The Guide to Living in Saint Michaels, Maryland

On Maryland’s Eastern Shore, a historic small town with a legendary past

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SAINT MICHAELS, MARYLAND

The History of Saint Michaels, Maryland

Located along the Miles River in western Talbot County, Maryland, the historic town of Saint Michaels, Maryland is among the Mid-Atlantic’s most iconic destinations and among the many gems of Maryland’s Eastern Shore.

Founded in 1778 as a speculative development for a Liverpool merchant firm, Saint Michaels, Maryland is named after an Anglican church established long before its creation.

Since its foundation, Saint Michaels, Maryland’s primary industry has been shipbuilding, with its primary export being a fast schooner style boat known as the Baltimore clipper. During the War of 1812, Saint Michaels, Maryland earned the reputation as “the town that fooled the British” for its clever strategy to evade incoming fire from the invading British forces.

As Saint Michaels, Maryland grew through the 19th century and into the 20th century, the local economy vacillated with the fortune of the surrounding agricultural enterprises and the Chesapeake Bay seafood industry, with oyster farming and crabbing evolving as the predominant local economy.

Today, Saint Michaels, Maryland is enjoying a renaissance with considerable restoration and rehabilitation of historic buildings in its central town square, and continues to serve as one of the most desirable destinations in the entire Mid-Atlantic region as a result of its enviable location along the Chesapeake Bay.

The Ship’s Point Estate of Easton, Maryland. Image courtesy of Anice Hoachlander.

THE ART OF LIVING

The Homes of Maryland’s Eastern Shore

Discover the most iconic homes of Maryland’s Eastern Shore, the Mid-Atlantic’s premier destination for waterfront living.

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Browse homes for sale on Maryland’s Eastern Shore presented by Sotheby’s International Realty.

SAINT MICHAELS, MARYLAND

“On Maryland’s Eastern Shore, historic charm and waterfront sophistication converge in the town of Saint Michaels, Maryland.”

— Byron V. Hughey

Janes Island, Maryland. Image courtesy of Mick Kirchman.

TRAVEL GUIDE

A Weekend on Maryland’s Eastern Shore

Featuring majestic waterfront vistas and a distinct sporting heritage, a weekend on Maryland’s Eastern Shore is the perfect escape from the hustle and bustle of city living.

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SAINT MICHAELS, MARYLAND

Frequently Asked Questions

Explore common questions about life in Saint Michaels, Maryland, including the best neighborhoods, restaurants, and more

DOES SAINT MICHAELS, MARYLAND HAVE A BEACH?

While Saint Michaels, Maryland is a waterfront town, it does not have a public beach.

WHEN IS THE BEST TIME TO VISIT SAINT MICHAELS, MARYLAND?

For those who seek to experience the very best of what Saint Michaels, Maryland has to offer, a visit during the Spring and Summer months would be an ideal time to take advantage of the gorgeous waterfront amenities and explore the shops and boutiques in the historic downtown. During the Fall, the Waterfowl Festival in nearby Easton, Maryland offers a fantastic opportunity to experience the unique sporting community of Maryland’s Eastern Shore.

WHERE IS SAINT MICHAELS, MARYLAND LOCATED?

Saint Michaels, Maryland is located in Talbot County on Maryland’s Eastern Shore on the south side of the Miles River.

WHAT IS THE PROPERTY TAX RATE FOR SAINT MICHAELS, MARYLAND?

Property taxes for Saint Michaels, Maryland are calculated per every $100 of assessed value and are broken out into three separate segments. For 2024, the county rate is $0.6165, the state rate is $0.1120, and the municipal rate is $0.470. In total, property taxes in Saint Michaels, Maryland come to a total of $1.1985 per $100 of assessed value.

IS SAINT MICHAELS, MARYLAND A GOOD PLACE TO LIVE?

For those who seek a quiet, small town environment with a distinct waterfront lifestyle, Saint Michaels, Maryland is a great choice. However, for those with regular commitments to the Washington Metropolitan Area, the reliance on the Chesapeake Bay Bridge as the primary means of access, many residents of Saint Michales, Maryland are vacation home owners and retirees.

HOW MUCH DOES IT COST TO BUY A HOME IN SAINT MICHAELS, MARYLAND?

The median sale price for a single family home in Saint Michaels, Maryland is $485,000, which is about 40% higher than the national average of $308,980. Ready to buy the home of your dreams? Browse homes for sale in Saint Michaels, Maryland presented by Sotheby’s International Realty.

WHAT IS THE SCHOOL DISTRICT FOR SAINT MICHAELS, MARYLAND?

Residents of Saint Michaels, Maryland would attend Talbot County Public Schools, including St. Michaels Elementary School and St. Michaels Middle High School.

WHAT IS SAINT MICHAELS, MARYLAND KNOWN FOR?

Aside from its historic downtown and unique waterfront location, Saint Michaels, Maryland is perhaps best known as the setting for the popular movie, Wedding Crashers. However, for history buffs, Saint Michaels, Maryland has been dubbed “The Town That Fooled The British” as a result of their clever means of avoiding British naval attacks during the Revolutionary War.

HOW FAR IS SAINT MICHAELS, MARYLAND FROM WASHINGTON, D.C.?

Saint Michaels, Maryland is roughly 80 miles from downtown Washington, D.C. The most common way to get to Saint Michaels, Maryland from Washington, D.C. is by car, which requires crossing the Chesapeake Bay Bridge.

WHAT ARE THE BEST RESTAURANTS IN SAINT MICHAELS, MARYLAND?

Saint Michaels, Maryland features several outstanding restaurants, including Ruse at The Wildset and Stars Restaurant at the famous Inn at Perry Cabin. For a more casual feel, Foxy’s Harbor Grille offers waterfront dining, great seafood, and a wide selection of cocktails, including Maryland’s famous Orange Crush. For a classic steakhouse experience, Theo’s Steaks, Sides & Spirits is a solid option. And for a cold beer and live music, you can’t beat the Carpenter Street Saloon.