About the Area

The Eastern Shore of Maryland lies predominantly on the east side of the Chesapeake Bay and consists of nine counties. Just under 8 percent of Marylanders live in the region. It’s a place known for farmland and waterfront homes, steamed crabs and sweet corn. On weekends during the warmer months, the populations grows exponentially as people from Washington, D.C., Baltimore, Annapolis and more make their way to the shore to spend a weekend in peace.

But a weekend on the Eastern Shore is hardly ever enough. Many decide after spending time in one of our waterside villages or small arts towns that they’d like to retire here or buy a second home. Vacationers see it’s a great place to raise a family and start looking for their first place.

The residents of Maryland’s Eastern Shore consider themselves lucky to be surrounded by such natural beauty: coves and creeks, fields and forests. It’s a haven away from city life and suburbs.

Each area of the Shore has its own personality. Click on the links above to learn more about the counties we work in: Talbot, Dorchester, Caroline, Kent and Queen Anne’s.

View Homes for Sale in Talbot County, Maryland

About Easton, Maryland
Located in Talbot County, Md., Easton is a small arts community, about 10 square miles in size. It’s home to the famous Avalon Theatre and the beautiful Tidewater Inn. The town hosts popular festivals like Waterfowl Festival (November), Festival of Trees (November and December) and the Plen Air art festival and competition (July).

Easton is known for fine dining and great local shopping. The real estate market in Easton offers a wide variety of homes for people of all tastes and means. The downtown area is known primarily for stately historic homes. There are plenty of subdivisions, like Easton Club, Easton Village and Cooke’s Hope, with new and recent construction single-family and town homes. Fine estate homes are found on Easton’s plentiful waterfront, mainly along Oxford and St. Michaels roads.

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About Oxford, Maryland
Located in Talbot County, Md., Oxford is a quiet small town on the Tred Avon River. It’s home to the Oxford-Bellevue Ferry, the famous Robert Morris Inn and the Scottish Highland Creamery, which serves the best ice cream on the East Coast. The town’s sleepy streets are lined with brick sidewalks. There’s a waterside community park, a small town grocery store and a few restaurants for good sea fare. The town itself is a narrow peninsula surrounded by water.

Oxford is known more for its marinas and its beautiful homes than for tourist attractions. Homes downtown vary in price, but they are mostly historic, colonial-style homes. The waterfront homes are particularly prized. There are also fine estate properties close to town along Oxford Road.

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About St. Michaels, Maryland
St. Michaels is a maritime village built around the famous St. Michaels harbor. It offers a very different lifestyle than that of neighboring Easton and Oxford. St. Michaels is a tourist destination, full of great shops and restaurants. On weekends and summer afternoons, the streets of downtown are full of locals and visitors, looking for the blue crabs and ice cream in town. A few popular destinations are the Chesapeake Bay Maritime Museum (pictured here), the Crab Claw Restaurant and The Inn at Perry Cabin. People come to town for Carpenter Street Cart Races (St. Patrick’s Day), WineFest (spring), the antique and classic boat festival (summer) and Christmas in St. Michaels.

Real estate in the area consists mostly of historic houses in town and waterfront estates just outside of St. Michaels proper. There are a few upscale developments, like Martingham and Perry Cabin, plus some more modest developments like Back Creek Landing.

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Tilghman Island, Maryland
Tilghman Island is best described as an “old fashioned waterman’s community.” It is located on the westernmost tip of the county, and it is a popular place to live for those involved in the seafood business. It’s also a popular destination for those interested in fishing trips and other water adventures. Many people choose to buy a second home in Tilghman because of the privacy and fantastic Chesapeake Bay views found on the island.

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Cambridge, Maryland
As the county seat, Cambridge is the most populated area of the county. Its downtown area is going through a revitalization phase, and many new subdivisions are being built on the outskirts of town. There is also a new resort in Cambridge: the Hyatt Regency Chesapeake Bay, including a golf club and community.

Travelers with everything from skipjacks to hydroplanes make it a point to stop in Cambridge, where, for the past 103 years, the city has hosted the Cambridge Classic, a boat race on the Choptank River. For the golfers in the family there are two 18 hole courses: River Marsh at the Hyatt resort and Clearview at Horn’s Point. Then we have the Cambridge-Dorchester airport, sited on 354 acres, with a 20-foot elevation.

In the historic district of Cambridge exists one of the largest collection of vintage Victorian homes of any community on the Delmarva Peninsula. This is a waterfront city with a busy harbor, lots of restaurants and interesting historic sites to visit. A growing artist district is making life that much more interesting.

Some popular destinations are the fishing bridge, Sailwinds Park, the Cambridge Yacht Club, and the Cambridge Municipal Yacht Basin. Try to time your visit to see the Power Boat Regatta, usually at the end of July.

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Denton, Maryland
Denton is a small town poised on a hill that overlooks the Choptank River. Since the town’s founding in 1781, the town’s Courthouse Green has been the site of eloquent balls, circuses, baseball games, military parades, hangings, jailbreaks, and fistfights. Errant fireworks celebrating the end of the Civil War nearly destroyed the downtown on July 4, 1865. Today the annual Caroline Summerfest is held on the streets surrounding the courthouse in August.

Outside of town, there’s the fantastic Martinak State Park and great golfing at Caroline Country Club.

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Kent Island, Maryland
Kent Island, full of restaurants and marinas, is a popular stop for visitors (It’s the first place you see when you get off the Bay Bridge!). Centreville is the county seat. One of the benefits of living in Queen Anne’s County is having the easiest access, on the Eastern Shore, to Annapolis, Baltimore and Washington, D.C.

View homes for sale in Stevensville, MD

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