5 Landmark Estates from Eastern Shore Waterfront to Virginia Grandeur

Set on 7+ acres along Cooper Point Road in Bozman, this five-bedroom, five-full-bath, two-half-bath residence is organized for both togetherness and privacy, with distinct owner and guest wings. At the center, a gourmet kitchen anchors daily life, while a geothermal system supports year-round comfort with a lighter footprint. Outdoors, the experience turns decidedly resort-like: a gunite pool pairs with a heated spa for long afternoons that stretch into evening. Nearby, a dedicated pool house adds an outdoor kitchen, keeping meals and entertaining close to the water and sun. For boating and waterfront days, a private pier with lift and two slips is complemented by 7’+ MLW, making departures and returns feel effortless. Life here moves between winged interiors and an amenity-rich shoreline rhythm.

Size: 7.00+ acres

Set on a rare expanse just west of Clear Spring, Maryland, this 661-acre farm offers the kind of scale that’s increasingly hard to find intact. After being allowed to remain fallow for several years, the land presents compelling potential for a future organic farm or vineyard, with room to shape a vision that feels both purposeful and enduring. For those drawn to the outdoors, the property is equally suited to becoming a high-end hunting venue—an immersive setting where open acreage and water features define the experience. A creek winds through the landscape, complemented by two ponds that add quiet, reflective moments across the grounds. An artesian well rounds out the essentials, supporting the sense of self-sufficiency that comes with true acreage. Life here would unfold at an unhurried, land-first pace.

Along the water’s edge on Irish Creek, this 22.14±-acre estate stretches across more than 1,000 feet of pristine, navigable waterfront, framed by sweeping southwest-facing views and unspoiled natural beauty. A stately Colonial residence balances timeless architecture with comfortable sophistication, with rich hardwood floors, extensive crown molding, custom built-ins, and four wood-burning fireplaces shaping warm gathering spaces throughout. The main level is arranged for both entertaining and everyday ease, from the formal dining room to expansive living and family rooms, plus a well-appointed kitchen with island and pantry. A main-level primary suite adds its own fireplace, walk-in closet, and spa-inspired bath. Outdoors, days unfold between the Gunite pool and outdoor spa, built-in fire pit, bocce court, pond, and a vaulted three-season porch for watching boats and sunsets. A pool house and guest apartment above the detached four-car side-entry garage make hosting feel effortless.

Set on over a lush acre in McLean’s prestigious Langley Oaks, this renovated estate pairs privacy with modern sophistication, shaped by more than $1 million in recent upgrades. A custom basketweave marble foyer sets a refined tone, echoed in a marble-clad sunroom, extensive millwork, and 10.25-inch wide-plank European oak flooring throughout. The updated kitchen centers daily life with dual marble islands, Sub-Zero and Wolf appliances, and a walk-in pantry, while a bright breakfast room overlooks the tree-lined backyard. Entertaining flows into a family room anchored by a Nero Marquina marble fireplace and an Amish-crafted oak butler’s bar with backlit quartzite. Upstairs, the primary suite adds heated floors, an essential-oil steam shower, and dual illuminated walk-in closets. Outside, a fire pit, outdoor television, and fully fenced yard create a quiet retreat close to the city.

Set on 76+ acres along Tilghman Island Road in Wittman, this fully renovated estate balances classic country living with resort-like amenities. The main residence offers 8 bedrooms and 5.5 baths, while a separate 2-bedroom, 1-bath guest house provides flexible space for extended stays. Outdoors, days can unfold between a gunite pool and covered pavilion, a tennis court, and a tranquil pond. Equestrian life is equally well considered, with a 4-stall barn topped by a recreation loft. For those drawn to the water, a private pier with two slips and approximately 2.5’ MLW invites easy departures and unhurried returns. Here, weekends feel expansive—and weekdays can, too.

Size: 76.00+ acres