Historic Annapolis Building Changes Hands After Decades in Same Family
A historic downtown Annapolis retail property has been sold to a local investor, marking the first arms-length transaction for the building since the late 1960s and representing a significant transition for a family with deep community ties.

Friend Commercial Real Estate has facilitated the sale of a two-story retail building in the heart of Historic Downtown Annapolis, located just steps from City Dock. The transaction, which quietly closed this past fall, involved Lynn Dulin, CCIM of Friend Commercial Real Estate representing the seller, while the buyer was identified as a local investor.
The approximately 1,956-square-foot building had remained in the same family for decades, with this sale representing the first arms-length transaction for the property since the late 1960s. The historic nature of this transfer underscores the changing ownership patterns in downtown Annapolis, where many properties have remained under long-term family control. The property currently houses a local clothing boutique, maintaining the area's retail character during the ownership transition.
"This sale represented the end of a long chapter for a family with deep ties to the Annapolis community," said Dulin. "We're proud to have helped transition this Main Street gem to new local ownership, where it will continue to contribute to the area's vibrant mix of retail, dining, and cultural experiences."
The transaction highlights the ongoing interest in downtown Annapolis commercial properties among local investors, particularly those seeking to maintain the historic character of the area while ensuring continued commercial vitality. The building's prime location near City Dock positions it within one of Annapolis's most desirable retail corridors, known for its tourist traffic and local shopping appeal.
Friend Commercial Real Estate maintains its position as a leading provider of commercial real estate services throughout the region, with additional information available at https://www.friendre.com. The firm's expertise in representing both sellers and buyers in commercial transactions continues to facilitate important property transfers throughout Maryland, Washington D.C., and Virginia.
The sale of this historic property signals continued confidence in the Annapolis commercial real estate market, particularly for well-located retail properties that contribute to the city's unique character. The transition to local ownership suggests that community-minded investors remain active in preserving the downtown's distinctive commercial landscape while ensuring properties remain productive assets within the local economy.