
Courtesy: CENTURY 21 New Millennium
View additional info

If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for entertaining guests or creating lasting memories with family and friends. This move-in-ready home features a new HVAC system, beautifully updated bathrooms, brand-new flooring throughout, an encapsulated crawl space, and countless additional upgrades that offer both comfort and peace of mind. Opportunities like this don't come around often - schedule your showing today before it's gone!

Beds:
5
Baths:
2.00
Sq.Ft.:
1,552
Status:
Active
MLS#:
MDSM2032950
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
4.12 Acres
Year built:
1986
Courtesy: Samson Properties
View additional info

Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road in Leonardtown, Maryland. Situated on more than four acres, this spacious five-bedroom, manufactered two-bath rambler offers a rare combination of comfortable one-level living, privacy and future possibilities. he generous homesite provides abundant room for outdoor recreation, gardening, equipment storage, animals or creating your own private retreat. The property may also appeal to builders, investors or buyers exploring potential subdivision or development opportunities, subject to county zoning, approvals, utilities and feasibility studies. Inside, the home offers a flexible five-bedroom layout with space for home offices, guest rooms, multigenerational living or hobby areas. Its rambler-style design provides convenient everyday living with minimal stairs. Located near historic Leonardtown, local shopping, dining, schools, medical facilities and Southern Maryland commuter routes, this property is ideal for buyers seeking acreage without sacrificing access to nearby amenities. Bring your vision and discover the potential of this distinctive Leonardtown property.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,388
Status:
Active
MLS#:
MDSM2032802
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
3.8 Acres
Year built:
2017
Courtesy: RMG Realty
View additional info

Nestled on a generous 3.8-acre corner lot, this charming Cape Cod-style home, built in 2018, offers a perfect blend of comfort and timeless appeal. With its excellent condition and thoughtful design, this residence is ready to welcome you home. Step inside to discover a warm and inviting interior that features a traditional floor plan, ideal for everyday living and entertaining. The home offers four well-appointed bedrooms, including a convenient entry-level bedroom, perfect for guests or those seeking single-level living. The primary suite features a walk-in closet and a spa-like bathroom complete with a soaking tub and a walk-in shower, providing a serene retreat at the end of the day. Additional interior highlights include plush carpeting, elegant hardwood floors, and ceiling fans that enhance comfort throughout the seasons. For those who appreciate technology, the home is equipped with a sound system, ensuring that your favorite tunes accompany you in every room. Outside, the property features a screened in porch, perfect for outdoor relaxation while enjoying the tranquility of your surroundings. The oversized detached garage offers ample space for vehicles and storage and has heat/ac, electricity and plumbing while complemented by a paved driveway for easy access. There is ample parking space for vehicles, campers, and more! Enjoy the peace of country living while being just a short drive from local amenities, shopping, and dining options. Don't miss the opportunity to make this beautiful residence your forever home!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,940
Status:
Active
MLS#:
MDSM2032698
Type:
Single Family
Subdivision:
BRETON BAY/SOCIETY HILL
Lot size:
0.56 Acres
Year built:
1972
Courtesy: Compass
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Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area and into the kitchen. The kitchen was completely renovated in 2025 and features quartz counters, soft close cabinetry, tile floors, and stainless appliances. There's plenty of storage and counter space for easy meal prep and entertaining. For the grilling enthusiasts, a screened porch is a few steps away from the kitchen making it convenient for grilling and outdoor dining. As you progress down the hall, you're greeted with two spacious bedrooms, and a hall bathroom that was renovated in 2024 with a timeless design. At the end of the hall is the generous sized owners bedroom, complete with multiple closets, a dressing area, and an ensuite bathroom that was also renovated in 2024 with a sleek, modern motif. The owners suite features a private covered deck overlooking the back yard and farm land, making it a quiet retreat for relaxing after a long day. The lower level is partially finished with a 4th bedroom, 3rd full bathroom, and spacious second family room. The family room enjoys a bar for entertaining, as well as access to the two car garage. The remaining lower level contains laundry, built-in storage cabinets, and tons of storage space! The heat pump was replaced in 2024, and the roof was replaced with 40 year shingles in 2010. A Mini Fridge in the basement bar and a refrigerator in the garage convey. This home is uniquely located in Breton Bay, and enjoys views of the golf course, and views of the farmland behind the home. It's also within walking distance to the Breton Bay Clubhouse, and a mere 7 minutes to downtown Leonardtown. The community enjoys a beach area and playground for a minimal annual fee. Membership to the Breton Bay Country Club grants access to the pool and tennis courts. Welcome Home!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,346
Status:
Active
MLS#:
MDSM2032660
Type:
Single Family
Subdivision:
VILLAGES AT LEONARDTOWN
Lot size:
0.35 Acres
Year built:
2005
Courtesy: Coldwell Banker Premier
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Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so much more just inside the walls! Outside the walls of the home, features a shed, fenced in backyard, a beautifully manicured lawn watered by an in-ground irrigation system and several flower beds for all a plant enthusiast could ever ask for! Situated in the subdivision known as The Villages at Leonardtown, we are only minutes from all the shops, dining, and attractions Leonardtown has to offer, with a further drive to all the shops, attractions, dining near Pax River Naval Base and the surrounding area offers. Come take a look at this home today!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,246
Status:
Active
MLS#:
MDSM2032510
Type:
Single Family
Subdivision:
LEONARDTOWN FARMS
Lot size:
0.85 Acres
Year built:
2011
Courtesy: EXP Realty, LLC
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Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of Leonardtown's most desirable neighborhoods. Tucked near the end of a quiet street by the cul-de-sac, this 4-bedroom, 3.5-bath home offers more than 3,500 square feet of finished living space, a fully finished basement, and an expansive backyard designed to be enjoyed. Step inside to a bright, welcoming floor plan with plenty of room for both everyday living and entertaining. At the heart of the home is the updated kitchen, featuring a large center island with built-in beverage refrigerator, beautiful finishes, and durable tile flooring that continues into the bumped-out breakfast area overlooking the backyard. Multiple living spaces throughout the main level make it easy to host a crowd while still feeling comfortable and connected. Outside is where this property really shines. The vinyl fenced, level backyard offers an incredible amount of usable space for pets, play, gardening, or gatherings. Enjoy summer dinners on the expansive deck, relax beneath the pergola-covered patio, or simply take in the privacy of your nearly one-acre lot. A large storage shed provides plenty of additional space for lawn equipment and outdoor gear. Upstairs, the oversized primary suite provides a relaxing retreat with a spacious walk-in closet and the added convenience of laundry hookups. Three additional generously sized bedrooms with ample closet space complete the upper level. The finished basement adds even more flexibility, featuring a large recreation area, full bathroom, bonus room perfect for an office, gym, playroom, hobby space, or guest area, plus unfinished storage space. A side-load two-car garage rounds out a home that was built for buyers who need room to spread out. Beyond the property itself, Fairwood Ct. offers the neighborhood atmosphere so many buyers are searching for - a place for evening walks, bike rides, backyard gatherings, and putting down roots. With 3,500+ finished square feet, 4 bedrooms, 3.5 bathrooms, a finished basement, nearly an acre of land, a fenced backyard, and an updated kitchen, 21395 Fairwood Ct. offers the space and versatility that can be difficult to find in Leonardtown. Come see how much this home has to offer.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,691
Status:
Active
MLS#:
MDSM2032426
Type:
Single Family
Subdivision:
LANEDON
Lot size:
0.46 Acres
Year built:
2005
Courtesy: Keller Williams Flagship
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Set on a level, open corner lot with a small view of the Potomac River - and best of all, **NO HOA** - this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features hardwood flooring throughout most of the space, installed in 2019. The kitchen is appointed with cherry cathedral-style cabinetry, Corian countertops, an L-shaped center island, an Americast sink, and indirect lighting above and below the cabinets. The full suite of stainless-steel appliances includes a refrigerator with ice and water in the door, range, dishwasher, and built-in microwave. Hardwood stairs with white risers and balusters connect the home's two levels. The foyer welcomes guests with 12-by-12-inch ceramic-marble tile and a fiberglass front door featuring sidelights and decorative leaded glass. The spacious primary bedroom includes a walk-in closet with a distinctive cedar ceiling. Its private bathroom offers a jetted soaking tub and separate shower. The second bedroom features luxury vinyl plank flooring, the third bedroom is carpeted, and the hall bathroom includes a tub-and-shower combination. Downstairs, the finished living area offers luxury vinyl plank flooring and a wood-burning fireplace surrounded by brick painted a stylish red. This level also includes a full bathroom with a tub-and-shower combination, a newer washer and dryer, and flexible space for relaxing, entertaining, working, or accommodating guests. The home is also wired for an alarm system. Outdoor living is a standout feature. A composite deck with vinyl pickets and handrails overlooks the fully fenced backyard, while the patio beneath the deck provides additional covered entertaining space. The backyard also includes a tiki-style entertainment area, a three-year-old 12-by-24-foot Intex above-ground pool, and a very large storage shed offering plenty of room for lawn equipment, tools, recreational gear, and seasonal items. Major improvements include the roof and hardwood flooring in 2019, HVAC in 2017, and water heater in 2015. Only two people have occupied the home since 2015, reflecting the light use and care it has received. With **NO HOA**, a level corner lot, an oversized garage, a blacktop driveway, abundant storage, extensive outdoor amenities, and a glimpse of the Potomac River, this home delivers the space and freedom to enjoy your property your way.

Open House:

Sunday, 9/6 11:30-3:30PM

Beds:
4
Baths:
3.00
Sq.Ft.:
2,976
Status:
Active
MLS#:
MDSM2032286
Type:
Single Family
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.23 Acres
Year built:
2026
Courtesy: RE/MAX One
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Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes' Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space. This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level is designed for everyday living with comfortable gathering spaces, an open flow, and room to make the home your own. Meadows at Town Run II is one of Leonardtown's newest opportunities, with only 12 single-family homes planned in this section. Enjoy convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Planned amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Estimated delivery 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. This is one of only 12 single-family homes to be built in Meadows at Town Run II, making it a rare opportunity in one of Leonardtown's most convenient communities. Enjoy close proximity to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers use QBHI's preferred lender and one of their trusted title companies. Quality Built Homes, Inc.'s model home at Meadows at Town Run II is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about Homesite 5, available selections, incentives, and delivery timing. Photos may show a previously built Bell model or similar QBHI home and are for example purposes only. Actual home, features, finishes, options, and selections may vary.

Open House:

Sunday, 9/6 11:30-3:30PM

Beds:
4
Baths:
3.00
Sq.Ft.:
2,701
Status:
Active
MLS#:
MDSM2032276
Type:
Single Family
Subdivision:
MEADOWS AT TOWN RUN II
Lot size:
0.23 Acres
Year built:
2026
Courtesy: RE/MAX One
View additional info

New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes' Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow. The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner's suite includes generous closet space and a private bath, with three additional bedrooms, a full bath, and convenient second-floor laundry. Estimated delivery 2027... final timing dependent on contract date, selections, permitting, and builder construction schedule. Builder incentive available! Quality Built Homes, Inc. is offering $15,000 in closing help when buyers use QBHI's preferred lender and one of their trusted title companies. Quality Built Homes, Inc.'s model home at Meadows at Town Run II is open Thursday through Sunday from 11 AM to 4 PM. Schedule an appointment today to learn more about Homesite 4, available selections, incentives, and delivery timing. Meadows at Town Run II is located in Leonardtown with convenient access to Duke Elementary, the Leonardtown Library, Downtown Leonardtown, shopping, dining, parks, and commuter routes. This section will include only 12 single-family homes. Planned community amenities include a Rec Center with game room, yoga studio, gym, common area, and pool to be built in 2027, plus tennis/pickleball courts and walking trails. Former decorated Mattingly model shown for example purposes only. Photos do not represent the actual home on Lot 4. Actual home, features, finishes, options, selections, and pricing may vary.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

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