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$4,995,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$1,995,000
4 Beds ⋅ 4 Baths
Waterfront living in Queenstown with sought-after southeastern exposure and 7 ft MLW, offering ideal conditions for boating and enjoying life on the water. Set on a beautifully landscaped, high-elevation lot, the property provides both privacy and peace of mind, with mature plantings, manicured grounds, and a paved driveway that creates a welcoming approach. This 4-bedroom, 3.5-bath home spans approximately 3,400± sq ft and is thoughtfully designed with a spacious, functional layout, including a first-floor bedroom and multiple living areas that capture natural light and water views throughout. The home features a bright sunroom overlooking the water, a partially finished basement for added flexibility, and a second-floor primary suite with a private balcony—perfect for taking in peaceful morning views. Outdoor living is equally impressive, with multiple areas designed for entertaining and relaxation. An expansive brick hardscaped patio anchors the backyard, offering seamless indoor-outdoor flow and the perfect setting for gatherings, dining, or quiet evenings by the water. The private dock, complete with a 12,000 lb boat lift, provides easy access for boating, with a quick run to the restaurants at Kent Narrows and the historic charm of St. Michaels. Additional highlights include a two-car garage and well-proportioned living spaces that offer both comfort and versatility. Conveniently located just minutes from Route 50 and the Bay Bridge, this property offers an ideal balance of waterfront lifestyle and accessibility. A strong waterfront offering in a desirable Queenstown location, combining elevation, views, and effortless boating access.

377 Hemsley Dr, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665