1604 Winchester Rd, Annapolis: Inside The $12.5 Million Friary Mansion
The Friary at 1604 Winchester Rd Annapolis MD is one of the most remarkable historic estates featured on RivonHome. Set across 22.52 acres along Maryland’s Severn River, the 35,435-square-foot Georgian Revival home was built in 1922 and features seven bedrooms, eight full bathrooms, and five half baths.
The estate blends grand architecture with peaceful waterfront living, private grounds, and a rich history that continues to make it unforgettable.
1604 Winchester Rd Annapolis MD Location
- Full Address:Annapolis, Maryland, 21409
1604 Winchester Rd sits in Annapolis, Maryland, 21409, inside Anne Arundel County. The property overlooks a wide bend of the Severn River, about 10 minutes from downtown Annapolis, 30 minutes from Baltimore, and 45 minutes from Washington, D.C. You get privacy, water, and a short drive to the capital, all at once.
1604 Winchester Rd Annapolis MD Tour
As Stefano Schiavon from RivonHome, I had the opportunity to tour this remarkable 1604 Winchester Rd Annapolis MD estate with my friend Dave, who specializes in waterfront real estate. As we turned off Winchester Road, the trees opened to reveal beautiful brickwork and river views.
Inside, the impressive rotunda, historic chapel-turned-ballroom, and connected wings created a fascinating blend of architectural eras. Even the boathouse felt extraordinary, making the entire estate an unforgettable experience in history, design, and waterfront living.
Inside 1604 Winchester Rd Annapolis MD Interior and Other Features
Walk past the front door of 1604 Winchester Rd Annapolis MDand every room tells a different chapter, from monastery chapel to modern family retreat.
Grand Entrance
Step into the main core of 1604 Winchester Rd Annapolis MD and you land on original heart pine floors laid in 1922. The foyer arch moldings survived every renovation, and a limestone rotunda with a conservatory and atrium connects the two wings. Light pours in from above, and the brick Georgian façade outside gives no hint of the airy, almost church-like space waiting behind the front door.
Bedrooms
1604 Winchester Rd Annapolis MD holds 7 bedrooms across its wings. The primary suite has two sitting areas, each with its own fireplace, a separate bright bedroom, dual custom bathroom and dressing rooms, a walk-in closet, and a morning room that opens onto the roof garden. Two more bedrooms sit on the second floor, each with a private bathroom and its own sitting area.
Bathrooms
Listings show 8 full baths and 5 half baths, 13 total. The primary suite alone carries dual dressing-room bathrooms finished to match the rest of the home’s craftsmanship. Materials lean toward stone and hand-finished woodwork rather than anything flashy, matching the restrained, historic feel the Phillips family kept throughout the renovation.
Living Spaces
Across 35,435 square feet, you get formal rooms in the central core and looser, casual space in the wings. The chapel once used by Capuchin friars is now a ballroom, with a limestone fireplace, herringbone teak floors, and arched double doors opening onto a terrace. A separate guest wing has its own spacious common room for entertaining.
Kitchen
1604 Winchester Rd Annapolis MD carries both a gourmet kitchen and a separate catering kitchen, a setup built for real entertaining rather than quiet weeknights. The layout supports a social flow between cooking space and the main living areas, so a host can work the room and the stove at once. It is a kitchen built for parties, not solo meals.
Special or Unique Spaces
This is where the house gets strange, in the best way. There’s a wine cellar, an indoor spa with a pool, an Asian tea house on the grounds, and a billiard room hand-carved in teak by artisans in Indonesia. Underneath it all sits a tunnel and vault once tied to Prohibition-era rum running, according to the listing agent.
Security & Privacy
23 private acres buy you real distance from the road, and the tree line does the rest. A six-slip private dock with a boat lift sits below the bluff, reached in part by a funicular railway. Nine garage bays handle the cars. It’s the kind of privacy that comes from land and water, not just a gate.
How Much Is 1604 Winchester Rd Annapolis MD 21409 Currently Worth?
The number here has moved a lot. The estate first listed near $32 million in 2012, dropped to $28.8 million, then $24.9 million for a no-reserve auction in 2021, and later returned to market at $19.995 million. Records show it sold on December 1, 2025, for $12.5 million, a steep drop from its early asking price, closing out the Phillips family’s ownership.
Additional Properties Owned By The Phillips Family
Public records and coverage of the sale point to this Annapolis estate as the Phillips family’s primary and most documented residence. I could not confirm other named properties tied to Steve and Maxine Phillips in the sources I reviewed, so I won’t guess here. If that changes, I’ll update this section with a proper source.
Where Does The Phillips Family Live Now?
With the Winchester Road sale closed in December 2025, the Phillips family’s next home is not public information yet. Before the sale, they split time between this Severn River estate and their work running Phillips Seafood, a business that’s kept them rooted in the Maryland and Baltimore area for decades.
Does The Phillips Family Own A Private Jet Or Luxury Vehicles?
I did not find reliable, sourced details about a private jet or a specific vehicle collection tied to Steve and Maxine Phillips. Rather than guess, I’ll leave this one open. What is documented is a nine-car garage on the property itself, built for a serious car collection, whatever fills it.
Phillips Seafood Career Overview
Industry: Seafood restaurants and packaged seafood products. Company: Phillips Seafood, family-owned since 1914. Achievements: Three restaurant locations across Maryland, additional airport locations, and seafood products sold in grocery stores nationwide. Milestone: Steve Phillips, as company CEO, used proceeds from the business to buy and restore the Winchester Road estate.
Phillips Family Net Worth: How Much Money Do They Have?
I did not find a verified, sourced net worth figure for Steve and Maxine Phillips in my research. What is documented is their spending on this property: a $2.5 million purchase in 2002, followed by a renovation that reportedly ran to around $32 million, well above their original $14 million budget for the restoration.
Conclusion
Walking this property with Dave, I kept thinking about how many lives one house can hold, arms dealer, friary, boarding school, family home, all inside the same brick walls. And here’s the highlight joke: with a kitchen built for catering-scale crab cake production, maybe they should have called it “The Fry-ary” instead. Clients ask us for this exact blend of historic bones and modern luxury constantly, and this tour is proof it’s not just a trend.
FAQ About 1604 Winchester Rd Annapolis MD
What is 1604 Winchester Rd Annapolis MD known for?
It’s known as The Friary on the Severn, a Georgian Revival estate built in 1922 that later served as a Capuchin friary and a short-lived boarding school before becoming a private family home.
Who owns 1604 Winchester Rd Annapolis MD 21409?
Steve and Maxine Phillips of Phillips Seafood owned the property from 2002 until its sale on December 1, 2025. Public records had not confirmed the new owner’s name at the time of writing.
Who is the current owner of 1604 Winchester Road, Annapolis, MD?
Sale records show the property closed in December 2025 for $12.5 million, but the buyer’s identity was not listed in any of the sources I reviewed, so I can’t confirm a name here. I looked for a Reddit discussion naming the buyer and didn’t find a reliable answer there either, so I’m disclosing that gap rather than guessing.
