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$1,500,000
4 Beds ⋅ 3 Baths
Spectacular Waterfront Retreat on almost 7 Acres in Exclusive Bennett Point! Welcome to your private paradise on the shores of serene Greenwood Creek! This extraordinary waterfront estate offers almost 7 acres of pure tranquility and luxury, surrounded by water on two sides for a true feeling of seclusion and peace. Your deep-water private pier is a boater’s dream — complete with 3 boat lifts and 2 jet-ski lifts ($150k value just in lifts alone)— perfect for crabbing, fishing, or setting out for a sunset cruise. The home’s Royal Blue Terracotta roof and accents make a bold architectural statement, while the full wrap-around deck ensures you’ll never miss a moment of the breathtaking waterfront views. Step inside and be transported to a stunning waterfront chalet (2x6 construction), where soaring ceilings, skylights, and warm wood accents create a cozy yet grand, open atmosphere. The nearly 3,000 sq. ft. of living space includes a magnificent 35’ x 17’ great room anchored by a floor-to-ceiling stacked-stone fireplace with a wood stove—powerful enough to heat the entire home! The open-concept of the great room, dining and kitchen areas make entertaining a joy. Kitchen features custom cabinetry, granite countertops, a beverage fridge, island, and ample dining space—flowing seamlessly to the screened porch and wrap-around decking. This home also enjoys over 2 thousand ft of heating tubes under the floor for warm-radiant heating you won't find anywhere else! The main level offers 3 spacious bedrooms, 2 full baths, and convenient laundry and storage areas. Upstairs, the cozy loft-style family room with skylights overlooks the great room and leads to a luxurious 25’ x 23’ primary suite, complete with a spa-inspired bath featuring dual sinks, a whirlpool tub, separate shower, and skylights that fill the space with natural light. Every inch of this home was designed to celebrate waterfront living at its finest—a place where comfort meets adventure, and every day feels like a getaway. 🌅 Don’t wait—this rare Bennett Point gem won’t last long!

2006 Bennett Point Rd, Queenstown

Listing courtesy of RE/MAX Executive. Contact:

$4,695,000
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:

$4,400,000
6 Beds ⋅ 6 Baths
Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.

200 Wye Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: