Living in Leonardtown, MD | Housing, Restaurants, Attractions | Long & Foster

Living in Leonardtown, Maryland

Leonardtown, Maryland, is an historic small town with an exuberant art scene. It is close enough to major cities like Alexandria to function as a bedroom community, although it is also its own self-contained community with satellite campuses of both the College of Southern Maryland and St. Mary's Hospital. Founded in 1708 and originally called Seymour Town, it was later renamed for Governor Leonard. Scenically located on the waterfront of Breton Bay, Leonardtown now attracts tourists from the surrounding area, especially when the town hosts the National Oyster Shucking Contest on the third weekend of October every year.

town square leonardtown md

Things to Do in Leonardtown, Maryland

Those living in Leonardtown, Maryland, enjoy a compact downtown that bustles with shops, restaurants and bars. Much of the social interaction in Leonardtown centers on the verdant town square, one of the last remaining historic town squares in the state. Leonardtown was also designated an Arts and Entertainment District by the state of Maryland in 2013. It was the first community to receive this honor in southern Maryland. Check out the Leonardtown Arts Center, which hosts both shows and classes right off the square, for a hearty sample of the artsy vibe.

The downtown Leonardtown neighborhood is also home to a new park and trail system that runs for three miles along the waterfront. Stay fit and healthy while enjoying the great outdoors in this area, which also sports a kayak launch so you can get out on the water. The city has a ton of community events and a decent nightlife scene. Restaurants run the gamut from fresh seafood to ethnic, and there is a modern supermarket in town, as well as small family-run grocers.

leonardtown md wharf

Real Estate in Leonardtown

There are a variety of homes for sale in Leonardtown, MD including several century-old historic properties around the center of town and new country-club-style developments, complete with golf courses, just outside of town on Breton Bay. Leonardtown real estate is mostly composed of single-family dwellings, but there are also some townhouses and apartments in the historic downtown.


Getting There & Around


What Locals Love

Don't Miss It

  • Westside Memorial and Pine Valley provides residents with plenty of space to run, jump, and play tennis, volleyball, and baseball, and features a skate park.
  • To show their thanks to local volunteer firefighters, the city celebrates with a week-long festival known as Carnival Week, which features music, food, fireworks, and the crowning of Manchester’s Fire Queen.
  • For a night out on the town, head to the Town Center where you’ll find plenty of restaurants to suit your cravings, whether it’s Italian, Asian, or classic American.


Leonardtown Real Estate at a Glance

  • 47 Homes Sold*
  • 152 Avg. Days on Market*
  • $589,999 Median Price*

*over last 3 months

Find Your Home in Leonardtown

There Are 57 Properties Available in Leonardtown



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