Approved: Courthouse Gateway Apartments
The Leonardtown Planning Board voted 3-1 on Oct. 19 to grant final site plan approval for Courthouse Gateway Apartments, a proposed three-story, 22-unit development at the intersection of Courthouse Drive and Fenwick Street. The decision came more than a year after the project received preliminary concept plan approval in April 2025.
Board member Doug Isleib was the sole vote against the project. The board’s approval included a condition that any street lighting installed must be uniform with the lights already used on Fenwick Street.
Plans submitted by Bumpy Oaks Development LLC show a parking garage on the ground level, with residential units on the second and third floors. Each residential floor would contain 11 one- and two-bedroom apartments.
The project would include parking spaces in the garage and additional spaces outside, including parallel parking along Courthouse Drive. The developer received a parking waiver from St. Mary’s County in June 2026, signed by the County Commissioners, allowing the parallel parking because Courthouse Drive is a county road.
The project required additional approvals from the county’s Department of Public Works and Transportation, the St. Mary’s County Soil Conservation office and the Maryland Critical Area Commission, among other agencies, following the initial concept plan approval.
The development site is mostly cleared, although mature trees and vegetation remain along the northern portion of the property. Plans indicate that most of the vegetation would be removed, with two to four mature trees potentially preserved.
Developer Steve Valentine told the Planning Board in April 2025 that the project would include extensive replanting and landscaping to improve the site’s appearance. The building’s front entrance, facing Fenwick Street, would feature stairs leading to street level, and all apartments would have balconies.
According to the developer’s presentation, the project is expected to generate approximately 12 vehicle trips during peak hours.
The vote reflected differing views among board members about whether the development fits Leonardtown’s downtown character.
Isleib cited the town’s Comprehensive Plan and Downtown Plan, which emphasize preserving the community’s small-town charm and character. He said the project should be appropriately scaled for the approximately one-acre lot.
Board Chair Jean Moulds offered a more favorable assessment, saying the development would improve the corner compared with its current appearance.
Valentine told the Planning Board in April 2025 that he had undertaken redevelopment projects through Bumpy Oaks Development LLC and other entities, including Point Lookout Investments LLC and Washington Street Investments.
Those projects include the acquisition of LaGrande RV Park along Route 5 and improvements to Washington Street Apartments near Dairy Queen in Leonardtown.
Bumpy Oaks Development LLC also appeared before the Planning Commission and County Commissioners during the county’s Comprehensive Plan revision process to request a land-use change for approximately 33 acres off Clark’s Mill Road in Hollywood. The request sought to change the property’s designation from Rural Preservation to Residential Low Density and incorporate it into the Hollywood Town Center. The request was denied by the County Commissioners on October 20.
