Leonardtown is a rapidly growing commuter town outside D.C.
Leonardtown is a Southern Maryland community on the rise, with the population nearly doubling between 2010 and 2020. “It’s one of the fastest-growing municipalities in Maryland,” says Jimmy Hayden , a Leonardtown native and Realtor with Re/Max Realty Group. The town, set on a peninsula hugged by the Potomac River, Patuxent River and the Chesapeake Bay, is now home to around 19,000 people. As for its appeal, Leonardtown offers a revived downtown, water access and proximity to Naval Air Station Patuxent River, which is the county’s top employer. “A lot of people commute to D.C. as well. We’re only about 60 miles south,” Hayden says. In addition to having above-average schools and family-friendly subdivisions, the community is known nationwide for hosting the annual United States Oyster Festival.
New subdivisions are fueling Leonardtown’s growth
Leonardtown has been a hot spot for new home development, with most of the town’s housing built between 2000 and today. Subdivisions such as Clark’s Rest feature Colonial Revival-inspired neotraditional homes, while new construction is rising in the in-development Breton Oaks and Breton Knolls communities. “There’s another big development, Tudor Hall Farms, that’s coming up within the next year,” Hayden says. “It’s going to have public land that’s water-oriented.” Several areas offer waterfront properties, including the established Breton Bay neighborhood. The outlying countryside offers farmhouses, ranch-style homes and split-levels with acreage.
The median price for a single-family home in Leonardtown is around $630,000, well above the national median. Most homes fall between $300,000 and $850,000. Townhouses are available from around $420,000 to $520,000. There are condos downtown, but they don’t go on the market often. A two-bedroom unit sold for about $280,000 in December 2024.
According to FEMA’s National Risk Index, St. Mary’s County has a relatively moderate risk of hurricanes, strong winds and winter weather. Properties along and near waterways have a flood risk, according to the agency’s flood maps.
Above-average private and public schools in St. Mary’s County
St. Mary’s County Public Schools earns an A-minus overall rating from Niche. The district has 26 schools, a virtual academy and a career and technology center serving around 17,000 students. Students can apply to signature academic pathways, such as the Academy of Visual and Performing Arts. Homes within the town limits are zoned for the B-plus-rated Leonardtown Elementary, the A-minus-rated Leonardtown Middle and the A-minus-rated Leonardtown High. Several private schools are in the area, including the A-rated St. Mary's Ryken High, a Catholic high school.
Art, food and community are reviving historic downtown Leonardtown
Leonardtown’s historic downtown is on an upswing, welcoming new businesses and restaurants as community-funded murals add color to century-old brick buildings. This district offers boutique shopping with stores offering a variety of items, from used books and collectibles to gifts and clothing. St. Mary’s County is known for its freshly caught seafood, pulled from the waters of the Chesapeake Bay. Diners in downtown Leonardtown can enjoy the catch of the day at restaurants such as T&Js Cove.
Leonardtown earned distinction as the region’s first Arts & Entertainment District in 2013. The community has a thriving art scene, anchored by the St. Mary’s County Arts Council downtown. Along with galleries and public art initiatives, the community has several creator-focused events each year, including the annual Leonardtown Art Walk, which invites the public to view the works of local artists displayed at businesses around downtown.
A few shopping centers in town offer chain grocers and familiar brands, but national retailers are available less than 10 miles away in California .
The United States National Oyster Festival celebrates the bivalve
Since the 1960s, thousands have visited Leonardtown for the United States National Oyster Festival, held every October at the St. Mary’s County Fairgrounds. Along with eating oysters, attendees can enjoy beer tastings, live music and educational exhibits. “It’s basically everything oyster,” Hayden says. “You can get any kind of oyster—fried, steamed, raw, however you want it—and then they have a lot of vendors and things for the entire family.” The main event is the U.S. Oyster Shucking Championships, in which contestants see who can open 24 oysters the fastest while keeping presentation in mind. The winner represents the nation at the international championships in Galway, Ireland.
Outdoor recreation from the Potomac River to the Patuxent River
Parks dot Leonardtown, ranging from the pocket-sized L Town Alley, which provides a resting spot for shoppers downtown, to the waterside Leonardtown Wharf Park, which offers a boat ramp, floating dock and a boardwalk along McIntosh Run. Warf Park is also home to the open-air Coastal Arts Market, open once a month. Robert Miedzinski Community Park, next to Leonard Hall Recreation Center, is popular with families for its large playground and fields for youth sports. Outside the town limits, waterways hug Newtowne Neck State Park, a destination for kayaking, fishing, hiking and hunting. Hayden says boating on the Potomac and Patuxent Rivers is a popular pastime. “On the Potomac, you can get into Virginia and go to Virginia restaurants. On the Patuxent side, there are a lot of bars and restaurants on the waterway like the world-famous Tiki Bar & Grill on Solomons Island.” Breton Bay Golf & Country Club offers an 18-hole course that’s open to the public.
There are multiple ways to get around Leonardtown
While the outlying areas of Leonardtown are primarily car-dependent, STS Transit provides bus service around the town proper and to California and Charlotte Hall. Commuters have access to several state highways, including Route 5, which heads northwest to Washington , around 60 miles away. Three airports offer commercial flights within 90 miles of Leonardtown: Dulles International Airport, Ronald Reagan Washington National Airport and Baltimore/Washington International Thurgood Marshall Airport. Healthcare is available in town at MedStar St. Mary's Hospital.
