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$649,900
4 Beds ⋅ 3 Baths
Welcome to 144 Wye Knot Road, where peaceful country living meets everyday convenience. Nestled on 3 private, level acres, this spacious cape cod offers the perfect blend of comfort, functionality, and open space, all within easy reach of Easton, Annapolis, the Bay Bridge, and major commuter routes. A tree-lined paved driveway welcomes you home, while the classic exterior, complete with a full front porch, dormer accents, and an attached side-load two-car garage, creates timeless curb appeal. Inside, you'll find over 2,200 square feet of thoughtfully designed living space featuring four bedrooms, two-and-a-half bathrooms, and an ideal floor plan for both everyday living and entertaining. Formal living and dining rooms flank the welcoming foyer, while the rear of the home opens to a dramatic family room with soaring cathedral ceilings, abundant natural light, rich wood flooring, and a cozy gas fireplace. The kitchen serves as the heart of the home, offering Corian countertops, stainless steel appliances, a center island, generous cabinetry, and an informal dining area overlooking the backyard. Step outside to the spacious deck, perfect for morning coffee, summer barbecues, or simply relaxing while taking in the peaceful surroundings. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite. The finished bonus room above the garage provides exceptional flexibility and is ideal for a recreation room, home office, fitness room, playroom, or 4th bedroom/2nd primary suite. Additional features include dual-zone HVAC (replaced within the last 10 years), a tankless gas water heater (replaced within the last 10 years) and an EV charger-ready garage. The true highlight of this property is the land. Level, usable acreage like this is increasingly difficult to find and provides endless opportunities for gardening, recreation, entertaining, future outdoor amenities, or simply enjoying the peace, privacy, and beauty of country living. If you've been searching for a home that offers room to breathe without sacrificing convenience, 144 Wye Knot Road is an exceptional opportunity to enjoy the best of Maryland's Eastern Shore lifestyle.

144 Wye Knot Rd, Queenstown

Listing courtesy of RE/MAX Leading Edge. Contact:

$625,000
4 Beds ⋅ 4 Baths
Govern Grason - This home is ready for you to move in. The house has been freshly painted inside and outside; you will appreciate the hardwood floor throughout. The home features 4 bedrooms 3.5 baths and additional space for home office and Walkin storage area that would be finished for more living space if needed. Partial basement, as well as a nice garage with new doors and openers. All located on 2.17 acres. This house is a must see!

109 Governors Way, Queenstown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$549,900
4 Beds ⋅ 3 Baths
Professional Photos coming soon. TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

161 Greenwood Creek Rd, Queenstown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$569,000
4 Beds ⋅ 3 Baths
Absolutely Charming Eastern Shore Home with Beautiful Farm Views! Experience the peaceful charm of Queenstown living in this beautifully updated home situated on a gorgeous .83 acre lot surrounded by the natural beauty of Maryland’s Eastern Shore. Enjoy the slower pace of life with open farmland views, plenty of outdoor space, and a setting that feels away from the congestion while still being convenient to nearby shopping, restaurants, waterfront areas, and commuter routes. The welcoming front porch is the perfect place to relax and take in the scenic farm views, while the screened porch overlooking the backyard provides another wonderful space to enjoy the outdoors. Inside, this home is full of warmth and character with luxury vinyl plank flooring throughout the main level and thoughtful updates throughout. The upgraded kitchen features white cabinetry, stainless steel appliances, and a convenient laundry room nearby. The inviting family room offers a cozy wood burning fireplace, creating a comfortable gathering space. A main level office with a beautiful French door entry offers flexibility and could also serve as an additional bedroom, guest space, or hobby room. Upstairs, you will find three spacious bedrooms with fresh carpeting, including the impressive primary suite featuring a large ensuite bathroom, walk-in shower, dual sink vanity, and generous closet space. The additional bathrooms have also been beautifully updated. With abundant parking, nearly an acre of land, peaceful surroundings, and views that capture the best of Eastern Shore living, this Queenstown charmer is truly a special place to call home.

223 Overlook Dr, Queenstown

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$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
$4,700,000
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: (410) 280-5600
$599,000
4 Beds ⋅ 3 Baths
Queenstown - This 4 bedrooms, 2.5 bath home is located between Route 50 and Route 301, so great access to either. Nice country setting with no HOA. Bright and open kitchen/family room with also formal living room and dining room. Spacious bedrooms and a bonus room over the garage. You will enjoy the wrap around porch and country living, but still close to everything.

107 Chestnut Ln, Queenstown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$2,250,000
6 Beds ⋅ 5 Baths
If you love the water, this extraordinary Wye River property is a dream setting. Situated on the point with more than 1,400 feet of waterfront, this property is fully equipped for waterfront living with two piers, a private beach, and a boat launch. The custom 6,400-square-foot home offers exceptional space and comfort, featuring a brick front, four-car garage, double porches, and walkout access. Inside, the kitchen is beautifully appointed with granite countertops, solid wood cabinetry, a gas cooktop, stainless steel appliances, and both a full-size refrigerator and freezer. Brazilian cherry floors and tile throughout the main living areas add warmth and timeless character. The main home includes four bedrooms, with a spacious first-floor primary suite for convenient main-level living. A bright sunroom, also perfect as a crab room, adds even more charm to the first floor. Upstairs, two expansive living areas showcase sweeping 180-degree water views. These flexible spaces are ideal for a game room, media room, lounge, or additional gathering areas. A standout feature of the property is the full private apartment with its own entrance through one of the two garages. Complete, with a full kitchen, two bedrooms, a full bath, separate laundry room, living room, and dining area, it is ideal for extended family, guests, or possible rental income. Outside, the property continues to impress with a waterfront fire pit, storage, water and electricity at the piers. There is also room for a pool on the right side of the property, subject to county confirmation. Offered for the first time, this exceptional waterfront retreat is ready for its next owner.

351 Wye Rd, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com