Available Listings

$1,795,000 (USD)
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Saint Michaels Area Residential Home

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216 E Chew Ave Saint Michaels, MD 21663

4 Bed
4 Baths
3575 sqft
MLS# MDTA2012450
Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is move in readyIt is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2 car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the Conservatory. It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for a master suite. Two sets of French doors open to either the front lawn or side yard for entertaining. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the sunrises and sunsets.With the lowest price per square foot for a Luxury, Waterview, in town home, it is also a comparatively excellent value.
Listing Courtesy of BRIGHT IDX / Listed By: Christopher Clinton, Coldwell Banker Chesapeake Real Estate Company
$1,650,000 (USD)
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Chestertown Area Residential Home

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8796 Maryland Parkway Chestertown, MD 21620

9 Bed
7 Baths
4776 sqft
MLS# MDKE2006596
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Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields.Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings.For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use.A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025–2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away.After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.
Listing Courtesy of BRIGHT IDX / Listed By: Tracy Stone, Coldwell Banker Chesapeake Real Estate Company
$1,350,000 (USD)
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Cambridge Area Residential Home

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5419 Ragged Point Road Cambridge, MD 21613

4 Bed
5 Baths
4512 sqft
MLS# MDDO2011562
Welcome to 5419 Ragged Point Road — Closer than you think to D.C., Baltimore, and Ocean City, a striking contemporary waterfront estate set on 11.88 private acres with an incredible 1,500 feet of frontage along serene Brooks Creek. Designed for those who appreciate the best of Eastern Shore living, this 4-bedroom, 2 full/3 half bath custom home, built in 2007, offers exceptional craftsmanship and luxury throughout with all the designer furnishings included.The gourmet kitchen is a chef’s dream, featuring marble countertops and top-tier appliances, including Wolf, Bosch, and Sub-Zero. The elegant primary suite offers a spa-like retreat with a soaking tub and separate shower. Expansive living spaces open to multiple balconies and decks, each perfectly positioned to capture breathtaking water views.Outdoor amenities include a private pier with approximately 3 feet MLW (mean low water), complete with water, electric, and a 12,000 lb boat lift — ideal for boating and fishing enthusiasts. For hunters, a duck blind on the property and abundant wildlife make this a rare hunting paradise.Whether you are savoring the sunrise over the creek, entertaining guests, or exploring the surrounding natural beauty, this extraordinary property delivers a lifestyle of unmatched tranquility and recreation.
Listing Courtesy of BRIGHT IDX / Listed By: Gwen Eskridge, Coldwell Banker Chesapeake Real Estate Company
$1,249,000 (USD)
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Queenstown Area Residential Home

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500 Nesbit Road Queenstown, MD 21658

5 Bed
5 Baths
3666 sqft
MLS# MDQA2017418
Virtual Tour
This is the quintessential Eastern Shore Waterfront Estate to turn into your legacy property. Sitting on over 12 acres just minutes from the Bay Bridge, this substantial craftsman built in 1914 once served as the primary residence for one of the lead engineers for the Pentagon, Jefferson Memorial, and other DC marvels due to its balance of proximity to the city and quality of life. Lifestyle amenities have improved since then with nationally renowned Queenstown Harbor Golf Resort and the marinas/dining options in Kent Narrows all minutes away. Privacy is paramount here with a wooded and gated entry lane but without sacrificing access due to the exit on Route 50 still less than a mile away. The sweeping views here are unmatched with the protected lands of Eastern Neck Wildlife Refuge across the Chester from the residence also guaranteeing this peace and tranquility for years to come. The home itself is a historic masterpiece with hardwood floors, hand blown glass windows, and grand center hall staircase. The connection with the water is celebrated here with multiple sunrooms boasting big water views for those special moments. A rough cut timber 2 car garage and workshop provides old Eastern Shore charm. Wildlife here is abundant for the outdoorsman and nature lover due to it being one of the first large parcels after crossing through the hustle and bustle of Kent Island. Invest wisely while improving your quality of life with your own waterfront sanctuary to create those special memories for generations.
Listing Courtesy of BRIGHT IDX / Listed By: Michael "Murphy" O'Neill, Coldwell Banker Chesapeake Real Estate Company