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Leonardtown is the county seat of St. Mary's County and one of the oldest towns in Maryland, set at the head of Breton Bay off the Potomac River. A walkable town square, a public waterfront wharf, local shops, and historic homes give it a true small town center, while newer neighborhoods spread out into the surrounding countryside.
Local Insights
We help buyers compare Leonardtown homes by walkability, town water and sewer versus well and septic, HOA rules, water access on Breton Bay, and commute times to Patuxent River NAS, so you can decide with confidence.
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About Leonardtown, MD
Leonardtown is an incorporated town and the seat of St. Mary's County government. Addresses use the ZIP code 20650. The town dates to the early 1700s, and the courthouse, county offices, and the Leonardtown branch of the St. Mary's County Library are all close to the town square.
The town square is the social center, ringed with locally owned restaurants, galleries, and shops. A short walk downhill brings you to the Leonardtown Wharf, a public waterfront park on Breton Bay with a riverwalk, a kayak launch, and open lawns.
Historic Tudor Hall, home of the county historical society, sits near the center of town. MedStar St. Mary's Hospital is just outside town, and Patuxent River Naval Air Station is a common commute.
Town Square
Surroundings
Waterfront
Residential Sections
Access
Location
Leonardtown Real Estate
Leonardtown offers a mix of in town living and country space. Here is a general look at what buyers usually find.
Historic homes and older houses near the square offer walkable access to restaurants, shops, and the wharf.
Townhomes and condominiums, including communities like Foxwell, give buyers lower maintenance options close to town.
Single family subdivisions such as Academy Hills, Leonard's Grant, and Lanedon hold colonials, craftsman style homes, and ramblers, many with HOAs.
Water communities along Breton Bay offer homes with water views, community piers, or private frontage.
Rural properties farther out sit on larger lots with private well and septic systems.
Prices depend on location, lot size, age, and water access. Ask us for recent nearby sales rather than relying on broad averages.
Homes
Options
Living
Communities
Leonardtown Residential Sections
Leonardtown has several named residential sections with different settings and housing characteristics. The following are general sections within the broader community.
Breton Bay
A golf and water community along Breton Bay with homes on wooded lots.
Foxwell
A newer neighborhood near the town center with condominiums and single family homes.
Academy Hills
An established neighborhood close to downtown and local schools.
Leonard's Grant
A residential community near shopping and Route 245.
Lanedon
A subdivision of detached homes a short drive from the square.
Villages at Leonardtown
A neighborhood near town services with newer construction.
Bayside
A water oriented community on the shores near Leonardtown.
St. Clements Wood
A wooded neighborhood with detached homes on generous lots.
Residential section names, property types, and association requirements may vary by listing and legal subdivision. Buyers should confirm each property's subdivision, ownership structure, association documents, fees, and applicable restrictions before purchasing.
Schools & Education in Leonardtown
St. Mary's County Public Schools runs the public elementary, middle, and high schools for Leonardtown. Boundaries can change, so always confirm the assigned schools for a specific address with the school system.
Public Schools
The Dr. James A. Forrest Career and Technology Center, located near Leonardtown, offers career and technical programs for high school students.
Schools that serve parts of the Leonardtown area include:
These are examples, not guaranteed assignments for every Leonardtown address. Buyers should confirm the assigned schools for a specific property with St. Mary's County Public Schools before buying.
Private and Alternative
St. Mary's Ryken High School, a Catholic high school, is in Leonardtown, and several parish and private schools operate nearby. Contact each school for admissions, tuition, and transportation.
Prospective residents should contact individual schools directly for current information.
Colleges
Higher education opportunities in the surrounding region include:
College of Southern Maryland
CSM's Leonardtown campus offers associate degrees, certificates, and workforce training close to home.
St. Mary's College of Maryland
The state's public honors college is a short drive south in St. Mary's City, along the St. Mary's River.
Things to Do and Local Lifestyle
Leonardtown residents have a lively town square, a public waterfront, parks, and community events close to home.
Shopping and Restaurants
The town square and nearby streets hold locally owned restaurants, coffee shops, a bookstore, galleries, and boutiques. Grocery stores and everyday shopping line Route 245 and Route 5 at the edge of town, and the county seat's farmers market brings in local produce in season.
Parks and Outdoor Recreation
Leonardtown Wharf Park offers a riverwalk, a kayak and canoe launch, and views over Breton Bay. McIntosh Run, which feeds Breton Bay, is a popular paddling trail, and county parks and ball fields are close by. Point Lookout State Park and St. Clement's Island are within easy day trip range.
Entertainment and Community Activities
First Friday evenings bring music, art, and open shops to the square each month. The St. Mary's County Fair is held at the fairgrounds just outside town each fall, and the town hosts seasonal events such as a beach party on the square and holiday celebrations. Port of Leonardtown Winery pours local wine right in town.
Getting Around Leonardtown
Leonardtown sits on a few main roads serving St. Mary's County.
Major Roads
Route 5 connects Leonardtown north to Charlotte Hall and Waldorf and south toward St. Mary's City. Route 245 links the town to Hollywood and Route 235, the main road to Lexington Park and Patuxent River NAS.
Traffic conditions vary by time of day, weather, construction, and activity near major employment centers.
Nearby Communities
Leonardtown is close to several St. Mary's County communities:
- Hollywood: A growing community to the northeast with rural lots.
- California: A busy area along Route 235 with shopping and services.
- Lexington Park: Home to Patuxent River NAS and a wide range of housing.
- Mechanicsville: A rural area to the north with larger properties.
- Great Mills: A residential area south of Lexington Park.
- Charlotte Hall: A northern county community along Route 5.
Commuting and Employment
Patuxent River NAS and its defense contractors are the largest employers in the area, and county government, the hospital, and the school system add many jobs in town. Some residents drive to Waldorf, Joint Base Andrews, or Washington, so test the drive at rush hour.
Actual commute times depend on the property's location, workplace entrance, traffic, and schedule. Buyers should test their intended route during normal commuting hours.
Public Transportation and Airports
St. Mary's Transit System runs local bus routes, and MTA commuter buses connect the county with Washington. Look up current schedules before planning a commute around them. Reagan National is the nearest major airport, and BWI Marshall is farther north.
Why Buy a Home in Leonardtown?
1. Walkable Town Square
Restaurants, shops, and galleries are steps from in town homes.
2. Waterfront Wharf
Breton Bay views, a riverwalk, and a kayak launch.
3. Small Town Events
First Friday and seasonal festivals bring neighbors together.
4. Close to Pax River
An easy commute to the area's largest employer.
5. Housing Variety
Historic homes, condos, subdivisions, and water communities.
6. History and Character
One of Maryland's oldest towns, with historic homes and landmarks.
Frequently Asked Questions About Leonardtown MD
What county is Leonardtown, MD in?
Leonardtown is in St. Mary's County and serves as the county seat.
What ZIP code does Leonardtown use?
What public schools serve Leonardtown?
Are there waterfront homes in Leonardtown?
Are there HOA fees in Leonardtown?
Do Leonardtown homes have town water and sewer?
What are property taxes like in Leonardtown?
How far is Leonardtown from Washington, D.C.?
What is there to do in Leonardtown?
How do I get more information on a Leonardtown listing?