5 Maryland Estates from Eastern Shore Waterfront to Bethesda Luxury

Set on 350 acres in Easton, Maryland, this estate unfolds as a complete compound, with distinct owner and guest wings and a 5-bedroom, 7 full-bath, 2 half-bath main residence. Inside, a gourmet kitchen anchors daily life, while soaring glass walls and heated limestone floors bring light and warmth through the seasons. An elevator adds ease across levels, and multiple decks extend living outdoors. Guests are equally well considered with a 4-bedroom, 2-bath guest house, plus a caretaker’s cottage. Leisure and land converge in an infinity pool and spa, a covered pavilion with kitchen, and a tennis/pickleball court. Working amenities include a 9-stall barn, alongside farmland, vineyards, and hunting grounds. On the water, piers with lift, two slips, and a floating dock offer 4′ MLW for easy days afloat.

Along the water’s edge on Tilghman Island Road in Wittman, this fully renovated estate unfolds across 115+ acres, with an additional 34-acre perc-tested waterfront lot included. An expansive waterside living room is framed by panoramic views, while the gourmet kitchen anchors day-to-day living and entertaining. Main-level guest quarters add flexibility, and a separate 2BR/1BA guest house extends the sense of retreat. Outside, an expansive waterside patio leads to a gunite pool with a covered pavilion, plus a tennis court for afternoons in motion. Equestrian and hobby pursuits are equally considered with a 4-stall barn and recreation loft, multiple fenced animal enclosures, and a pond. The pier offers two slips with 2.5′ MLW, setting an easy rhythm for time on the water.

Set on 7+ acres in Bozman, this five-bedroom, five-full-bath, two-half-bath residence is organized into distinct owner and guest wings that allow everyday life to unfold with ease and privacy. At the center, a gourmet kitchen anchors gatherings, while a geothermal system supports comfort with a lighter footprint. Outdoors, a gunite pool pairs with a heated spa for long afternoons that drift into evening. A dedicated pool house extends the season with an outdoor kitchen, creating a natural hub for relaxed entertaining. For time on the water, a pier with lift and two slips offers direct access, complemented by 7’+ MLW for confident boating. Days here move seamlessly from kitchen to pool to dock, following the rhythm of the land and shoreline.

Size: 7.00 acres

Beyond a private setting in Bethesda’s Longwood/Armat neighborhood, this one-of-a-kind residence pairs an award-winning vision by architect John Katinas of Katinas-Bruckwick with the craftsmanship of renowned homebuilder Paul Katinas. Perched on a private, approximately half-acre lot, the custom-built design unfolds across three levels, with extensive living space complemented by an additional 1,000 square feet of thoughtfully planned outdoor living areas. The approach is unmistakably contemporary in spirit, with every inch described as meticulously planned and executed, reflecting striking design and phenomenal attention to detail. Modern amenities are woven throughout, supporting both everyday ease and effortless entertaining. From morning routines to evenings spent moving between interior rooms and the outdoor living areas, the experience is defined by intentional design and a strong sense of privacy.

Along the water’s edge in Royal Oak, Anderby Hall unfolds as an Eastern Shore estate rooted in an original 1680 land grant. The 12± acre parcel traces 3,260’± of mostly rip-rapped shoreline, with a tidal pond, an island accessed by bridge, and a private peninsula and cove—nearly every vista oriented to Irish Creek. A gated driveway arrives at a 3,000± sq. ft. Colonial where a fireplace-warmed great room is detailed with charming old pine floors and hand-hewn ceiling beams. The granite kitchen centers on an island, while the primary suite offers his-and-her closets and a second-floor office/den area. Brick walkways lead to a waterside pool, and the dock with 5’ MLW sits minutes from the Choptank River. A 2,600 sq. ft. guest house, tennis courts with gazebo, multiple garages, and a workshop complete a setting alive with geese, ducks, deer, and turkey.