410-822-1415 | Benson & Mangold Real Estate

Barb Watkins | 410-310-2021 | barb.c.watkins@gmail.com

Eastern Shore Homes Real Estate by Barbara Watkins


Create Memories in a Home that has Stood the Test of Time

Some of the most charming real estate offerings along Maryland’s Eastern Shore are the historical homes. These homes are full of character, and each comes with its own unique background. Steeped in tradition, local towns and communities have historical roots reaching back to colonial times.

Barbara Watkins has completed the National Trust for Historic Preservation course for marketing and selling historic homes, and can help you understand all the factors involved in this niche market.


The town of Easton, more than three centuries old, has a storied past, surviving fires and wars. Easton is the Talbot County seat, and as such has historically been a hub of activity and trade in the area.

Easton’s historic homes date back to the 1700s and tend to reside on larger lots. These homes are also impressively elegant compared to those in surrounding towns. The town features beautiful tree-lined streets, reminiscent of the Old South. Easton has a variety of dining and shopping options, along with top-notch healthcare facilities at the Memorial Hospital at Easton.

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historic-st-michaelsSt. Michaels

The colonial village of St. Michaels, located on the beautiful Miles River and St. Michaels Harbor, has an abundance of historic sites, churches, and museums. St. Michaels, known as “the town that fooled the British,” was historically more of a tourist town than a center of commerce, and maintains a resort feel, with fun, whimsical shops, restaurants and other attractions.

Historic homes in St. Michaels are primarily early American Colonials and date back to the 1700s. Homes are within walking distance of the harbor and San Domingo Creek.

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The town of Oxford dates back to 1663. Designated as a seaport by Maryland’s first governor, the town was one of two ports of entry in the province of Maryland; Annapolis was the other. A “waterman’s town,” Oxford thrived thanks to wealthy tobacco plantations, the emergence of the railroad, and a booming seafood industry.

Today, the town has a more leisurely, residential emphasis, with a number of weekend and second-home owners residing here. Oxford features various recreational attractions, including a yacht club, five-star dining, and a community center. Most homes are within a half block of the water and are set behind charming picket fences and large shade trees. Homes in this area date as far back as the late 1600s.

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Cambridge, settled in 1694, is one of the oldest waterfront towns in Maryland and serves as the county seat for Dorchester County. Cambridge was once known for its shipbuilding industry, producing large coastal vessels such as skipjacks and bug eyes, along with log canoes made mostly from pine and oak.

The town offers a variety of historical, educational, and cultural attractions, such as the Harriet Tubman Museum, the Dorchester Arts Center, and more. Outdoor enthusiasts will enjoy the Blackwater National Wildlife Refuge nearby, the Choptank River Fishing Pier, or a tour on the Skipjack Nathan. Sailwinds Park, a multi-million dollar development project, includes a hotel, marina, cultural and visitor center, public beach, and performance venue.

The historic homes along the beautiful brick- and tree-lined High Street were once owned by governors, statesmen, lawyers, and other notable figures.

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Dreaming of a home rich in character and history? Contact Barbara for listings today!



The data relating to real estate for sale on this web site comes in part from the BrightMLS. Real estate listings held by brokerage firms other than Benson & Mangold Real Estate are marked with the IDX logo and detailed information about them includes the name of the listing brokers.


All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Benson & Mangold Real Estate shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.