Apartments & Assisted Living in Leonardtown
Two Developments Coming Soon
Concept rendering of St. Mary’s Assisted Living
Originally approved in 2023, the St. Mary’s Assisted Living & Memory Care Facility recently received a 12-month extension on its permits, allowing developers more time to begin construction. While the delays have required formal approval from the town—residential permits typically expire after 12 months if construction hasn't begun—the project continues to move forward.
Plans for the facility outline a 32-unit residential building that will include accommodations for residents with memory care needs. An estimated staff of 15 will support the day-to-day operations, and 27 parking spaces will be provided, including two that meet ADA accessibility standards.
Concept site plan: St. Mary’s Assisted Living
The facility will be constructed on just a small fraction of the 15.5-acre lot. Over 14 acres will remain wooded, and 5.5 acres of that land are under a conservation easement, ensuring permanent protection. A landscaped “wander garden” at the rear of the building will provide a safe, outdoor area for residents to enjoy. The site borders natural stream and vegetation buffers, all of which will be preserved, along with a 30-foot public right-of-way on the eastern edge known as “Old Clay Hill Road,” long since abandoned. The property lies almost entirely within the state-designated Critical Area.
While the care facility project has been quietly advancing, the proposed Courthouse Gateway Apartments have sparked far more visible discussion—particularly during a recent Leonardtown Planning Board meeting where the project’s concept plan was narrowly approved by a 2–1 vote.
The apartment complex is the vision of developer Steve Valentine, operating under Bumpy Oaks Development LLC. Valentine is no stranger to Leonardtown and the surrounding region. Through other entities like Point Lookout Investments LLC and Washington Street Investments, he’s undertaken various redevelopment projects, including the acquisition of LaGrande RV Park on Route 5 and upgrades to Washington Street Apartments near Dairy Queen.
The project would sit on just under an acre of land—0.99 acres to be exact—and feature 22 luxury apartments across three stories. Six units are planned as two-bedrooms, with the remaining sixteen as one-bedrooms. The building will include 45 parking spaces at street level, with 16 outdoor, 24 under the building’s two stories, and 5 parallel spaces on Courthouse Drive. An elevator will service the units, and a pedestrian skywalk will connect the second level (first apartment floor) directly to Fenwick Street near the town’s “Downtown Gateway” sign.
Valentine described the project as an upscale addition to Leonardtown, with unit sizes ranging from 800 to 1,100 square feet, with rents starting around $2300 for a one-bedroom and up to $2600 for two.
The most contentious part of the project centered on how stormwater runoff would be handled. The proposed plan routes runoff onto adjacent town-owned land across Courthouse Drive—an area already suffering from drainage problems that lead toward the wastewater treatment plant. Town Planning Coordinator Mike Bailey acknowledged the issue, with Town Administrator Laschelle McKay noting that the town has already spent significant funds trying to manage the runoff problem.
Suggested edits to stormwater management plan. Red “X” where current outfall is planned, with blue line showing water diverted underground along Courthouse Drive to Fenwick St. (Edits added by author).
As designed, water flowing downhill between Fenwick Street and Park Avenue would divert to the north and south sides of the building. Runoff to the south would run under the parking lot, through a pipe to a berm along town property. Bailey’s solution was to redirect the water from flowing toward the berm via pipe over to Fenwick Street, and then along the existing drainage system. The developers, citing rising construction costs, argued that the stormwater plan as submitted was adequate and that further changes would make the project less feasible financially. Fenwick Street will see some disturbance to provide access to a water line for the apartment building.
Current view from Fenwick St.
Nearly every mature tree on the plot would have to be removed to allow for grading and construction. Only four out of approximately 25 trees would remain. This prompted strong criticism from Planning Board member Doug Isleib, who voiced frustration over the environmental cost of the development. With a building this size “there’s too much damage being done,” Isleib said.
The steep 60-degree slope on the property would need to be cut down to about 30 feet to create a flat foundation—a process known as benching—and that the slope was too erosive in its natural state to be safely preserved.
Board Chair Jean Moulds offered a more pragmatic perspective, suggesting that fast-growing replacement trees could quickly restore the canopy. The developers seemed supportive, saying “In three to four years they could be over the roofline.” Still, Isleib remained unconvinced, particularly given the visual importance of the site. “This is a really important plot of land as an entryway to the town,” he said.
The final vote reflected the board’s division: Isleib wouldn’t second member Andrew Ponti’s motion to approve the concept plan, leaving Moulds to step in. The plan passed by a 2–1 margin.
