Maryland’s real estate market is a captivating mix of historic charm and waterfront luxury. From the cobblestone streets of Annapolis to the posh suburbs of Bethesda, the state offers a rich blend of colonial architecture and modern opulence. Its proximity to Washington, D.C. has transformed areas like Potomac into havens for high-profile residents seeking privacy and grandeur.
Whether it’s a Chesapeake Bay estate or a palatial mansion tucked into rolling horse country, Maryland proves that elegance comes with a hefty price tag. Here’s a look at the five most expensive houses currently on the market in the Old Line State.
5. St. Michaels, MD – $9,950,000
Near downtown St. Michaels, this 17,402 square foot estate is listed at $9,950,000 and spans 8.6 acres with 6 bedrooms and 11 bathrooms. Set on Harris Creek with over 400 feet of water frontage, the property includes a 12,000 square foot main residence, a guest cottage, and a party barn with space for multiple cars or a trailered boat.
Features include a waterside pool, pier with 4-foot MLW, putting green, elevator to four levels, wine room, theater, library, and multiple kitchens. The guest cottage and barn offer additional living and entertaining areas, all surrounded by landscaped grounds and water views.
Where is St. Michaels?
St. Michaels is a town on Maryland’s Eastern Shore, located along the Miles River. It has a background in shipbuilding and water-based commerce. The town features marinas, seafood restaurants, and the Chesapeake Bay Maritime Museum. St. Michaels draws visitors with its walkable streets and waterfront access. It also hosts seasonal events and boating activities.
Foyer
Round table in the center holds a tall floral arrangement in a blue-and-white vase, surrounded by dark wood floors and a pale patterned rug. Twin staircases curve up both sides to a second-floor landing with white railings and wood handrails. Matching sofas with floral upholstery line the walls beneath framed artwork. Oval windows, side tables with lamps, and neutral wall tones finish the space.
Living Room
Sectional sofa wraps around a square wooden coffee table facing a white fireplace with a mounted television. Window seats with red patterned cushions sit beneath wide windows, and two armchairs are placed to the side. Curtains and valances match in design and frame the view of the water. Walls are painted in a soft tone, and dark flooring grounds the room.
Kitchen
Coffered ceiling in white and blue spans across a large kitchen and dining area. Central island with dark wood cabinetry contrasts with white perimeter cabinets and granite countertops. Dining table and chairs are placed near a fireplace with blue pottery on the mantel. Large windows and sliding glass doors line the back wall facing the water.
Bedroom
Four-poster bed with gold detailing stands against a neutral wall, paired with nightstands and framed artwork. Upholstered chairs with striped fabric face the fireplace near a patterned rug. Armoire and small bench are positioned along the far wall beneath full-length curtains. Layout remains symmetrical, with seating and décor distributed evenly throughout.
Bathroom
Walls are covered in light-patterned wallpaper, and the floor is tiled in white marble. Built-in soaking tub is framed by a raised platform and surrounded by decorative plates and framed art. Vanity with curved cabinetry holds a round mirror, and a cushioned loveseat with pillows sits across from it. Window treatments and soft lighting add to the overall layout.
Source: Robert Hryniewicki and Thomas A Keane @ Washington Fine Properties, LLC. via Coldwell Banker Realty
4. Stevensville, MD – $14,950,000
Set on 18 acres along the Chesapeake Bay, this 20,013 square foot estate is listed at $14,950,000 and features 8 bedrooms and 10 bathrooms, including 7 full and 3 half baths. The property includes a private pier with boat and jet ski lifts, a heated pool and spa with fountains, an outdoor kitchen, and a sandy beach.
The main residence offers a 2,500 square foot primary suite with a terrace, office, fireplace, and spa-style bath. Additional features include a theater room, gym, game room, wet bar, aquarium, two laundry rooms, elevator, and three fireplaces, with commercial-grade construction and panoramic bridge views.
Where is Stevensville?
Stevensville is a community on Kent Island in Queen Anne’s County, Maryland. It serves as a gateway to the Eastern Shore, located just across the Chesapeake Bay Bridge. The town includes residential neighborhoods, marinas, and local businesses. Stevensville has historic sites and access to waterfront parks and trails.
Living Room
Two purple sofas face each other across a black coffee table in the living room centered on a carved stone fireplace. Patterned drapes frame tall windows on three walls, and a painting hangs above the mantel. Colorful pillows and matching footstools add contrast to the neutral rug and wall panels. A coffered ceiling and chandelier complete the space.
Kitchen
Light cabinetry with dark countertops fills a large kitchen, where a long central island provides additional workspace and seating. Pendant lights hang over the island, and a red runner adds color along the tiled floor. Glass doors and large windows bring in views of the patio and water beyond. Multiple cooking stations, storage drawers, and built-in appliances are integrated throughout the layout.
Dining Room
Eight white chairs with metal ring pulls surround a dark wood dining table placed on a patterned area rug. A crystal chandelier hangs from the gold-toned ceiling, and arched openings connect the room to other parts of the house. Large windows line the perimeter, flanked by drapes in a bold circular pattern. Ornamental wood paneling and floral arrangements bring in added detail.
Bedroom
A bedroom opens up with vaulted ceilings and tall arched windows that lead to a balcony. A pair of oversized chairs and ottomans sit on a patterned rug in front of a fireplace, while a bed with a tufted headboard is set farther back. Ceiling fans and pendant lighting add functionality. The room is finished with light trim, wood floors, and full-length drapes.
Bathroom
There is a built-in soaking tub sits in the middle of a large bathroom surrounded by hexagonal tile flooring and floral wallpaper. Crystal strands hang from the ceiling as a decorative chandelier alternative. A long vanity with two sinks stretches along one wall, while French doors open to a balcony with water views. Orchids and soft lighting finish the space.
Source: Bradley R Kappel @ Ttr Sotheby’S International Realty via Coldwell Banker Realty
3. Fallston, MD – $15,000,000
Harford Hill spans 246.75 acres in Maryland’s countryside and features a 12,572 square foot Georgian-style main residence with 7 bedrooms and 10 bathrooms. Built in 1929, the property includes a 5,438 square foot party barn, two equestrian barns with a total of 19 stalls, a six-car garage, corn crib, tractor barn, newly remodeled barn, concrete block manger, and a 150×200 all-weather arena.
A pond anchors the landscape, which also includes the Pocock House and a specimen copper beech tree. The estate is under conservation and fox hunting easements and is listed for $15,000,000.
Where is Fallston?
Fallston is a suburban community in Harford County, Maryland. It is primarily residential with a mix of farms, neighborhoods, and small businesses. The area includes public schools, parks, and local shopping centers. Fallston is located near Bel Air and provides access to both rural and suburban lifestyles.
Foyer
A small hallway features arched doorways, framed artwork, and console tables with matching lamps. Wood flooring leads to a larger open space with a round table and a winding staircase. A coat rack holding umbrellas sits near the front door, which is topped with a glass transom. Trim details and neutral colors keep the space consistent with the rest of the home.
Living Room
Multiple armchairs, sofas, and coffee tables are arranged in a symmetrical layout in a spacious living room with white walls and a fireplace. Windows on three sides bring in daylight, and artwork is layered above sideboards and between window frames. Natural fiber rugs and light upholstery are used throughout. The fireplace features a white mantel with a deep surround.
Kitchen
A central island made of unfinished wood anchors the galley-style kitchen, surrounded by white cabinetry and open shelving. Industrial lighting fixtures hang from the ceiling, and large windows bring in natural light. Open shelving and glass-front cabinets line the walls above butcher-block counters. Stainless steel appliances, including a large range and hood, are integrated along one side.
Dining Room
Two long wooden dining tables with white chairs run parallel in a room with woven flooring and white paneled walls. A carved fireplace with wall sconces and a mounted sculpture creates a focal point, while modern artwork framed in purple hangs between multiple windows. Woven blinds and potted plants bring in natural texture. An additional high-backed seating area with a third table lines the wall.
Bedroom
In the bedroom, a four-poster bed with neutral bedding faces a fireplace. Windows on three walls let in views of the outdoors, and a woven rug covers the dark wood flooring. Two chairs and a small red table sit in the corner beside the fireplace. Trim and built-in wall panels match the room’s all-white palette.
Source: Heidi S Krauss @ Krauss Real Property Brokerage via Coldwell Banker Realty
2. Annapolis, MD – $19,995,000
Located in Annapolis and priced at $19,995,000, this 35,435 square feet estate sits on 23 acres and features 7 bedrooms and 13 bathrooms. Originally a Capuchin monastery, the main residence was restored in Georgian style and includes 18 fireplaces, a formal dining room, parlor, oversized ballroom, conservatory, gourmet kitchen, spa, wine cellar, and a secret vault.
The property includes a 3-bedroom, 2-bath guest/staff house, an Asian tea house, and mechanical facilities. It offers 1,500 feet of Severn River waterfrontage, a private 6-slip dock with 10’ MLW and boat lift, tennis court, 60-foot infinity pool, and a 9-car garage. Built with historic and modern elements, the home provides views, amenities, and proximity to downtown Annapolis and Washington D.C.
Where is Annapolis?
Annapolis is the capital of Maryland and sits on the Chesapeake Bay. It is home to the United States Naval Academy and has a strong maritime presence. The city’s downtown area features preserved 18th-century buildings and a working harbor. Annapolis also hosts government institutions and serves as a regional center for sailing and boating activities.
Kitchen
Black spindle-back stools line the outside of a large kitchen island with a speckled countertop. Cream cabinetry surrounds stainless steel appliances, including a built-in microwave and double oven. Two windows above the sink let in natural light, with scalloped valances matching those by the stove. A light wood plank ceiling and wide-plank floors add warmth to the space.
Dining Room
Tall arched windows line both sides of a long dining hall with vaulted ceilings and exposed dark wood beams. A large white fireplace serves as the central focal point, with a dining table set for twelve placed directly in front of it. Light yellow walls contrast with dark wood paneling and chevron-patterned wood floors. A grand piano sits off to the side near multiple armchairs and display tables.
Bedroom
A four-poster canopy bed with draped fabric and a pleated bed skirt anchors the bedroom. Light wood floors are mostly covered by a patterned rug, and large windows are framed by matching swags and curtains. The space includes a seating area and connects to another room with a fireplace and chandelier. Artwork and floral arrangements add detail to the otherwise subdued color scheme.
Bathroom
A built-in soaking tub sits beneath a wide window dressed with striped fabric valances and shutters. A rounded vanity with a large circular mirror and twin lamps occupies the corner across from the tub. A padded stool with a curved back is positioned in front of the vanity. Soft tones dominate the space, and the window offers a view of brick architecture outside.
Indoor Pool
Arched columns divide a long indoor pool area, where light walls and floors contrast with a pale blue ceiling. Wall sconces and sculptures decorate the space, including a wicker lounge chair placed on a patterned rug near the pool’s edge. Water features arc into the pool from the right-hand wall. Several statues are placed at intervals along the perimeter.
Source: Bradley R Kappel @ Ttr Sotheby’S International Realty via Coldwell Banker Realty
1. Oxford, MD – $19,995,000
Between Easton and Oxford, this 11-acre waterfront estate includes a 24,767 square foot home with 6 bedrooms and 12 bathrooms. Set across two parcels—one developed, one vacant—the main residence features a 2,300+ square foot primary suite, 7 gas fireplaces, indoor pool, spa, sauna, wine cellar, and second kitchen. Outdoor amenities include terraces with built-in barbecue and a private dock with 3-foot MLW, 2 boat lifts, 4 jet ski lifts, and a floating pier.
Where is Oxford?
Oxford is a small town on Maryland’s Eastern Shore, located along the Tred Avon River. It is one of the oldest towns in the state and has a history tied to shipbuilding and watermen. The town operates a seasonal ferry that connects it to nearby Bellevue. Oxford is mainly residential with a few marinas, restaurants, and inns.
Foyer
Curved staircases with wrought iron railings rise from a marble-floored foyer with tall ceilings and crown molding. A round wood table with a floral arrangement stands in the center, while a console table and mirror rest against one wall. Double doors with a transom window mark the main entrance. Light walls and ample lighting keep the space bright and open.
Living Room
Dark wood paneling and a coffered ceiling set a formal tone in the living room, centered around a green stone fireplace with a white marble surround. Built-in shelving flanks the fireplace, and a round mirror sits above the mantel. A large arched window brings in natural light and offers a view of the grounds. Upholstered seating and a round coffee table sit on a light rug over marble floors.
Kitchen
Multiple glass-front cabinets and built-in appliances line the walls of a spacious kitchen. A large island with a wood countertop and seating for five stands at the center, while a breakfast table with six chairs is placed near glass doors leading outside. A ceiling fan and pendant light add function over the island and dining area. Cream cabinetry and tile floors keep the space uniform and neutral.
Bedroom
A pink tufted settee with a plaid skirt sits in the middle of a marble-floored bathroom with light pink walls and white trim. A large glass shower with dual rainfall heads is set to one side, and a freestanding tub sits near an arched alcove. Two wood vanities with mirrors provide storage and counter space. The space connects to a dressing area through a wide doorway.
Bathroom
Lake views can be seen through the double doors of a bedroom painted in soft blue, with a tray ceiling and fireplace featuring a red marble surround. A four-poster bed is placed on a patterned rug over hardwood floors. Tall windows and French doors bring in light and open to a balcony. An arched doorway leads into the adjoining bathroom.
