What do a bootlegger, a group of friars and the CEO of Phillips Foods have in common? All three made their home across the Severn River from Annapolis, Md., in a mansion with a quirky history.

The Georgian-style mansion, modeled after the James River Plantations in Virginia, was built in 1922 by E. Bartlett Hayward, who made brass shell casings for French guns during World War I and was a bootlegger during Prohibition.

“We’ve been told that the tunnels that lead down from the house to the dock were used for bootlegging,” said Steve Phillips, CEO of Phillips Foods and Seafood Restaurants, who owns the Anne Arundel County estate with his wife, Maxine Phillips. “We’ve also been told the tunnels may have been here earlier as part of the Underground Railroad to hide slaves escaping to freedom.”

Distinguished homes for sale in the D.C. region

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Annapolis-area mansion | This nearly 100-year-old Georgian-style mansion, on a Severn River estate near Annapolis, Md., was restored by the owners. (Sean Shanahan)

In 1945, the Catholic Church purchased the property for a friary, which at one point housed as many as 60 Franciscan friars. The friars added a dorm, a bowling alley in the basement of the main house, a tennis court and several outdoor pizza ovens.

“When Steve sent me on a scouting mission for a property on the Severn River with lots of land for privacy, I ignored this house at first because it was listed as having 26 bedrooms, which was way more than we would ever need,” Maxine said. “But privacy was key to us, along with access to the river for boating, so I looked at it as a possible teardown.”

Instead, the Phillipses fell in love with the house, despite the raccoons living in the fireplaces.

“The architecture was beautiful, and it was built with such quality that there were no leaks or anything even though it had been empty for decades,” Maxine said. “There were so many delightful elements to the house that we decided to take a hybrid approach and save some of it while adding our own taste to the property.”

The Phillipses spent more than five years restoring and renovating the property after they purchased it in 2002.

“We respect the unique history of this house and realize that you wouldn’t be able to build something like this today,” Steve said. “We restored all the handmade moldings, which function like a ribbon that winds throughout the more formal main house and the newer wings.”

The Phillipses took samples of the house’s hand-carved fireplace mantels to Italy to match the marble for restoration and found pine boards to blend with the preserved antique wood floors. They converted the chapel to an entertainment space.

“We took out the confessional booth in the chapel because I was afraid I’d be in it all the time,” Steve said.

Although the property has been used for large parties and weddings, the Phillipses said they value it most for its privacy.

“We’re very private people and don’t entertain a lot,” Steve said. “Even when we do have a larger gathering, the house is so large that it doesn’t seem like a lot of people.”

That emphasis on private moments is clear when the couple talks about their favorite spaces. For Steve, the teak tea pavilion in the woods offers space for quiet meditation. The pavilion was built in India, disassembled and reassembled at the Phillips estate.

The couple has traveled extensively in Asia and enjoyed bringing artistic elements and special materials from that part of the world to their home. The tea pavilion is a great place for messy crab feasts, and yet it is elegant enough for a wedding reception, Maxine said.

“I love the billiards room because I’m a sailor and we designed the space to look like an old ship’s galley with wood walls and a wood ceiling,” Steve said. “There’s a huge fireplace, which is great to come home to in winter, and the pool table is 100 years old.”

Maxine, who loves to read, said she appreciates the library, which has restored wood floors, mahogany- and oak-paneled walls and oak shelves.

“I was recently in law school, and that was my favorite place to study, in front of the fireplace,” Maxine said.

She also loves her glamorous bathroom in the primary bedroom suite, which has his-and-hers bathrooms.

“Everyone is surprised I love it so much because it’s not really my style, but I love the light cream limestone floor, the antique sterling silver chandelier and the huge marble tub,” Maxine said. “You can see the roof garden and trees from the windows, too.”

Other spaces the couple love include the spa, which replaced the friars’ bowling alley, the outdoor infinity swimming pool and the outdoor kitchen.

“We tried not to do formal gardens because we prefer the woods and trees and wilder grounds,” Maxine said. “We added a funicular to make it easier to get to the dock where we keep our boats at the bottom of the hill.”

The couple converted the original gatehouse to a guesthouse and kept the adjacent meadow for croquet and impromptu softball games with the family.

1604 WINCHESTER RD., ANNAPOLIS, MD. (mail address)

$24.9 million

Features: The main house has seven bedrooms, 13 bathrooms, 11 fireplaces, a formal dining room, a formal living room, a ballroom, a conservatory, a family room, a library, a music room, an indoor spa, a game room and a wine cellar. The property also has a guesthouse, a teahouse, a nine-car garage, a roof garden, a swimming pool, a tennis court, terraces, a fountain and a funicular to the private dock on the Severn River.

Approximate square-footage: 35,000

Lot size: 23 acres

Listing agents: Brad Kappel and Dave DeSantis with TTR Sotheby’s International Realty