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Home of the Week: This Former Bootlegger’s Lair Is Now a Stunning $24.9 Million Maryland Mansion

You can still take the secret escape tunnel down to the waterfront.

Annapolis Mansion Photo: Sean Shanahan Photography

During the past 92 years, this palatial home has played host to a former bootlegger and gun runner, Capuchin monks, a Japanese teaching academy and, more recently, a Maryland crab tycoon.

Now, the sprawling estate called Friary on the Severn, set on 23 private wooded, waterfront acres minutes from downtown Annapolis and with views of the US Naval Academy, is ready for a new owner.

Among the estate’s multitude of jaw-dropping features; spectacular 270-degree views of the picturesque Severn River, a six-slip private dock accessed by a funicular railway, a grand ballroom, nine-car garage, an Asian tea house, and, naturally, a secret tunnel.

“This is one of the most distinctive, most unusual, most architecturally beautiful estates offered for sale on the East Coast,” says broker David DeSantis, of TTR Sotheby’s International Realty, who shares the listing with colleague Brad Kappel.

A well-to-do Baltimore foundry owner supposedly built the sprawling brick mansion in the Roaring ’20s, styling it after Virginia’s gracious James River plantations. Legend has it that in addition to his day job, he was running guns and selling bootleg liquor on the side. He used the estate’s waterfront to bring in the contraband or as means for a quick escape from the law.

Annapolis Mansion

The stately home once housed both monks and a gun runner.  Photo: Sean Shanahan Photography

That might account for the secret tunnel that still runs from a hidden vault under the house, accessed through the wood-paneled games room, down to the river.

After he sold it in 1945, the estate was eventually bought by the Catholic Church and converted into a friary, housing as many as 60 Capuchin monks. The current home’s elegant ballroom, with its wooden vaulted ceilings and towering arched windows, served as the chapel.

Annapolis Mansion

Original architectural details like the fireplaces and windows were preserved.  Photo: Sean Shanahan Photography

When the friary was disbanded in the 1980s, the estate was sold to the Yokohama Academy, with plans to turn it into a boarding school for Japanese students. Objections and lawsuits from local residents eventually quashed the plans.

Fast forward to 2002. After being left empty and abandoned for more than a decade, the now-derelict home was snapped-up by Steve Phillips, CEO of Baltimore-based Phillips Seafood for $2.5 million. Founded in 1914, the family-owned business is the leading importer and distributor of crab meat in the US.

Annapolis Mansion

The formal dining room.  Photo: Sean Shanahan Photography

Phillips and his wife Maxine spent the next five and a half years—and a reported $30-plus million—rebuilding, restoring and renovating the historic property.

“The attention to detail and emphasis on proportions and craftsmanship are unparalleled. The home, as it is today, is the result of a mammoth and complex renovation that brought it back to its classic Georgian style,” explains Sotheby’s DeSantis.

Annapolis Mansion

The office.  Photo: Sean Shanahan Photography

A long, meandering driveway leads from security gates to a large rectangular motor court in front of the home’s imposing facade. Inside, there’s a total of seven bedrooms, eight bathrooms and 11 fireplaces.

One of the home’s true architectural gems is its dramatic, sweeping dual staircase that leads to a huge, second-floor circular mezzanine. Floor-to-ceiling windows flood the space with light.

Annapolis Mansion

The renovated kitchen.  Photo: Sean Shanahan Photography

The home’s maritime connections—the Phillipses are passionate and accomplished sailors—are reflected in an exquisite wood-lined reception room. With its planked ceiling, varnished wood floors and nautical artwork, it’s a cozy spot to curl up with a seafaring read.

The former chapel has been transformed into a huge, formal dining room that can double as a ballroom. What was once a monks’ dormitory is now a serene, Asian-influenced indoor spa with a pool.

Annapolis Mansion

The ballroom was once a chapel.  Photo: Sean Shanahan Photography

At the rear of the home, raised up above the lawns, is a 60-foot-long, infinity-edged outdoor swimming pool. But skinny-dippers beware; the home’s lower-level Zen relaxation room features two large circular windows with underwater views.

Interestingly, the estate was first put on the market eight years ago for $32 million, but eventually removed after Phillips’ reluctance to see the property go. Now, with children grown and gone, it seems the couple is committed to moving on.

Annapolis Mansion

The master suite.  Photo: Sean Shanahan Photography

Annapolis Mansion

More contemporary touches are scattered throughout the home.  Photo: Sean Shanahan Photography

Annapolis Mansion

The garage can house an entire collection.  Photo: Sean Shanahan Photography

Annapolis Mansion

The indoor pool.  Photo: Sean Shanahan Photography

Annapolis Mansion

The wine cellar and tasting room.  Photo: Sean Shanahan Photography

Annapolis Mansion

The cozy sitting room.  Photo: Sean Shanahan Photography

Annapolis Mansion

The outdoor infinity pool.  Photo: Sean Shanahan Photography

Annapolis Mansion

The beautifully landscaped grounds.  Photo: Sean Shanahan Photography

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