The purpose of this historic structure report is to provide a set of customized treatment recommendations for 86 Maryland Avenue, in the city of Annapolis, Maryland owned by the American Institute of Architects - Maryland Chapter. This building is a prime example of the dynamic development of Annapolis, and the additive nature of buildings, because the property was created from subdividing a once large, prominent eighteenth-century Annapolis estate into smaller parcels for residential use, and then the building was expanded to provide commercial space. The recommendations are based on a rehabilitation treatment approach, and were determined after thoroughly researching the building’s history, investigating and documenting the existing building conditions, and determining the character-defining elements. They will help guide future projects on the building, and ensure its preservation.