Leonardtown Homes for Sale 

Included below are homes for sale in Leonardtown. If you would like more information on any of these Leonardtown real estate listings, just click the "Request More Information" button when viewing the details of that property. We can provide you with disclosures, past sales history, dates and prices of homes recently sold nearby, and more.

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Leonardtown May 29, 2023
Avg. DOM
Avg. $ / Sq.Ft.
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35 Properties
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Moving to Leonardtown?

Leonardtown is a community and 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 ways up to the Oakville border along Highway 235.Leonardtown homes for sale

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 Schools

Residents are part of the St. Mary's County public school division and most residents with school-age children are signed to the Leonardtown elementary school, the Leonardtown middle school, and the Leonardtown high school. These schools receive excellent ratings, scores, and reviews by students and parents alike.

"Leonardtown prides itself on our community, academics, and sports. Leonardtown is a high school with wonderful staff that are willing to provide the best experiences for students. Examples of this would be spirit weeks, lunch activities, diverse clubs, monthly events, clean classrooms, and welcoming spaces for all. There is something for everyone at LHS arts, sports, and much more! WE ARE RAIDER STRONG!" - Leonardtown High School Review

Leonardtown Real Estate

There's a variety of homes and styles available in Leonardtown with an average home price of about $380,000. 55% of residents own their own homes and there's a median rent of about $879 as of the publishing of this post in 2020. Home prices are all over the board starting at $120,000 up to $800,000 depending on size, condition, and location. There are several historical homes, fixer-uppers, homes that would make a great renovation project, and brand-new homes. You'll find a wide range of styles, designs, and prices in this extremely popular town. If you're looking for homes on the water, check out Foxwell Point that may offer waterfront homes in Leonardtown.

What do residents have to say?

"Leonardtown is a family friendly area with great schools, close to restaurants, fresh produce, and can ride your bike or walk to activities in downtown Leonardtown. Downtown Leonardtown has family events each season. Wonderful place to live!" 

"Leonardtown is a welcoming town to live in. Leonardtown is continuing to build. Leonardtown has an amazing waterfront park in down town. Leonardtown has many restaurants, a local winery, kayak launch, and local businesses. Leonardtown is in the process of building a new library." - Niche.com

You can see that Leonardtown is a wonderful place to call home. It's not too big, not too small, definitely is its own city in its own right, nestled up against the water, yet minutes to multiple bays, rivers, and surrounding communities and towns in St. Mary's County. If Leonardtown seems like your neck of the woods, browse available listings on my website for free or simply contact me below to get more information on homes for sale in Leonardtown, a virtual tour, or private showing.

Contact a Leonardtown Realtor®

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Image By Elvert Barnes - Flickr, CC BY-SA 2.0, https://commons.wikimedia.org/w/index.php?curid=19351042