St. Michaels

History meets picturesque living in this delightful community

Welcome to St. Michaels

Tucked away on the Miles River, you’ll find one of Maryland’s best-kept secrets. Escape from it all in this historical, picturesque village that looks like it is the backdrop of a romantic movie. St. Michaels delivers all of this charm alongside fantastic dining, fun events, great schools, and a feeling of being away from everything that weighs you down.


With a population of just over 1,100, St. Michaels is small in size. However, don’t let that number trick you. It is home to impressive shopping and dining establishments and numerous things to do and see. Since the town is located on the water, it is also great for those who enjoy getting out on their boat or yacht.


Homes in St. Michaels also preserve the historic look and charm of the area. Nearly all of the surrounding neighborhoods are set just off of the main road (S Talbot St) and are suburban.  Median home values in this area are right around $525,500.


What to Love

  • Picturesque village tucked away from it all
  • Situated on the Miles River
  • Small town with plenty to do and see minutes from home

People & Lifestyle

St. Michaels is known for being incredibly peaceful and relaxed. It feels like a genuine escape from busy city life. When comparing it to the major U.S. cities that are within a two-hour drive, it is a 180 degree flip in terms of business and population. Life here is serene, happy, and taken at a slower pace.


What is fantastic about this area is that it is versatile enough to meet the needs of almost anyone. Families enjoy spacious homes and nearby schools. Those who live in the city routinely make St. Michaels their home away from home. Essentially, if you desire life at a calm pace in a community-centric locale, this town is a must to consider.


Dining, Shopping & Entertainment

Locally owned shops and delicious dining await in St. Michaels. As a resident, you’ll have no trouble finding your new favorite hangouts. 

Walk along S Talbot Street, and you’ll uncover wonderful local shopping. Plan stops at The Preppy Redneck, Woodcraft Artisans, Candleberry Shoppe, Chesapeake Bay Outfitters, and Guilford Company jewelry store. For those planning to welcome guests, there are multiple bed & breakfasts, as well as the stunning St. Michaels Harbour Inn, Marina & Spa.


You don’t have to leave town to have an amazing day or evening out. To start, check out St. Michaels Winery — a local producer of 18 exceptional wines. When you are ready to eat, dine at local favorites such as The Crab Claw, Gina’s Cafe, Limoncello Restaurant and Wine Bar, and Carpenter Street Saloon.


Things to Do

You also don’t have to go far to find fun things to do when you live in St. Michaels. Seasonally and year-round, there is a full line-up of activities and festivities.


Fans of locally caught oysters should mark their calendars for the annually held OysterFest. Watermen’s Appreciation Day is another local favorite. Rain or shine, this event is held at the Chesapeake Bay Maritime Museum and serves up tasty steamed crabs, beverages, family activities, and a boat docking contest.


Around town, be sure to explore other notable spots, including Muskrat Park, St. Michaels Museum, the St. Michaels Public Boat Ramp, the 1879 Hooper Strait Lighthouse, and Waterfront Park.



St. Michaels is home to several excellent schools. Top educational opportunities include:

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The Waterfront Group was a natural decision to form. This blended the waterfront lifestyle that Patrick lives to the marketing knowledge and experience he has gained in the industry. The Waterfront Group now serves those looking to buy or sell waterfront across the region with a trusted advisor and marketing expert.