Maryland's Eastern Shore

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Waterfront Homes

Miles of shoreline along the Chesapeake Bay and its tributaries provide ample opportunities for waterfront living.  If you want a front-row seat to the water, let's talk about your goals, be it boating, water activities, or simply enjoying the view, there are many variables to Eastern Shore waterfront property.  I am here to help navigate those and help you make the best investment.

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Luxury Properties

What is your definition of luxury? For some it is high-quality fixtures and finishes; for others, it is acreage and privacy.  Here are some of the finest properties available on Maryland's Eastern Shore.

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Inland and Village Properties

Our downtown areas are dotted with charming bungalows and historic homes that offer an easy stroll into town for shopping, dining, and entertainment. There are also numerous neighborhoods, both old and new, to enjoy the Eastern Shore lifestyle.

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Explore all of our towns


Consistently recognized as one of America's best small towns and top 100 Arts Communities, Easton is a small town with ample amenities. With a jet airport, a vibrant arts and entertainment community, world-class restaurants, and a beautiful downtown chock full of interesting shops and historic buildings, you won’t soon tire of this little town. Residential living offers a little something for everyone -- majestic historic properties, waterfront estates, family-oriented neighborhoods, golf, and waterfront communities. 

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St. Michaels

Perhaps the most famous Talbot County town, St. Michaels, has a robust historic district and waterfront. Eclectic shops, crab houses, gourmet and inspired restaurants, and marinas all comingle with the Miles River in the background to create a perfect picture of how small-town living should feel. The town proper offers various historically important homes, cottages, or renovated properties, while the outskirts offer some of the East Coasts' most desirable estate properties. There are also family neighborhoods and golf and water access communities.

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Oxford is a charming small town with a slow and lazy speed limit of 25 mph and no traffic lights. Surrounded by water on three sides, the town enjoys a nautical ambiance from all venues. The town park offers expansive water views of sailboats passing by, and dining options are nearly all waterfront. The Strand, a public sandy beach, all afford residents the chance to interact with the water. Grand historic homes along S. Morris Street intersperse with charming cottages home to full-time and weekend residents. The many marinas offer first-class accommodations for boaters, and the Tred Avon Yacht Club hosts a very active sailing community.

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Located on the southern bank of the broad Choptank River, the seat of Dorchester County dates back to 1684, making it one of the oldest colonial cities in the state. When James Michener was researching his novel Chesapeake, he reportedly called Cambridge's High Street one of the most beautiful streets in America. He modeled his fictional city Patamoke after Cambridge. Many of the gracious homes on High Street date from the 1700s and 1800s. Locals love the variety of restaurants, new ones opening regularly, and eclectic shops in the downtown area. Horn Point Laboratory is home to the largest oyster hatchery on the East Coast.

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Kent Island and Queen Anne's County

The Kent Island area offers full-time residents and second homeowners easy access to and from the Western Shore with proximity to the Bay Bridge. There is a mix of residential communities, and waterfront condos appeal to families, vacationers, and boaters.  Further from the Rt. 50 corridor, you'll find sprawling waterfront estates and beautiful family communities.  The nature lover will find all they need with the six-mile Cross Island Trail. It offers a paved trail that meanders through the local creeks and marshes or Terrapin Beach Park, a 276-acre nature park featuring 3.25-mile oyster chaff walking trail along wetlands, tidal ponds, and sandy beaches. If it's seafood you are after, you'll find many waterfront restaurants specializing in local Maryland bounties.

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