Leonardtown Homes with Colonial Style

Leonardtown Homes with Colonial Style

Welcome to Leonardtown, Maryland, a charming gem nestled in St. Mary’s County that beautifully combines rich history with modern conveniences. As the county seat, Leonardtown boasts a vibrant community atmosphere, where neighbors greet each other on tree-lined streets and local shops brim with character. This picturesque town is steeped in history, with roots dating back to the 17th century, offering a unique blend of heritage and contemporary living.

One of the most appealing aspects of Leonardtown is its stunning array of Colonial-style homes. These architectural masterpieces echo the town’s historical significance, featuring classic brick facades, symmetrical designs, and elegant details that transport you back in time. With their grand entrances and inviting porches, these homes exude charm and warmth, making them perfect for families and individuals seeking a sense of community and tradition.

Living in Leonardtown means enjoying a lifestyle enriched by nature and culture. The town is surrounded by picturesque landscapes, including the serene waters of the Chesapeake Bay and lush parks, perfect for outdoor enthusiasts. Additionally, Leonardtown hosts various events throughout the year, from farmers' markets to art festivals, fostering a close-knit community spirit.

Whether you’re looking for a cozy Colonial home with historical charm or a modern twist on classic architecture, Leonardtown offers an array of real estate options that cater to diverse tastes and preferences. Come explore this enchanting town and discover the perfect place to call home in Leonardtown, where history meets modern living in the heart of Maryland!

Newest Leonardtown Homes with Colonial Style

$550,000
4 Beds ⋅ 4 Baths
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!

41888 Jenkins Ct, Leonardtown

Listing courtesy of RE/MAX Realty Group. Contact:

$695,000
5 Beds ⋅ 4 Baths
Welcome Home! A covered front entry and separate covered sitting porch create a charming first impression. Step inside to a two-story foyer with hardwood flooring and elegant moldings that continue into the dining room. To the left, a versatile room is ideal for a home office, library, study, or playroom. The dining room flows through the butler's pantry and adjoining walk-in pantry before opening to the kitchen. A large center island anchors the kitchen, featuring granite countertops, abundant cabinetry, a gas cooktop, and double wall ovens. The kitchen opens to the family room, where a gas fireplace creates a warm and inviting gathering space. Upstairs, the owner's suite features a spacious bedroom, two walk-in closets with custom closet systems, and a private bath with a double vanity, a soaking tub with a tile surround, and a beautifully tiled walk-in shower with dual shower heads. Three additional bedrooms, a full hall bath, and a conveniently located upper-level laundry room complete the upper level. The finished walk-out lower level is designed for entertaining, featuring a spacious recreation room with easy access to the patio and backyard. A fifth bedroom with a walk-in closet, currently outfitted as a fitness room, is complemented by a full bath, offering excellent flexibility for guests, multigenerational living, or a private retreat. An unfinished storage room provides valuable additional storage. As the day winds down, the composite deck offers a peaceful place to relax and enjoy the changing colors of the evening sky. The fully fenced backyard features raised garden beds and generous open space for outdoor enjoyment. Located in the sought-after community of Clark’s Rest, residents enjoy an exceptional lifestyle with amenities that include a pool, clubhouse, playgrounds, tennis courts, sidewalks, jogging trails, and more. Just minutes from downtown Leonardtown, shopping, dining, and the Leonardtown Wharf, this home offers the perfect blend of comfort, convenience, and community. Seller is offering a one-year American Home Shield home warranty with an offer acceptable to the Seller. *** 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. *** Schedule your private tour today!

23214 Dairy Barn Dr, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$674,000
4 Beds ⋅ 4 Baths
Nestled in the serene community of Chestnut Hills of Leonardtown, this charming Colonial-style home offers a perfect blend of comfort and privacy. With 4 spacious bedrooms and 3.5 bathrooms, this residence spans an impressive 3,381 square feet, providing ample space for both relaxation and entertaining. Step inside to discover a warm and inviting interior. The open floor plan seamlessly connects the kitchen, dining area, and living spaces, making it ideal for gatherings. The kitchen is a chef's dream, complete with a butcher block island, modern appliances, generous cabinetry and plenty of counter space for meal prep. Crown moldings and chair rail add a touch of sophistication to the ambiance. The cozy family room, highlighted by a woodburning fireplace with glass doors and a mantel, creates a perfect spot for unwinding after a long winters day. The primary suite offers a very spacious private retreat with, large walk in closet and an en-suite bath, ensuring comfort and convenience. Venture outside to enjoy the expansive 2.89-acre lot, where nature surrounds you. The rear of the property boasts a beautiful retaining wall, a fire pit and backs up to Forest Retention Area providing a sense of continual privacy and tranquility. The outdoor space is perfect for entertaining or simply enjoying the peaceful views of the woods. Relax on the front porch, rear screened porch or deck, ideal for morning coffee or evening gatherings. The home also features a fully finished basement with both interior and outside entrances, offering additional living space, private gym area, private office, craft room or storage options. Create you own movie nights in the full theater room with projector and surround sound, which the equipment conveys. With an attached two-car garage and driveway, parking is a breeze. New roof and HVAC unit replaced in 2019. New water heater replaced in 2020. New insulated garage door 2026. Insulated crawl space and attic. French drainage system installed the home's perimeter. Additional features include a main floor laundry area and a security system for added peace of mind. As part of the Chestnut Hills community, residents have access to amenities, including rec field, basketball court, playground, and picnic areas, making it a wonderful place to call home. This property is not just a house; it’s a place where memories are made, and comfort is found. Experience the perfect blend of indoor and outdoor living in this delightful home.

20750 Deer Wood Park Dr, Leonardtown

Listing courtesy of Century 21 Redwood Realty. Contact: 5405331279
$615,000
5 Beds ⋅ 4 Baths
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 as this one won't last for long!

23620 Gunnell Dr, Leonardtown

Listing courtesy of Coldwell Banker Premier. Contact: 5406624500
$700,000
4 Beds ⋅ 4 Baths
Welcome to 21395 Fairwood Ct., an exceptional home offering over 3,500 square feet of finished living space on 0.85 acres in one of Leonardtown's most sought-after neighborhoods. Perfect for those looking to spread out and lay down roots. This spacious 4-bedroom, 3.5-bath home combines generous living areas, thoughtful updates, and a picturesque setting at the end of a quiet street near the cul-de-sac. From the moment you arrive, you'll appreciate the welcoming community—where neighbors gather for evening walks, children ride bikes, and the sense of home extends well beyond the property lines. Inside, the updated kitchen serves as the heart of the home, featuring a large center island with a built-in beverage refrigerator, beautiful finishes, and durable tile flooring that flows into the bright, bumped-out breakfast area overlooking the backyard. Multiple living and entertaining spaces provide the flexibility today's buyers are looking for, whether hosting family gatherings or enjoying everyday life. Step outside to your private backyard retreat. The fully fenced, level yard offers plenty of room for children, pets, gardening, or outdoor games, while the expansive deck and covered patio beneath a pergola create the perfect spaces for entertaining or relaxing. A large storage shed provides additional room for lawn equipment, tools, and seasonal storage. Upstairs, the oversized primary suite is a true retreat, complete with a spacious walk-in closet featuring laundry hookups for added convenience. Three additional generously sized bedrooms, each with ample closet space, complete the upper level. The finished basement expands the home's versatility with a spacious recreation area, full bathroom, and a bonus room—ideal for a home office, fitness room, playroom, hobby space, or guest accommodations. An unfinished storage area ensures you'll have room for everything. Completing the home is a generously sized side-load two-car garage. Offering the space to grow, the updates buyers appreciate, and a location that's consistently in demand, 21395 Fairwood Ct. delivers the ideal combination of comfort, functionality, and community. If you've been searching for a home that offers room to spread out without sacrificing convenience, this Leonardtown property is one you won't want to miss.

21395 Fairwood Ct, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$599,900
4 Beds ⋅ 4 Baths
Charming Home in Prime Leonardtown Location This inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops. Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining room connects through a butler’s pantry to a full walk-in pantry and flows into a modern kitchen featuring granite counters, upgraded cabinetry, stylish subway tile backsplash, large center island, gas cooktop, double wall ovens, and a premium Samsung Bespoke 4-drawer refrigerator with beverage center. The kitchen flows to an eat-in area and a cozy family room with gas fireplace flanked by beautiful custom built-ins. A powder room completes the main level. Luxury vinyl plank flooring runs throughout the main level and upstairs hallway, with hardwood stairs. Upstairs, the spacious primary suite includes a deluxe bathroom with dual sinks, soaking tub, ceramic-tiled shower, and a large walk-in closet. Three additional generous bedrooms, another full bath, and a sizable laundry room round out the upper level. The finished lower level offers a flex room, family room, full bath, and excellent storage. Outside, enjoy a composite deck, fully fenced yard, and firepit — perfect for relaxing or entertaining. Additional highlights include a 2-car garage and owned solar panels that keep utility bills impressively low. Enjoy resort-style living with neighborhood amenities including a spacious clubhouse, a 3,500 sq ft pool with separate kiddie pool, tennis and basketball courts, playground, and walking trails. Ideal location, thoughtful layout, and move-in ready condition — this home checks every box.

41444 Osborne Ln, Leonardtown

Listing courtesy of CENTURY 21 New Millennium. Contact: 3018622169
$485,000
4 Beds ⋅ 3 Baths
Buyers, come take a look. The estate just dropped the price by $20,000 This is an estate sale being sold AS-IS. The Estate will not make any repairs. The owner's bathroom shower has a leak and will probably need to be replaced. As you can see, it's listed well below market value. If you're looking for something to build equity, this could be the one for you. This Colonial features 4 bedrooms and 2 full baths and the laundry room on the upper level. The main level features an eat in kitchen, formal dining room, separate living room and a family room and a half bath/powder room. The unfinished basement features a 3-piece rough-in for another full bathroom. On the outside, there's a deck off the kitchen and the backyard has a vinyl privacy fence. Out front, there's a covered wrap around front porch and a side entrance too.

40659 Klear Ct, Leonardtown

Listing courtesy of Baldus Real Estate, Inc.. Contact:

$629,000
4 Beds ⋅ 3 Baths
CREDIT FOR REPAIRS!! New Lower Price!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Step inside to find gorgeous hardwood floors flowing seamlessly across the main level. The mostly finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, a spacious office area, a flexible bonus room, and a fascinating secret room hidden away for ultimate privacy or storage. Basement bathroom rough in ready for your unique finishes. Enjoy peace of mind with a brand-new tankless hot water heater installed at the end of 2025. Outside, the premium, fully fenced backyard boasts a 6-foot white vinyl privacy fence, offering a pristine and secure oasis for pets, play, or relaxing. Don't miss this one-of-a-kind home in a fantastic location! Situated in the highly sought after Leonards Grant neighborhood with tennis court, basketball court, community pool, large green, multiple playgrounds and recreation center. Within walking distance to Elementary School and very close to the amazing Leonardtown Square with restaurants, water views , and shops

23636 Hansel Ct, Leonardtown

Listing courtesy of Taylor Properties. Contact:

$645,000
4 Beds ⋅ 4 Baths
Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside. The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant cabinetry, a spacious walk-in pantry, and a convenient mudroom just off the rear-entry garage. Adding to the home’s incredible value are solar panels, allowing the current owners to enjoy no monthly electricity bill—an exceptional benefit that provides long-term energy savings. Step outside to your fully fenced backyard, where you’ll find an expansive paver patio designed for relaxing and entertaining. Gather around the built-in fire pit, host summer cookouts, or simply unwind in your own private outdoor retreat. Located in one of Leonardtown’s most desirable neighborhoods, Leonard’s Grant offers outstanding community amenities, including a pool, clubhouse, playgrounds, walking trails, tennis and basketball courts, all just minutes from downtown Leonardtown, restaurants, shopping, and not far from NAS Patuxent River. Move-in ready, energy-efficient, and perfectly located, this home offers the ideal combination of comfort

41462 Culpepper Way, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009
$649,000
5 Beds ⋅ 4 Baths
Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment. Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining room and kitchen. The spacious gourmet kitchen offers double ovens, ample cabinetry, and an eat-in area that opens to the comfortable great room with a gas fireplace. The main level also includes a powder room and a convenient laundry room that doubles as a mudroom just off the garage. Upstairs, the generous primary suite features a large bedroom, a private bath with a corner soaking tub and oversized shower, and plenty of space to relax. Three additional bedrooms complete the upper level. The finished basement provides additional living space, including a fifth bedroom, along with abundant unfinished storage space. With no carpet anywhere in the home, this property offers easy maintenance and a clean, updated feel.

23591 Margrave Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009
$579,900
4 Beds ⋅ 3 Baths
Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath colonial offers nearly 3,000 square feet of comfortable living space on a beautifully maintained 0.51-acre lot. Step inside to discover fresh updates, including new carpet and luxury vinyl plank flooring, creating a move-in ready home with a modern feel. The thoughtfully designed floor plan provides ample room for everyday living, entertaining, and working from home. The inviting family room features a cozy pellet stove, adding warmth and character during cooler months. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite with a private bath and plenty of closet space. The unfinished basement offers endless possibilities for future expansion, storage, a workshop, home gym, or recreation area. Adding to its potential, the basement is already equipped with a bathroom rough-in and a grinder pump cutout, making it easier to finish the space and add an additional bathroom in the future. Outside, enjoy privacy and peace of mind in the fully fenced backyard featuring a 6-foot privacy fence—perfect for pets, play, gardening, or outdoor gatherings. The attached two-car garage provides convenience and additional storage. Additional updates include a professionally installed radon mitigation system, offering added value and peace of mind. Ideally located just minutes from downtown Leonardtown, shopping, dining, schools, and commuter routes, this well-maintained home offers the perfect combination of space, comfort, and future potential. NOTE: Some photos have been virtually staged to show the home's possibilities. Don't miss your opportunity to make this beautiful property your next home!

23636 Gunnell Dr, Leonardtown

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$730,000
5 Beds ⋅ 4 Baths
Welcome to this exceptional home in the sought-after Leonard’s Grant community, where timeless design, quality finishes, and incredible indoor and outdoor living come together. From the inviting front porch to the private, tree-lined backyard, every space has been thoughtfully designed for comfortable living and effortless entertaining. Inside, stunning Tigerwood floors flow throughout much of the home, creating warmth and elegance. The main level features a private office, a spacious formal dining room, and a gourmet kitchen with abundant cabinetry, generous workspace, and a large walk-in pantry. The kitchen opens seamlessly to the bright, welcoming great room, while the spectacular sunroom is filled with natural light and overlooks the peaceful backyard. Step outside to the composite deck, which leads to a beautiful paver patio, offering multiple outdoor living spaces to relax, entertain, and enjoy the fenced backyard that backs to mature trees. Convenience continues with a main-level laundry room located just off the kitchen. Upstairs, the luxurious primary suite is a true retreat, complete with a spacious sitting area, an enormous walk-in closet, and a spa-inspired bath featuring a soaking tub and an oversized walk-in shower. Three additional bedrooms are located on the upper level, including a private guest suite with its own attached bathroom. The upper-level landing, accented by beautiful wood flooring, adds to the home’s open and elegant feel. The finished walk-out basement expands your living space with a large fifth bedroom, full bath, theater room, recreation room, and a wet bar—perfect for movie nights, entertaining, or hosting overnight guests. Walk directly out to the paver patio and enjoy the privacy of the backyard. Call for an appointment today!

23628 Belmar Dr, Leonardtown

Listing courtesy of RE/MAX One. Contact: 4437718009
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