Maryland’s rich history lives on through its oldest standing homes, each a remarkable survivor of time. From colonial farmhouses to elegant Georgian manors, these structures offer a glimpse into the lives of early settlers, revolutionaries, and prominent families who shaped the region. Built between the 1600s and early 1800s, many of these homes have been carefully preserved or restored, showcasing original craftsmanship and telling stories of endurance, conflict, and change. As you explore the 12 oldest standing homes in Maryland, you’ll step back into a world where every timber, stone, and brick has witnessed generations of history unfold.

1. Modern Farmhouse in Jarrettsville, Maryland (1700)

Built in 1700, Shoulderbone Farm is a timeless retreat nestled on 203 picturesque acres, seamlessly blending historic charm with modern luxury. This remarkable estate offers unparalleled privacy, making it ideal for horse and hound enthusiasts or anyone seeking a peaceful country getaway. The equestrian facilities are top tier, featuring a spacious bank barn with multiple stalls, a heated tack room, and space for farm equipment, while an automatic water system and integrated jumps cater to a variety of equestrian pursuits. The six-bedroom, five-and-a-half-bath residence elegantly combines period details with sophisticated updates, highlighted by a newly renovated primary suite, an upgraded kitchen, and an original 1700s dining room with a stunning fireplace. Panoramic views of rolling pastures create a tranquil ambiance, while a charming spring house offers a private space for reading or guests.

2. Georgian Home in Upper Marlboro, Maryland (1715)

Built in 1715, Bellefields is a distinguished estate set amidst 159.84 acres in the heart of Maryland’s horse country. This historic property blends peaceful seclusion with easy access to urban amenities, thanks to its proximity to Interstate 95. The stately main residence has been thoughtfully preserved and updated, offering nine bedrooms and seven bathrooms across 6,054 square feet of enduring charm and refined craftsmanship. Elegant rooms celebrate the estate’s rich heritage, while modern comforts ensure luxurious living. Outside, a nearly 4-acre pond and picturesque rolling terrain provide a serene backdrop for equestrian pursuits, recreation, or quiet retreat. Meticulously maintained stables and outbuildings complete the property, making Bellefields a true haven for both people and animals.

3. Colonial Revival Home in Accokeek, Maryland (1725)

Built in 1725, this distinguished home exemplifies Colonial Revival architecture, a style known for its harmonious blend of historical inspiration and early 20th-century updates. The brick exterior, symmetrical window placement, and prominent gabled dormers highlight the style’s homage to colonial-era design, while the expansive columned porch adds a gracious and welcoming touch characteristic of the Revival movement. Inside, the spacious layout features elegant details and modern amenities that complement the home’s classic aesthetic. Set on beautifully landscaped grounds, the property offers both timeless charm and comfortable living.

4. Georgian Home in Berlin, Maryland (1730)

Built in 1730, this remarkable property, proudly listed on the National Register of Historic Places, is a stunning example of Georgian architecture. Its iconic Flemish Bond brick checkerboard pattern reflects the craftsmanship of a bygone era, while original features like hand-carved raised panel wainscoting, intricate trimwork, and historic plank floors speak to its enduring character. The formal dining room showcases original woodwork and a unique corner cabinet from the historic Riddle Farm, while the stairway—enhanced with Federal Style details in the late 1700s—features a beautifully carved railing and newel post. Steeped in history, the Fassitt House withstood a cannonball strike during the War of 1812 and has remained in the same family for nearly 300 years. Carefully renovated in 1950 with a now-vintage kitchen, the home’s historic integrity has been preserved.

5. Colonial Home in Queenstown, Maryland (1740)

Built in 1740, this charming five-bedroom, four-bathroom home seamlessly blends historical elegance with modern comfort on a picturesque 31-acre estate. The main residence showcases classic colonial architectural details and spacious, inviting living areas, ideal for both relaxing and entertaining. Outside, a luxurious in-ground heated pool and hot tub create a private oasis for unwinding in style. Three additional outbuildings offer flexible space for hobbies, projects, or extra storage needs. Set amid serene natural beauty, this property offers the perfect mix of timeless charm and contemporary amenities.

6. Federal Home in Snow Hill, Maryland (1742)

Built in 1742, this magnificent Federal Era mansion, Chanceford Hall, beautifully blends timeless historic details with modern luxury across its six bedrooms and seven bathrooms. Located in the charming town of Snow Hill on Maryland’s Eastern Shore, the residence offers easy access to both tranquil beaches and vibrant metropolitan cities. Inside, soaring ceilings, ten fireplaces, grand Federal-style moldings, and expansive windows fill the home with elegance and light, while updates like a gourmet kitchen and modern HVAC systems provide contemporary comfort. Currently operating as both a private residence and a bed and breakfast, the property provides flexibility for future owners. Outside, enjoy beautifully landscaped gardens, a lap swimming pool, and spacious terraces for entertaining.

7. Georgian Home in Monkton, Maryland (1747)

Built in 1747, “Harmony Hall” is a beautifully renovated manor estate nestled along a long, tree-lined drive in the heart of My Lady’s Manor. This classic home is framed by stately shade trees and overlooks a heart-shaped, spring-fed pond and stream, offering a truly bucolic setting. Inside, the residence features stunning hickory flooring, high ceilings, deep window sills, and four fireplaces that add to its timeless charm. The estate also includes picturesque stone walls, a charming stone guest house, vibrant gardens, an eight-stall stable, and rolling meadows—all set on 33 secluded acres.

8. Gothic Revival Home in Hagerstown, Maryland (1750)

Built in 1750, the Elliott-Bester House is a captivating historic gem in the heart of the vibrant Arts & Entertainment District. This all-brick, Gothic Revival-style corner building offers 8,276 square feet of space—5,445 of which is finished—perfectly blending period charm with modern convenience for both residential and commercial use. The home’s historic character shines through original 18th-century doors, an elegant staircase, and intricate moldings, while updated amenities ensure comfort and flexibility. Ideally located just steps from exciting downtown attractions and the new Hagerstown Multi–Use Sports and Events Facility, the property features multiple offices, conference rooms, and restrooms to suit diverse professional needs.

9. Georgian Home in Leonardtown, Maryland (1755)

Built in 1755, this magnificent Georgian manor is the only one of its kind remaining in St. Mary’s County. The estate’s south façade overlooks a breathtaking mile-long “Avenue Field,” lined with trees and extending all the way to the Potomac River’s sandy banks. Inside, the manor retains exquisite 18th-century features, including a grand center hall and fully paneled great and dining rooms, with many original moldings, doors, and mantels still intact. Modern comforts such as air conditioning and heating have been added throughout. Two historic brick dependencies—The Kitchen and The Weaving House—flank the north entrance, forming a courtyard alongside gardens and orchards; the former has been remodeled into a guest cottage.

10. Federal Home in Annapolis, Maryland (1772)

Built in 1772 by Captain Beriah Maybury and known as the Kings’ Arms Tavern, this historically designated property demonstrates classic Federal architecture. This five-bay-wide brick home sits atop a high, scored stone foundation and features 9.5-foot ceilings illuminated by nearly floor-to-ceiling windows. The elegant library boasts built-in bookcases and a wood-burning fireplace, complemented by a two-room parlor, also with a fireplace. An addition, possibly from the 1830s, provides a spacious dining room with a high domed ceiling, a kitchen, and a cozy porch. Upstairs, four bedrooms—three with their own fireplaces—wood floors, two full baths, and laundry offer plenty of comfortable living space, while the partially finished basement with a separate entrance can be reimagined for various uses.

11. Georgian Home in Princess Anne, Maryland (1776)

Built in 1776, the historic “Beckford” mansion is a stunning example of Georgian and early Federal architecture in Princess Anne, Maryland. This stately home, set on nearly 8 acres of mature trees and open land, is recognized on the National Register of Historic Places. The mansion offers 5,445 square feet of living space, including a private guest suite, enclosed sleeping porch, two staircases, a private office, a walk-up attic, and an expansive unfinished multi-room basement. Inside, you’ll find eight fireplaces—one in a luxurious ensuite bath—impressive Federal-style woodwork, elegant plaster details, and grand doorways with a sweeping staircase. Modern comforts like 3-zone central air and an updated kitchen blend seamlessly with its historic charm, while the original smokehouse still stands behind the main home.

12. Colonial Vernacular Home in Frederick, Maryland (1778)

Built in 1778, this rare time-honored Colonial multi-family property stands as a two-unit jewel in Libertytown’s Village Center, offering endless possibilities. The main house features four bedrooms and one and a half baths, highlighted by beautiful wood floors, a screened-in back porch, and rich history dating back to the late 1700s. Attached is a separate two-story unit with two bedrooms and one bath, currently tenant occupied, making this an ideal opportunity for multi-generational living or rental income. The sale includes the main residence, two sheds, and a two-car garage with convenient off-street parking. A large, open backyard stretches all the way to South St., providing ample outdoor space to enjoy.