The Best Places to Live & Explore…
For Every Lifestyle

Living a Boating Lifestyle in Leonardtown, Maryland

Leonardtown is located in a pastoral section of Maryland between the mouth of the Potomac River and Chesapeake Bay at the southern end of a large peninsula.  Its downtown, with courthouse, handsome square, distinguished old stores, and old wharf on an inlet of the Potomac, make it easy to imagine what this town must have looked like in the 19th and early 20th centuries. Although there is not a large marina here, it is easy to get onto the Potomac and from there explore the many bays in the area. This area has been slow to be developed because of its distance from any city and the bridges that had to be crossed to get here.  Growth is now happening at a rapid rate, but it appears the community is exerting some control over the loss of farmland that would be devastating to the charm of the area.

Leonardtown is the county seat of St. Mary’s County. Along with the Mennonites, the U.S. military has a large presence here; the Patuxent River Naval Air Base employs thousands of soldiers and civilians.

Where to Retire in Leonardtown and Home Prices

There are a number of very nice developments in and around Leonardtown that baby boomers would like. Areas near the water and town are particularly desirable. There is one condo project overlooking the bay that definitely would appeal to active adults. Real estate prices reflect the desirability of living here. Also thanks in part to the strong military presence here, median home value was $469,312 in mid-2022, according to Zillow.

What Is Special about Leonardtown

Pastoral countryside with many farms; water just about everywhere; proximity to great boating on the Potomac; many upscale housing opportunities; and a charming central downtown on the river.

What Is Not Special about Leonardtown

Leonardtown has become much more expensive. Traffic and overbuilding threatens unless controlled. It is also somewhat remote

Climate and Physical Environment

Leonardtown is on an inlet of the Potomac River near the southern end of a peninsula. There are many gently rolling hills. On the eastern side of the peninsula is Chesapeake Bay.

Restaurants & Cultural Scene

The College of Southern Maryland maintains a small day campus here. For more serious culture Washington DC is about an hour away.


Crime rate is lower than average.

Medical Facilities

St.Mary's Hospital; Calvert Memorial Hosp is 17 Miles; Prince Frederick


Ronald Reagan Washington National is 47 miles. Baltimore Washington International Airport, which has frequent flights and low cost carriers such as Southwest Airlines, is 60 miles away.

Valuable Links

Town of Leonardtown

Your Stories about Leonardtown, Maryland

Add Your Story

Discuss this review of Leonardtown in the Forum

If you have suggestions on how could improve these reviews, contact us.

Suggest a community that you think is a great place for this lifestyle.

Tell us Your Story about this lifestyle or city. Add a Video about it.

Find Your Dream Lifestyle


Rate This Town