In addition to the many "in town" neighborhoods that are within walking distance to the Town Square, Leonardtown features several planned developments, such as Singletree, located on Route 5. Just outside of the Leonardtown limits are Avenmar at Breton Bay, Villages of Leonardtown, and Chestnut Hills.

New development has been proposed for Tudor Hall Farms, which has water frontage on Breton Bay and McIntosh Run. The proposal includes 593 dwelling units, a hotel/conference center, restaurant, marina, office park, and signature golf course.

Quality Built Homes is working on a concept plan of single family homes on the Lindsey Farm, off of Route 245.

Marrick Homes will be developing the Clark Farm property located on Route 5.

Leonardtown Landing, located at Leonardtown Wharf, has begun construction of 26 luxury town homes.