Leonardtown : Maryland


What It Is Like to Retire in Leonardtown

Leonardtown is a very small town 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. 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. On the way into town one drives past the modest farms of an old order Mennonite community to the northwest, along with occasional horse and buggies. 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. 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. However development is on the way. A very large condominium project is now at the redeveloped wharf. Many upscale homes on big lots have been built in any area near the water, such as in Breton Bay. 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.

For a list of profiles of over 1000 cities and towns go to retirement community reviews, or for more information on taxes and what it is like to retire in Maryland. Here is our review of Ocean City, MD as a retirement community.


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 $394,896 in early 2021, 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


Who Will Like Retirement in Leonardtown

Many government and naval people live here to be close to their jobs. There are many people who have always lived here, while others have moved into the many high-end developments built here. Just about everybody loves its rural and small town feel.

Local Economy Is Driven by

Military services, professional services, education, construction. Patuxent Naval Air Station and supporting industries exert a major influence, which has grown even more in recent years.

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

What people are saying about Leonardtown

It's a pretty neat place
What makes this place special are the nearby Mennonites and their beautiful farms. Plus the classic riverfront downtown. This place is a sleeper!
Posted by jfb48 on March 22, 2007

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