The 8,938 square foot home is now listed for $705,000.
It also has a tunnel underneath that was designed to lead to the nearby Missisquoi River.
Over the years, the property has been used as a ballroom, bed and breakfast, restaurant and bar, school, wedding venue and, most recently, a single family home.
The home was built in 1818 by Captain Steve Case.
In 1870, it was sold to a physician who operated his medical practice on the property.
Another owner is said to have transformed the property into a resort with guest cabins where musicians would perform.
In 1957, a 2,500-square-foot ballroom was added to the property.
This space features vaulted ceilings with exposed beams, a custom bar, stage, updated bathrooms, and even a commercial kitchen.
The house has such an incredible history.
Al Capone is said to have visited the house. It was his stopping point during Prohibition when he was smuggling alcohol across the border into Canada.
From the pumpkin pine floors to the staircase and custom built-ins, the seven-bedroom estate still features many period details.
"Some of the most impressive details from a historical perspective include the nine- and 10-foot ceilings throughout, the chestnut woodwork, the ballroom and the tunnel," Callan said.
The 27-room house has a living room and a parlor with an original marble fireplace.
The nearby library has a separate entrance and can be used as a home office.
The impressive main kitchen was recently remodeled and now boasts custom cabinetry, soapstone countertops, a built-in wine rack, a commercial stove, a walk-in pantry with French doors and a large island.
There is also a balcony and three seasonal rooms with views of the 5.7-acre lot.
Karen has her own ideas for the future use of the house, including again as a charming bed and breakfast.