5 Grand Waterfront Estates and Countryside Retreats in Maryland and Virginia

Along the Chesapeake Bay on Tilghman Island Road in Wittman, this 116+ acre property pairs historic charm with modern amenities, all framed by panoramic water views from nearly every room. The main residence features a gourmet kitchen and an expansive living room with brick flooring, creating an easy rhythm for both everyday living and larger gatherings. Eight bedrooms include a main-level guest room, offering flexibility for hosting without sacrificing privacy. Beyond the house, the estate unfolds as a true working-and-waterside compound: a 2-bedroom guest house, a 4-stall barn, and two equipment barns sit alongside a private pier. Leisure spaces are equally considered, with a waterside pool, pavilion, and tennis court for long afternoons that drift into evening by the Bay.

Set on 6.95 landscaped acres in Bozman, this residence is gracefully positioned overlooking Leadenham Creek, with panoramic views from most of the house. Inside, the layout balances scale with privacy through distinct owner and guest wings, while a gourmet kitchen anchors daily life and entertaining alike. A dedicated fitness room and a music/bonus room add flexibility for work, wellness, and unwinding at home. Outdoors, the waterside pool and heated spa create an easy rhythm from afternoon swims to late-evening soaks. The pool house includes a fully equipped kitchen, extending gatherings beyond the main interior, while a dock house and private pier with two slips support life on the water. With 7’+ MLW, days can begin with coffee and end with a quiet return to the creek.

Along the water’s edge between the charming locales of Easton and St. Michaels, this impeccably maintained colonial estate offers approximately 1,000 feet of waterfrontage and panoramic water views enhanced by a southwest exposure. A grand private entryway and sleek blacktop driveway set a composed arrival. Outdoors, a gunite pool with an attached spa is joined by an outdoor spa, built-in fire pit, serene pond, and a bocce ball court—inviting long afternoons that drift easily into evening. The expansive porch, finished with a vaulted ceiling, frames gatherings with effortless indoor/outdoor flow. Inside, fine finishes and fixtures—including crown moldings, shiplap, and wainscoting—carry into an elegant formal dining room and a main-level primary suite. A pool house with living room, full bath, and second-floor office/flex space, plus an apartment above the garage with kitchen, bedroom, and bath, extend the estate’s versatility.

Along the shoreline of Deep Creek Lake, 3135 Turkey Neck Road pairs lakefront living with a residence that has been completely reimagined and exquisitely curated with Restoration Hardware furnishings and finishes throughout. Expansive walls of glass frame unobstructed, year-round views of the water and surrounding mountains, pulling the landscape into nearly every room. The open main-level layout feels both striking and effortless, anchored by a gourmet kitchen and soaring vaulted ceilings. Four dramatic stone fireplaces add depth and warmth, while a screened porch extends the living space for year-round enjoyment. Each bedroom is designed as a private retreat with its own en suite bath, offering comfort and privacy without sacrificing flow. Here, architecture, craftsmanship, and natural beauty meet in a daily rhythm shaped by light, fire, and lake air.

Down a private winding drive and perched on high ground, this 121-acre farm in Monroe, Virginia is designed for quiet days and far-reaching vistas. Dating to circa 1830, the farmhouse has been completely rebuilt in 2025, preserving the historic character of the original structure while embracing the comfort and efficiency of modern living. Inside, approximately 3,600 square feet unfolds across 3 bedrooms and 3.5 baths, where traditional character is intentionally paired with modern amenities. A striking red metal roof gives the home a crisp silhouette, and front and side porches extend daily life outdoors—ideal for lingering mornings, long conversations, and taking in sweeping views across the surrounding countryside to the Blue Ridge Mountains. It’s a place where privacy feels natural and the landscape sets the rhythm.