Home & Design: Design Professionals

Keeping an Eye on History

Bob Tortora’s thoroughly modern homes are informed by the past.
By Sam Wilson - August 26, 2019

When the real estate developer Bob Tortora arrived on the East End of Long Island in 1998, Sag Harbor was a quiet town where writers and editors lived. Back then, you could buy a historic house with rickety floors, low ceilings, and drafty old windows relatively cheaply, as long as you had the money and the patience to make it livable. Alternatively, a shrewd buyer might snap up a waterfront house that was built in the 70s, even though it had little going for it apart from its location. Tortora chose the second option. Having long dreamed of owning a captain’s house, he spent the next year and a half transforming what he describes as “a really bad house” at 22 Vitali Cilli Avenue into a stately home complete with a modern-day widow’s walk, a pergola, and its own dock. “Whenever I tell people that my house was built in ’72, they go, 1872? And I say, 1972!” says Tortora. Currently listed with Gioia DiPaolo at Douglas Elliman for $10,500,000, the 4,600-square-foot house served as a template for Tortora’s later work, which, according to DiPaolo, has been widely imitated.

“Bob has a distinctive style which incorporates period elements and modern conveniences with sensitivity,” says DiPaolo. “His houses are never ostentatious or glitzy and they fit right in among existing historic homes. They’re beautiful. Which is why everybody copies him.” 

There’s a lot of his work to choose from. In Sag Harbor alone, Tortora has built or renovated twenty-eight houses, a feat, DiPaolo notes, that has not so much changed the face of the village as preserved it in a good way. “It’s really hard to buy an old house and create exactly what you want. So much is dictated by its proportions and ceiling height.” For a designer-builder like Bob, the challenge is to make a house that’s in keeping with the look of Sag Harbor yet is warm enough and spacious enough for today’s buyer.” 

For inspiration, Tortora, who served four years on the village architectural review board, has always looked to the old captain’s mansions on Sag Harbor’s Main Street. On his first house that meant, as he puts it, “miles and miles of molding.” Tortora explains, “That’s what people did at the time. If you had money, you put it into woodwork. I feel it’s important to be strict about details. You have to keep an eye on history.” In Tortora’s own house, history is reflected in the gleam of the wide reclaimed floor boards while the infrastructure accommodates such mod cons as a highly efficient heating system, central air conditioning, proper insulation, and dozens of windows, the better to enjoy the views of Sag Harbor cove. Though the ceilings are high, its owner rejects the current obsession with thirty-foot-high ceilings. (“Do you really need all that height? Aesthetically, it’s pretty cold.”) Overall, between its sixty-six windows and the cupola on the third floor, which leads to the widow’s walk, the house is suffused with what Tortora describes as “an ethereal light.” “I never want to look down a hallway or walk into a room or not see light,” he says. “To open a door and look through a window is a wonderful thing.” He adds, “A lot of houses nowadays are designed from the inside out — a disaster. Old houses weren’t done that way. Builders and architects tackled the inside only after they got the outside right.” He knows what he’s talking about. Make no mistake, Tortora gets the interior and the exterior right every time.

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