St. Michaels, Md.

St. Michaels, the area’s most well known waterfront village, offers something different from Easton and Oxford. St. Michaels is a landmark; it’s “the town that fooled the British.” St. Michaels is bustling even on weekdays during the spring, summer and fall. There’s plenty of great shopping and tons of restaurants. A few popular destinations are the Chesapeake Bay Maritime Museum, the Crab Claw Restaurant and the famous Inn at Perry Cabin.

Real estate consists mostly of historic houses in town and waterfront estates just outside of St. Michaels proper. There are homes at every price point to accommodate almost any taste.

1,008

Est. population

78.9

Miles to Washington

208.9

Miles to New York

$372,500

Median home value

A town with history

What draws people — residents and visitors — to St. Michaels is its history. Many homes in the downtown area date back to the 1800s. These homes, and the red-brick sidewalks in front of them, transport you to another time. Even those who choose to live in newer homes have great access to museums, public parks and free street parking — all but disappearing in other parts of the world.

By land or by sea

Crossing Oak Creek isn’t the only way into town. Many people come to St. Michaels by boat and stay for a night or two at one of several marinas around the harbor. All shops and restaurants are within  minutes of the water’s edge. There are also several inns and bed-and-breakfasts for visitors who come by land.