67 properties for sale in Holly Oaks, District 3 Leonardtown St Mary's County Maryland

Incredible opportunity to own 1.86 acres of prime land! This property features an existing two-bedroom, one-bath rambler. Sold strictly AS-IS. Looking for a quick settlement!

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!

Pending*. Lot 151 New Construction Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland 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 3095 sq ft home offers generous living areas, abundant natural light, and the perfect blend of functionality and style. The main level welcomes you with a finished rec room or optional 4th bedroom, complete with a full bath and access to your backyardideal 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 granite countertops. The large center island, walk-in pantry, stainless steel GE appliances, and

Welcome Home to 26251 True Grit Ct, Mechanicsville, MD. This beautifully updated home is move-in ready and shows like new! Step inside to discover a freshly renovated kitchen featuring stunning quartz countertops and durable, stylish luxury vinyl flooring a perfect blend of elegance and everyday practicality. The main living areas showcase gorgeous refinished hardwood floors, complemented by a fresh coat of paint throughout that gives every room a crisp, clean, and welcoming feel. Practical upgrades add extra peace of mind, including a brand-new hot water heater, so you can settle in without worrying about major repairs. Outside, you'll find a true standout feature: a massive shed workshop, offering incredible space for hobbies, storage, a home business, or a dedicated workshop setup the possibilities are endless. With its combination of thoughtful updates and functional outdoor space, this Mechanicsville gem is ready to welcome its next owner. Schedule your showing today!

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 owners 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 bedroomperfect 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!

Beautifully maintained and thoughtfully updated, this spacious home offers over 3,800 finished square feet of versatile living space on a picturesque 1-acre lot. Built in 2013, this impressive residence features 5 bedrooms, 3.5 baths, and a 2-car garage, providing ample room for today's evolving lifestyles. The heart of the home is the inviting kitchen, featuring granite countertops, a center island, and an open layout designed for both everyday living and effortless entertaining. Beautiful hardwood floors grace the main level, while fresh paint, updated lighting, and brand-new wall-to-wall carpeting enhance the home's warm and welcoming atmosphere. The fully finished lower level offers exceptional flexibility with its own living area, kitchen, bedroom, full bath, laundry area with dedicated washer and dryer, and private French-door entranceideal for multigenerational living, extended guests, or a private retreat. Recent improvements provide peace of mind and make this home truly move-

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

Escape to country living while staying conveniently close to everything you need! Situated on a little over an acre and backing to approximately 118 acres of farmland, this property offers a rare combination of privacy, space, and potential. The main home features comfortable one-level living with three bedrooms, one-and-a-half baths, a charming country kitchen, hardwood floors, and a spacious family room with a cozy fireplace. The oversized detached ADU offers even more possibilities, featuring 2 bedrooms and 1 full bath, its own separate meter, and secure storage. Perfect for extended family, guests, a home office, rental potential, or a private retreat. With plenty of room to grow and make it your own, this property provides the space and flexibility you've been looking forall while enjoying the peaceful setting of open farmland directly behind you. Bring your vision and make this country property your own!

Welcome home to the Hampton model, featuring fresh paint, newer flooring, and updated carpet throughout! The main level showcases a welcoming two-story foyer and a soaring two-story family room flooded with natural light, along with dedicated formal living and dining room, a private study, and a chef-inspired grand kitchen with an expansive center island. Main level bedroom with a full bath for those not wanting steps. Upstairs, youll find four spacious bedrooms, two full baths, and a convenient upper-level laundry room. The fully finished lower level offers a fifth bedroom and additional full bathproviding plenty of flexible space for recreation, a home gym, or guests, plus abundant extra storage. All of this sits on a premium lot backing to open green space, offering a wonderful sense of privacy and serene views. Experience everything Leonards Grant community has to offer! Take advantage of neighborhood amenities like the community pool, basketball and tennis courts, rec center, and

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

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

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

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

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. Leonardtowns 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 t

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

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 prope

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, upgrad

Must-See Turn-Key Home on a Private 1-Acre Lot Backing to Trees! Welcome home to this beautifully maintained, turn-key 4-bedroom, 2-bathroom home offering approximately 2,100 square feet of comfortable living space. Situated on a private 1-acre lot backing to mature trees, this home offers plenty of space both inside and out. The inviting interior features a spacious and functional layout with plenty of room for everyday living and entertaining. The kitchen is equipped with stainless steel appliances and offers ample workspace for preparing meals. The adjacent dining room features a sliding glass door leading directly to the spacious deck, creating an ideal flow for indoor-outdoor entertaining. Four comfortable bedrooms provide flexibility for family, guests, a home office, or hobby space. The fourth bedroom is a special bonus, featuring its own sliding glass door providing direct access to the backyardperfect for a guest suite. Step outside and enjoy the peaceful, tree-lined setting f

IMMACULATE & Impressively Upgrades 4 Bed 3.5 Bath End-Unit Townhome w/ a 2. Car Garage & a Screened in Porch in Clark's Rest! Located in the highly sought-after Clark's Rest community in the heart of Leonardtown, this beautifully maintained end-unit townhome offers the perfect blend of space, comfort, and convenience. Just minutes from historic downtown Leonardtown, Leonardtown Wharf, restaurants, boutique shopping, parks, award-winning schools, and an easy commute to NAS Patuxent River, this home combines modern living with an unbeatable location. Featuring three spacious bedrooms, two and a half bathrooms on the upper level, and a versatile lower level currently configured as a fourth bedroom with its own full bathroom, this home offers exceptional flexibility for guests, a home office, fitness room, or additional living space. The open-concept main level is filled with natural light thanks to the desirable end-unit location. The gourmet kitchen showcases quartz countertops, abundant

Located in the sought-after Clark's Rest community, this home features Marricks 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, butlers pantry, and walk-in pantry, and opens to the family room with gas fireplace. Upstairs, the owners 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 Ame

Completely renovated and move-in ready! This beautifully updated rambler offers stylish one-level living with brand-new luxury vinyl plank flooring throughout, creating a seamless and modern feel. The stunning new kitchen features upgraded countertops, stainless steel appliances, and fresh finishes that make it as functional as it is beautiful. Both bathrooms have been completely renovated with today's buyer in mind, while new lighting throughout the home adds a bright, inviting atmosphere. A brand-new HVAC system provides added comfort and energy efficiency for years to come. Situated on over three-quarters of an acre and surrounded by picturesque farm fields, you'll enjoy peaceful country views and exceptional privacy without sacrificing convenience. Two brand-new decks provide the perfect spaces for entertaining, relaxing, or simply taking in the tranquil setting. If you're looking for a home where all the work has already been done, this beautifully renovated rambler is ready to we

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!

Welcome to Breton Oaksone of Leonardtowns most sought-after communitieswhere this beautifully designed to-be-built home by Mednick Construction offers the perfect blend of modern farmhouse style and peaceful, wooded surroundings. Tucked away on a private, wooded lot on a quiet cul-de-sac, this thoughtfully crafted residence delivers timeless curb appeal paired with todays most desirable open-concept living. Inside, youll find approximately 2,800 square feet of well-designed living space featuring 4 spacious bedrooms and 3.5 baths. The main level showcases 9-foot ceilings, and main level primary suite featuring a beautifully tiled shower and ample closet space. A cozy gas fireplace with hearth anchors the living space, while recessed lighting adds a warm, modern touch. Upstairs, enjoy the flexibility of a rec space and dedicated media roomideal for movie nights, a playroom, or a private retreat. An optional bonus room with a full bath over the garage provides even more opportunity to pe

Welcome to your new home! Situated on over an acre of cleared, open land. This charming one-level home offers amazing sunrise/sunset views and plenty of space to enjoy and entertain. Step inside to an open floor plan filled with natural light. Featuring 3 spacious bedrooms and two full baths. The living room has a cozy fireplace, creating the perfect gathering space. The kitchen overlooks the backyard and flows seamlessly into the laundry area and enclosed porch with a relaxing swing. Perfect for your morning coffee or unwinding in the evening. The large backyard features a fire pit, ample room for entertaining, gardening and recreation. Conveniently located within minutes of several local shops and within 45 minutes of Washington, D. C. Don't miss the opportunity to make this beautiful home yours! Professional photos coming soon

This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane in Avenmar; a water oriented community on Breton Bay. Its elegant facade overlooks the lovely landscaped yard. From the gourmet kitchen, wander on to the custom covered rear screened porch (almost 600 sq. Ft) where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled with natural light and overlooks the lush woodland and peaceful yard. The main level welcomes you with gleaming hardwood floors that stretch throughout. Formal living and dining areas are perfect for entertaining plus a dedicated office for quiet work-time. The family room off of the kitchen features a cozy wood burning fireplace as the centerpiece while the gourmet kitchen impresses with its high-end appliances, quartz counters and spacious pantry. The walk-out basement offers a fantastic space for movie night, family fun and projects while ample storage keeps everything organized and out of s