Welcome to Leonardtown, MD, where your dream home awaits! Explore our extensive listings of homes for sale in this charming Maryland town. Whether you're searching for a cozy single-family home, a waterfront property with breathtaking views, or a brand new construction, Leonardtown has it all. Our team of experienced real estate agents is here to assist you every step of the way. With affordable options and a variety of amenities to choose from, finding your perfect home in Leonardtown is easier than ever. Start your search today and discover the beauty and tranquility that Leonardtown has to offer. Leonardtown is one of the best places to live in Maryland, boasting a rich cultural experience as the only Arts & Entertainment District in Southern Maryland. From historic sites like Leonard Hall Plantation to vibrant outdoor activities along the Patuxent River, Leonardtown offers an exceptional living experience. 

Leonardtown, MD Homes for Sale

If you're in the market for a new home, we've got you covered. Check out our listing of homes for sale below, and discover the perfect place to make your dreams a reality. Just click the "Request More Information" button when viewing the details of that property. We can provide disclosures, past sales history, dates and prices of homes recently sold nearby, and more.

And, if you haven't already, be sure to register for a free account so that you can receive email alerts whenever new Leonardtown listings come on the market. Or are you curious about the value of your current home?

Moving to Leonardtown? 

Leonardtown is a community as well as the county seat of St. Mary's County in Maryland. It's home to about 3600 residents and includes a small historic district, healthcare facilities, and a large public high school. It's bordered by Holly Oaks to the west, Wildewood to the east, Pawpaw Hollow and Breton Bay to the south, and Oakville to the north, even though it's quite a way up to the Oakville border along Highway 235.

Centrally located, Leonardtown is a convenient hub of shopping, dining, historical quaint town square, waterfront trail, and winery. It's close to the Newtowne Neck state park perfect for paddleboarding, row boating, and fixturing as well as the Potomac River, hiking, birdwatching, and hunting.

Leonardtown gets its history as early as the 1650s when the town was originally known as Newtown or Newtowne Hundred. Over the years, people came and went and the historic Leonardtown area remains the only incorporated municipality in St. Mary's County. The town has been experiencing a renaissance of its downtown district with recent openings of several new restaurants, boutiques, retail shops, and businesses. It has several buildings registered as part of the National Register of Historic Places and is known for its fine dining cuisine, fantastic shops and galleries, and close proximity to exploration recreational activities such as the Leonardtown Wharf, the Port of Leonardtown Winery, the Patuxent Adventure Center, and the Macintosh run water trail.

• Leonardtown Official City Site