Sean “Sinatra” Reilly’s Quaker Hill Home in Wilmington, Delaware

 A second-floor corridor serves as a gallery for Reilly’s family photos.Sean Reilly’s house is like Sinatra, going from the height of fashion to rock bottom—and, then, making a storied comeback.

When Reilly, an entertainer known for his Frank Sinatra repertoire, moved into a Federal-style house on West Street in the Quaker Hill section of Wilmington in 1983, it already had been through significant ups and downs. 

The original home was built in 1741 in Flemish-bond brick, a distinctive checkerboard of spanners and headers that was an outward display of the prosperity of the owner. But the house was burned out in the city’s race riots of 1968, destroyed but for its stout brick walls. “It had been gutted, totally, and rehabbed before we started renting it,” he recalls.

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High Hopes

In the 1980s, Quaker Hill attracted urban pioneers intent on renovating old row houses. Reilly and his partner, Anthony Mombro, felt at home in a vibrant, inclusive community.

“It was the gay-borhood,” Reilly says.

When his grandmother came by for a visit and told about going to a wake in the house in 1914, Reilly felt he had come home. He rejoiced in worshipping at the nearby Cathedral of St. Peter, seat of the bishop of Wilmington, where his grandparents were married on Valentine’s Day in 1884.

“The history of this place calls out to me,” he says. “In my mind, I can hear the clop of horses’ hooves and the carriages going past.”

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A pair of mohair chairs and a mohair sofa in the living room are from the 1930s.Quaker Hill was established as an historic district by the National Register of Historic Places in 1979. It’s a tiny neighborhood, only 151 buildings on 250 acres, bordered by Tatnall and Jefferson streets, from Second through Eighth streets.

The neighborhood dates back to the early 18th century when Elizabeth Shipley, a Quaker from Philadelphia, persuaded her husband, William, to build a home in Wilmington. The first Friends Meeting House opened its doors in 1738.

George Washington spent time in the house across the street in the summer of 1780. The building was demolished long ago but Reilly can imagine the Revolutionary War general, tall and resplendent in his uniform, striding purposefully down Fourth Street toward Ships Tavern on Market Street.

“Lots of people were born in this house,” he says. “Lots of people died in this house.”

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That’s Life

In 1987, when Reilly bought his home, many of the newcomers were losing their zeal for city life. The neighborhood was not becoming gentrified fast enough to suit investors. He paid $115,000 for the property, $45,000 less than the previous owner paid in 1981.

By the 1990s, most of the urban pioneers had moved out, discouraged by crime and stagnant property values. The gay community was decimated by AIDS.

Reilly and his partner stayed. They added a large wooden deck surrounded by trees, a leafy oasis amid the brick and concrete. They grew in tune with the hum of the city. And the location was close to Shipley Grill, the restaurant Reilly bought in 1989. “I would be miserable in the suburbs,” he says.

In fact, Reilly grew up happily in North Wilmington in a home his father built. Each night, his mother would put the kids to bed, singing the Sinatra classic, “In the Wee Small Hours of the Morning.”

That album is one of his many Sinatra albums and books, stacked neatly atop a sleek bar cabinet with a Rat Pack vibe.


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 In the 18th century, the distinctive checkerboard of spanners and headers were a display of the prosperity of the homeowners.It Was A Very Good Year

In keeping with his affection for nostalgia, Reilly has filled his home with vintage pieces.

The Deco-flavored dining suite includes an angular, rectangular table, chairs with striped silk seats, and a glass-front china cabinet. Reilly turns over a chair to show the label, dated 1931, from Miller furniture in Wilmington.

“Anthony found this at a tag sale in Elsmere for cheap,” he says.

A pair of boxy mohair chairs and a matching sofa, also from the 1930s, are confoundedly uncomfortable. But Reilly loves the way they look.

The geometric, white-glass Art Deco chandelier in the second-floor bath looks like a wedding cake turned upside down. Reilly rescued it from a shuttered dance studio on Market Street that was being gutted.

A wooden child’s desk and chair in the living room came out of an old paint store. There’s a vintage Frigidaire refrigerator in the garage.

“I rarely use it,” Reilly says. “I just enjoy looking at it.”

Throughout the house are prints and photographs of his family and the city, snapshots of moments in time captured in black-and-white. On the back of each frame he has attached a packet filled with pertinent notes, yellowed newspaper clippings and other documentation of the event.

Living in an old house in the middle of a city usually means going up and down lots of stairs because it is more efficient to build up rather than out when acreage is limited. Reilly’s house encompasses five levels: a sub-basement; a lower level with a den and laundry room; the main floor, which houses the kitchen and a combined living and dining space; the second floor, where a bath, bedroom and office are located; and the top floor, an open, unfinished space with jaw-dropping views of the city and beyond.

“You can see clear to Jersey,” he says.


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 Reilly’s collection of Sinatra albums and books are displayed on a bar cabinet.All the Way Home

If the sub-basement’s stark stone walls could speak, they would tell tales of runaway slaves hiding in a tunnel beneath the house, part of the Quaker Hill network on the Underground Railroad.

Reilly found marbles in the basement that belonged to the 12 children of the Lemon family, who squeezed into the house in the early 20th century. He returned the playthings when a few of the siblings came back as senior citizens for a visit.

The 21st century ushered in fresh challenges for both the house and Reilly. His partner died. He buried a sister. His restaurant closed—“and I turned 50.”

Like the neighborhood he loves, Reilly endured. He decided to devote himself to music, while maintaining a practice as an executive recruiter.

“I’m not going to kick myself in the butt at 75 and say ‘Why didn’t I do this?’” he says.


My Way

He also invested in his home, taking advantage of government incentives for improvements made to historic properties. He put $100,000 into a new cedar-shake roof, traditional six-over-six wood-framed windows, a new kitchen and other updates and was rewarded with tax credits of nearly $20,000.

“I would not have known about the opportunity except for a relative,” he says. “It is a mountain of paperwork and a big headache but worth it in the end.”

Today, a black, wrought-iron fence defines a tidy garden and a brick path in front of the house. The elegant, Flemish-bond brick façade shows no signs of the fire that brought the structure to the brink of ruin. And Reilly is still falling head over heels for the city.

“I have 25 windows,” he says. “I can see out—and people can see in.”

He sees himself as the willing steward of an historic home, one in a long line of city dwellers.

“Who is going to live in this house 100 years from now?” he asks. “I’m sure it will still be here.”


Get the Look
  • Find your place in time. Sean Reilly, who loves the music and the vibe of the 1930s, was drawn to the boxy lines and plush look of a mohair sofa and chairs.
  • From trash to treasure. An Art Deco lighting fixture, headed to the landfill, has a new home in a bathroom.
  • Mix and match. In the kitchen, Reilly teamed a carved wooden church pew, circa 1820, with a sleek, 1970s-era glass and chrome table from Shipley Grill, a restaurant he owned in downtown Wilmington.
  • Create your own timeline. A second-floor corridor is a gallery for family photos, including black-and-white photography of the homeowner’s grandfather, John E. Reilly Sr., a state senator, with Harry Truman and Lyndon B. Johnson.
  • Do the paperwork. Applying for government aid that enabled Reilly to receive a handsome tax credit was cumbersome—but well worth the effort.


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