Are you making a move to Southern Maryland? Discover Leonardtown with its blend of small-town charm, cultural richness, and proximity to gainful employment, making it an ideal destination for a dynamic and fulfilling lifestyle in St. Mary's County, Maryland.

Embrace a vibrant lifestyle in this historic gem founded in 1660. This is the county seat, where all County Government is conducted, and the Health Department is located. Uncover the town's rich history at Courthouse Square and the iconic St. Mary's County Courthouse. Home to the Saint Mary’s County Fair, a CSM Community College campus, a MedStar Hospital, and the highest rated K-12 schools in the area, you’ll experience the convenience and charm of small-town living with quaint shops, art galleries, and popular local restaurants. 

Enjoy leisurely strolls along the waterfront at Leonardtown Wharf, offering picturesque views of Breton Bay, where you can rent kayaks, or put your own in the water using the public launch. During the warm weather months you can take a sunrise yoga class right on the serene waterfront. On weekends during the summer months you can even get around town on the free trolley.

Beyond the charm, Leonardtown is within a short commute of work hubs, making it an ideal home base. Find the perfect work-life balance as you explore nearby opportunities while enjoying the town's community events that foster strong connections, such as Art Festivals, Holiday Celebrations, Performing Arts, and “First Fridays”, where all the business are open late and offer specials at their establishments; and many showcase local artists.

Visit the Port of Leonardtown Winery, where you can savor locally produced wines, and listen to live music.

Housing in Leonardtown ranges from apartment rentals, to affordable starter homes (many built in the 40s, and 50s), to established neighborhoods with mid-priced homes built in more recent decades, to new construction featuring single family homes and town homes in three new communities, to an array of waterfront properties, and even historical properties.

There’s something for everyone in this vibrant, inclusive community, so come out and see for yourself what Leonardtown has to offer! See MAP