Maryland’s rich history is beautifully reflected in its century-old estates, where timeless architecture meets modern luxury. We journey through four magnificent homes that each whisper a story of elegance and legacy. From the refined 1924 Georgian Estate in Annapolis to the stately 1755 Georgian Manor in Leonardtown, the classic charm of an 1800 Traditional Home in Trappe, and the historic allure of an 1856 Colonial Estate in Knoxville, each property stands as a testament to Maryland’s enduring architectural excellence.
1. 1924 Georgian Estate in Annapolis
Built in 1924, this grand Georgian estate spans over 22 acres along the Severn River in Annapolis, Maryland. Known as “The Friary,” it underwent a significant renovation in 2008, blending classic architectural details with modern comforts. The 35,435-square-foot residence offers seven bedrooms, thirteen baths, and both formal and informal living spaces. Listed at $19,995,000, it features a nine-car garage, an infinity-edge pool, and 1,500 feet of prime waterfront.
Where is Annapolis?
Annapolis is the capital of Maryland, located on the western shore of the Chesapeake Bay near Washington, D.C. Founded in the mid-17th century, it is steeped in colonial history and home to the U.S. Naval Academy. Dubbed the “Sailing Capital of the U.S.,” Annapolis boasts a bustling waterfront, charming brick streets, and vibrant cultural events. Its proximity to major cities and rich maritime heritage make it a popular destination.
Riverfront Exterior
This aerial perspective highlights the estate’s expansive rear facade, complete with manicured gardens and a circular courtyard. The slate roof and classic brickwork reflect its Georgian design, while the infinity-edge pool seems to merge with the Severn River. Towering trees frame the property, offering privacy and natural beauty. A serene river view completes the picture of grand waterfront living.
Bedroom
A regal canopy bed draped in soft, flowing fabric anchors this expansive suite. Polished hardwood floors and refined crown molding enhance the room’s classic elegance. Sunlight pours in through large windows, illuminating artwork and plush seating. A nearby fireplace and seating area create a tranquil, luxurious retreat.
Indoor Pool
Arched openings and smooth limestone columns define this serene indoor pool area. A turquoise ceiling reflects softly on the water, while statues and accent lighting add a spa-like ambiance. A woven chaise lounge atop a patterned rug provides a comfortable spot to relax. Large arched windows let in natural light, emphasizing the pool’s classical design.
Kitchen
Bright and inviting, this kitchen features a large center island with a light-toned countertop and spindle-back barstools. Cream cabinetry and a matching range hood contrast with warm wood floors and ceiling paneling. Stainless steel appliances suit both everyday cooking and grand-scale entertaining. Recessed lighting and windows ensure a cheerful atmosphere for gathering and meal prep.
Music Room
A grand piano takes center stage on a richly patterned rug, reflecting the room’s refined character. A carved fireplace and tall windows lend classical charm and ample natural light. Stately columns and traditional artwork adorn the walls, enhancing the elegant mood. Plush seating invites guests to relax and enjoy music in a sophisticated setting.
Bathroom
Soft neutral tones and marble surfaces create a tranquil retreat in this spacious bathroom. A soaking tub sits beneath a broad window, offering a view of the home’s brick exterior and landscaped grounds. The circular vanity with an upholstered swivel chair adds a touch of elegance. Subtle lighting and polished fixtures complete the spa-like atmosphere.
Family Room
Warm wood paneling and arched windows shape a cozy gathering space in this family room. A herringbone-patterned fireplace anchors the room, flanked by comfortable armchairs and a trunk-style coffee table. Nautical artwork above the mantel nods to the home’s riverside locale. Sunlight floods in, highlighting the relaxed yet refined ambiance.
Source: TTR Sotheby’s International Realty via Zillow
2. 1755 Georgian Manor in Leonardtown
Built in 1755, this historic Georgian manor stands as the only remaining example of its kind in St. Mary’s County. Listed at $20,000,000, the estate spans 490 acres and includes 13,458 square feet of living space. It retains many original 18th-century features such as paneled walls and intact moldings while updates include heating and air conditioning. Recognized on the National Register of Historic Places, it offers panoramic views of the Potomac River and sandy shorelines.
Where is Leonardtown?
Leonardtown is situated in southern Maryland, close to the scenic Chesapeake Bay region. It lies roughly an hour and fifteen minutes from Washington, D.C., providing convenient access to major airports and attractions. The town is steeped in colonial history and known for its charming downtown, cultural festivals, and waterfront activities. Nearby points of interest include historic sites, local wineries, and the St. Mary’s County Regional Airport.
Grounds
An expansive lawn stretches from the manor’s grand brick façade to the surrounding farmland. Tall shade trees and manicured hedges frame the stately building, emphasizing its balanced, symmetrical design. A stone walkway leads to the main entrance, highlighting the formal landscaping and classic Georgian proportions. Soft, natural light enhances the serene atmosphere, offering a glimpse of the vast fields and distant horizon.
Bedroom
A canopy bed with intricately carved posts commands attention in this softly lit bedroom. Warm yellow walls and vintage floral textiles create a cozy, nostalgic ambience. Large windows overlook the lush grounds, bringing in abundant daylight and scenic views. Subtle cracks in the plaster and worn floorboards hint at the home’s rich 18th-century history.
Dining Room
Wood-paneled walls rise to a high ceiling, framing a stately fireplace at the center of the room. An elegant round dining table is surrounded by carved chairs, complemented by a richly patterned rug. Tall sash windows flood the space with natural light, illuminating antique clocks, artwork, and period furnishings. The warm glow of the fireplace and the refined woodwork reflect the manor’s gracious colonial heritage.
Parlor
A bold teal mantel surrounds the fireplace, contrasting with cream-colored walls and dark wood floors. An antique desk, brass fireplace tools, and a framed print create a tasteful historical vignette. Firelight flickers against the hearth, adding warmth and a gentle glow to the intimate setting. Traditional paneling and original hardware underscore the parlor’s 18th-century authenticity.
Kitchen
Exposed wooden beams accent the ceiling, while dark cabinetry provides a rich contrast to the neutral flooring. A modern stainless-steel refrigerator and range pair seamlessly with the rustic ambiance. Sunlight enters through a paned window above the sink, highlighting the blend of old and new. Generous counter space and updated appliances reflect plans for future expansion and renovation.
Source: Long & Foster Real Estate, Inc via Zillow
3. 1800 Traditional Home in Trappe
Originally built in 1800, this $8,800,000 estate spans nearly 48 acres along the Choptank River. Its white brick exterior, green metal roof, and eight fireplaces showcase its classic Traditional style. Recent updates include geothermal systems, while the 9,566-square-foot layout preserves historic charm.
Where is Trappe?
Trappe is a small town in Talbot County on Maryland’s Eastern Shore, near Easton and Cambridge.It offers scenic waterways, colonial heritage, and proximity to the Chesapeake Bay. Nearby attractions include historic Oxford, St. Michaels, and vibrant maritime museums.
Sunroom
Expansive windows line the walls, flooding the space with natural light and river views. A soft blue ceiling, wicker chairs, and potted plants lend a relaxed, breezy feel. Hexagonal floor tiles add texture, while a small table invites morning coffee or afternoon tea.
Bedroom
Sunny yellow walls and wide windows brighten this inviting space. A simple white mantel frames the fireplace, reflecting the home’s historic character. Polished wood floors and cheerful textiles create a warm, comfortable atmosphere.
Game Room
Exposed wooden beams and brick walls give this attic retreat a rustic vibe. A ping-pong and billiards table promise lively entertainment under soft overhead lights .Artwork and cozy seating areas make it ideal for friendly gatherings.
Breakfast Area
A built-in banquette with colorful cushions surrounds a wooden table under a woven pendant light. Floor-to-ceiling windows offer a peaceful view of the property’s grounds. Art, books, and collectibles enhance the relaxed, eclectic charm.
Foyer
A grand arched entry with decorative pilasters leads into the main hall. Muted green trim highlights artwork and complements the warm wood floors. A sweeping staircase forms the focal point, emphasizing the home’s spacious, traditional design.
Source: Benson & Mangold, LLC via Zillow
4. 1856 Colonial Estate in Knoxville
Crown Rose Estate, built in 1856, spans 75.69 acres in Knoxville, Maryland. Listed at $6,900,000, it showcases nearly 15 years of painstaking restoration and care. The 9,579-square-foot home features eight bedrooms, five baths, and seven fireplaces. Its historic character blends with modern updates, offering endless possibilities for events or agriculture.
Where is Knoxville?
Knoxville lies in Frederick County, Maryland, near the Potomac River and Appalachian foothills. It is conveniently located close to Harpers Ferry, with easy access to Washington, D.C., and Baltimore. Steeped in Civil War history, the area boasts scenic trails, wineries, and historical sites. Visitors can enjoy outdoor adventures, local culture, and the region’s rich heritage.
Porch
A spacious brick-floored porch framed by grand white columns greets guests at the main entrance. Wrought-iron chairs and tables overlook the circular driveway and manicured grounds. Potted plants and flowers add color, while mature trees offer shade on warm afternoons. The timeless design and tall pillars reflect the home’s classic Colonial elegance.
Ballroom
Soft gold walls embellished with hand-painted murals create an opulent atmosphere in this expansive room. Multiple round tables and elegant chairs invite formal dining or social gatherings. A stately fireplace serves as a focal point, complemented by tall windows that fill the space with natural light. Rich carpeting and refined details reflect the estate’s grand heritage and graceful ambiance.
Living Room
High ceilings and tall windows flood this lounge with soft, natural light. A fireplace and modern entertainment center balance historic charm with current comforts. Ornate chairs and plush seating form an inviting arrangement for conversation or relaxation. Neutral walls and subtle décor highlight the room’s spaciousness and timeless design.
Kitchen
Rich cherry cabinetry and polished granite countertops give this culinary space a warm, traditional feel. A central island with seating encourages casual dining and sociable meal preparation. An elegant chandelier and ample natural light showcase the room’s refined atmosphere. Modern appliances blend seamlessly with the estate’s overall historic aesthetic.
Bedroom
Floral wallpaper and a vintage canopy bed evoke a distinctly Victorian charm. A decorative fireplace, framed by ornate woodwork, adds warmth and character to the space. Wide windows usher in gentle daylight, illuminating the patterned rugs and furnishings. Soft lighting and tranquil colors create a cozy, romantic retreat for rest and relaxation.
Bathroom
Cheerful floral wallpaper and white wainscoting infuse this bathroom with a bright, classic look. A round accent rug and antique-style vanity underscore the estate’s timeless appeal. Wall sconces and a large mirror offer both practicality and understated elegance. Generous floor space and thoughtful detailing preserve the room’s historic charm.
Balcony
A covered second-floor porch overlooks the estate’s verdant lawns and stately trees. Wicker seating invites relaxation, making it an ideal spot for morning coffee or evening conversation. A softly painted ceiling and graceful columns nod to classic Southern porch design. Gentle breezes and scenic views complete this serene outdoor retreat.
