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St. Mary's Watershed Park

St. Mary's Watershed Park

Leonardtown, is the only incorporated municipality in St. Mary’s County. Rich with history, Leanardtown is the perfect mixture of old and new. Over the last decade the town has opened new restaurants and shops, revamped its waterfront as well as several beautifully designed housing developments. 

Find the newest homes for sale & real estate listings in Leonardtown!  In this competitive market it’s important to stay on top of the newest listings & to alert us on anything you would like to see.  If you would like more information on any of these Leonardtown homes for sale, just request information on the listing details page of the property. 


Sunset at Leonardtown Wharf Park

Sunset at Leonardtown Wharf Park

Leonardtown is a quaint town filled with shopping, restaurants, a winery, and a water trail. Residents can enjoy hiking, birding, and hunting in Newtowne Neck State Park. The Leonardtown Wharf Park as well as the Port of Leonardtown Park/ Mcintosh Run is a peaceful and beautiful waterfront attraction, beautiful walking paths as well as launch sites for kayaks, canoes, and stand up paddle boards, rented through the Patuxent Adventure Center right here in Leonardtown.

If you want to escape the outdoors and learn a little about Leonardtown’s rich history, you can do so inside of Tudor Hall, the oldest building in Leonardtown. Another historic attraction is The Old Jail. A cannon from The Ark, one of two ships that first brought colonists to Maryland, and later used to defend St. Mary's City, is displayed on the grounds. The museum also serves as a county visitor information center. 

Take a break from the history and discover the Port of Leonardtown Winery, which is a stop on the Patuxent Wine Trail. Sit back, relax, and allow the winery’s knowledgable pourers to take you through a tasting.


This community is home to one public elementary school, many private elementary and middle schools, one public middle school, and Leonardtown High Schools. Leonardtown is part of the St Mary's County School District.