Easton

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. Historic homes in Easton tend to be quite elegant compared to those in surrounding towns, and on larger lots. 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. Historic homes were built as far back as the 1700s, and range in price from $250,000 to $2 million.

St. Michaels

The colonial village of St. Michaels, located on the beautiful Miles River and St. Michaels Harbor, is rich with 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 within walking distance of the harbor and San Domingo Creek. Historic homes here date back to the 1700s and range in price from $400,000 to $1.5 million.
  

Oxford

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. Oxford features a number of recreational attractions, including a yacht club, 10 marinas, community tennis courts, a walking track, five-star dining and a community center offering plays, exercise classes, summer camps and more. Most homes are within 1/2 block of the water, and are set behind charming picket fences and large shade trees. Dating as far back as the late 1600s, these homes range in price from $400,000 to $1.5 million.
  

Cambridge

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 bugeyes, along with log canoes made mostly from pine and oak. The town offers a variety of historic, 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, will eventually include 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 onced by governors, statesmen, lawyers and other notable figures. Cambridge homes can range from $200,000 to $1 million.