Location: Central St. Mary’s County, approximately one hour south of Washington, D.C.
Average property listing price: Single-family homes located near Leonardtown’s historic central square begin in the $300,000 range, says J. Harry Norris III, appraiser and former Leonardtown mayor. Newly developed single-family homes, most of which follow a neo-traditional style, are priced around $400,000.
Size and population: Approximately 3.25 square miles are home to about 3,300 people, according to Norris.
The history: Colonized in the mid-1600s, Leonardtown is on the list as one of the oldest communities in the state and the country. The town had several other names, including Newtown and Seymour Town, until 1728, when it received its permanent moniker honoring Benedict Leonard Calvert, Fourth Lord Baltimore and governor at the time. Leonardtown’s waterfront location on the Potomac River made it a popular port throughout the 1800s and early 1900s, though the town was subject to some destruction when British forces blocked the Chesapeake Bay during the War of 1812. Leonardtown was designated county seat for St. Mary’s County in 1708, and later became a self-governing municipality in 1858. It has since maintained a town-elected mayor and council.
What’s there: In August 2013, Leonardtown became the first state-designated arts and entertainment district in Southern Maryland. As the title implies, Leonardtown boasts numerous creative and collaborative attractions, including a music school, artist work spaces, galleries, boutiques and art classes.
The Southern Maryland Wine Growers Cooperative opened the Port of Leonardtown Winery in 2009. It's one of only a few cooperative wineries across the country and has received awards for its wines, which are made by combing harvests from more than a dozen Southern Maryland vineyards.
Norris and his wife both grew up in Leonardtown, and it's also where they raised their children. Norris, who served as town mayor for 17 years, says he's seen an increase in the number of families moving here throughout the last decade — conceivably a result of the nearby Naval Air Station at Patuxent River and the College of Southern Maryland's Leonardtown campus.
"There are a lot of changes, but in a lot of respects, it's still the old town that I remember growing up in," he says.
Why Leonardtown: Family-friendly events, including the annual Veterans Day parade, a Christmas tree lighting and First Fridays (monthly block parties with live music), are draws for both residents and tourists. Outdoor activities like hiking, bird-watching and kayaking are also a big part of the lifestyle here, says Laschelle McKay, a resident and town administrator. “It’s a fun place to spend the weekend,” she says.