December 4, 2023
Annapolis, US 43 F

Historic Middleton Tavern Building Sold, Tavern to Remain

Middleton 2018

The building that houses Middleton Tavern and two other businesses downtown in Annapolis was sold over the weekend. Rosso Commercial Real Estate Services brokered the off-market deal.

According to a release, the sale closed April 28th, 2023, and the property was purchased by Annapolis Capital Partners (ACP), the Annapolis-based real estate development group led by Naval Academy graduates Cody Monroe & Clinton Ramsden who have been buying up several other historic properties over the past few years.

Situated on the most iconic street corners in Annapolis, the nearly 11,000 SF building is tenanted by Middleton Tavern & two affiliated properties along Randall St. – Annapolis Glassworks & Chesapeake Properties. The group has no plans to change the tenant composition of the building, and each tenant has a multi-year lease agreement in place. The group will not have a role in the management of Middleton Tavern.

“The purchase of this building ultimately reflects our seriousness about investing resources into Annapolis in a way that benefits the community and its visitors,” Clint Ramsden of ACP said. “This building will proudly stand among the historic properties along Annapolis City Dock through meticulous maintenance efforts and investment into the infrastructure of this Annapolis icon.”

Middleton Tavern was host to a galaxy of the nation’s most revered leaders during the period following the American Revolution. George Washington, Thomas Jefferson, and Benjamin Franklin were numbered among its prominent patrons. The Tavern was frequented by members of the Continental Congress meeting in the State House on such historic occasions as the resignation of General Washington’s commission on December 23, 1783, the ratification of the Treaty of Paris ending the Revolutionary War in 1784, and the Annapolis Convention which laid the groundwork for the Federal Constitution Convention.

The building was likely occupied as early as 1740. In 1750, Elizabeth Bennett sold the property to Horatio Middleton, who operated the building as an “Inn for Seafaring Men.”

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