5 Distinctive Maryland and Virginia Estates, from Waterfront to Old Town

Set on 5.29 picturesque acres in Brookeville, 20801 New Hampshire Avenue offers the ease of true one-level living in a spacious ranch-style residence. The home includes four bedrooms and three full baths, arranged in a functional layout designed for everyday comfort and straightforward flow. Two fireplaces anchor warm, inviting gathering spaces, while large windows pull in abundant natural light and keep the surrounding landscape present in the day-to-day experience. Outside, a detached three-car garage adds welcome flexibility—ideal for vehicles, hobbies, equipment, or extra storage. The setting delivers privacy and a sense of country tranquility, yet remains connected, with convenient access to major commuter routes, shopping, dining, and Montgomery County amenities. Here, there’s room to spread out, entertain, or simply enjoy the quiet rhythm of nature.

Along the water’s edge in historic Crisfield, Maryland, this one-of-a-kind waterfront estate spans 82+ acres across three parcels and carries a storied legacy as the legendary “Home of the Terrapin King.” Built in 1925, the beautifully updated residence balances Chesapeake Bay history with an easy sense of modern livability, with extensive recent improvements that keep its timeless coastal character intact. Surrounded by water on three sides, nearly every room is oriented to the landscape, framing sweeping panoramic views of the Chesapeake Bay and tidal marshes, plus sunsets that change the mood of the home by the hour. With five bedrooms and two full bathrooms, the layout offers space to host and room to retreat, all set within a setting that feels both expansive and deeply connected to the shoreline.

On a quiet stretch of Princess Street in Old Town Alexandria, this end-unit townhome balances classic charm with thoughtfully updated comforts. Built in 1990, the traditional floor plan is elevated by custom built-ins, crown molding, recessed lighting, skylights, and high ceilings, while a double-sided wood-burning fireplace creates an inviting focal point. As an end unit, two extra windows and just one shared wall bring in more natural light and a welcome sense of privacy. The kitchen has been refreshed with new high-end stainless steel appliances, including a Miele refrigerator and Bosch dishwasher, and a Bosch stackable washer and dryer sits conveniently on the second floor. With a bathroom on every level and generous closet space, daily life feels easy. The top-floor suite’s skylight invites starry nights, with Braddock Road Metro, restaurants, and shopping a short walk away.

On a quiet lane in Wye Mills, this residence is described as meticulously maintained, with a private, peaceful setting that keeps daily life feeling unhurried. The standout is a gunite pool—an enduring, resort-like centerpiece that invites long afternoons outdoors and easy summer evenings close to home. With privacy emphasized in the listing, the overall atmosphere reads as calm and secluded, a place where you can settle in and enjoy the grounds without distraction. Whether your routine leans toward solo downtime or hosting a few friends for a swim, the combination of careful upkeep and an established pool creates a simple, satisfying rhythm. Here, the luxury is in the maintenance already done and the quiet that surrounds it, leaving more time to enjoy the setting as it is.

Surrounded by over five private acres in Myersville and the sought-after Middletown school district, this custom-built estate balances refined living with serious utility. For car enthusiasts and hobbyists, nearly 3,000 square feet of garage space spans six bays, including a detached garage with an unfinished upper level and an attached garage with additional unfinished space above and rough-in plumbing—ready for whatever comes next. Inside, an open floor plan and soaring ceilings bring in abundant natural light. The gourmet custom kitchen anchors daily life and entertaining, while the screened-in porch invites quiet moments with peaceful views of the property. A main-level owner’s suite feels thoughtfully private, with remote-controlled blackout blinds, two walk-in closets with built-ins, and a spa-inspired bath featuring heated floors, dual vanities, a soaking tub for two, and a custom walk-in shower. Geothermal heating and cooling supports year-round comfort as the home grows with you.