A Shinnecock Estate with Artful Foundations

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When he enlarged the house, O’Brien created an outdoor dining area enclosed by cast-in-place concrete columns, based on black-and-white photos of nearby houses from the turn of the past century

O’Brien (with his dog, Beijo) stuck to a limited palette of stucco and brick, framing privet, and boxwood to make a new garden look like it had grown up with the house

The living room fireplace is bordered by starfish-patterned tiles designed by O’Brien and made in Maine. The painting above the mantle is by the late Hamptons artist Robert Gwathmey; the model is an early 20th century Dutch pond boat.

O’Brien created a new kitchen where friends can watch him cook (the stove is in the island), or gravitate to the media room, which is covered in chestnut paneling to match the living room

O’Brien turned an old porch into a new sunroom, complete with limestone floor, a peacock painting by his friend Beth Rundquist, and iron lawn chairs purchased at tag sales

Combining parts of an old furnace room beneath the house and newly excavated spaces, O’Brien created a wine cellar for 2,500 bottles, most of them Italian

A servant’s room under the eaves became a child’s bedroom, known as the red room (or the Target room for its rug). “Each room has a quirkiness, which I love,” says O’Brien.

A third-floor passageway leads to an Adirondack-style bunk room. “Kids love it,” says O’Brien. “You don’t see them again for the whole weekend.”

In the living room, an early American workbench supports antique iron boccie balls and a trio of still-functional fans. “They looked like a family that belonged together,” says O’Brien of the flea market finds. The large painting, of a Maine afternoon, is by Eleanor Miller

Inspired by a small, academic painting from the Art Students League of New York, O’Brien arranged white roses in his butler’s pantry (which replaced the former small kitchen).

There are no curtains in Tim O’Brien’s house in Shinnecock. One reason is that the windows, with their original 100-year-old glass, are too pretty to hide. Another reason is that the light that comes through those windows is dazzling. Indeed, when O’Brien begins telling the history of the house, the conversation quickly turns to William Merritt Chase, the great American landscape painter. From 1892 to 1902, Chase ran a summer art school in precisely this location. One of the narrowest “necks” on the South Fork, it is bathed in light reflected off bays to the north and south, which inspired Chase to choose it for his studio and school.

Chase’s own house, by the great architect Stanford White, was surrounded by cottages designed for Chase’s students. Only a few of those houses have survived, one of them O’Brien’s. In the 1990s, when he first heard about the shingle-style building, it was about to be torn down. (The owners had already sold the furnishings at an estate sale.) O’Brien fell in love with the house, despite a state of disrepair so extreme, he says, that buying it “would be madness.” Yet he made a full price offer after his first visit—the only way he could be sure it wouldn’t be demolished. And then he began the 17-year process of bringing the house back to life, a saga that was complicated (but also enriched) by lengthy stays in Brazil and Switzerland, where he worked as a financier while collecting furniture and art to bring back to Long Island.

The biggest challenges included restoring the great room, which is paneled in chestnut and feels like being on the inside of a hope chest. Upstairs, he added bathrooms and gave each bedroom a different color, a reminder, O’Brien says, of childhood summers at his grandparents’ beach house in Stone Harbor, New Jersey, where guests were assigned designed color suites, such as “the blue room” or “the yellow room.” The rooms’ surprising configurations—none is a perfect rectangle, and no two are alike—are reminders that the house was designed to be not only functional, but also picturesque.

Once he had restored the existing building, O’Brien began planning a 3,000-square-foot addition meant to match the original. (Before building the foundation and chimneys, he had six stonemasons erect samples in his driveway.) The ground floor contains a media room, reminiscent of the chestnut-paneled great room, a spacious kitchen, and a dining room where most of the seating is on a long banquette. O’Brien tells anyone he invites to dinner to bring their houseguests and says the banquette seats 22 “in a pinch.”

Upstairs, the new wing contains a plush master bedroom suite with east and west exposures. (Both façades have eyebrow windows set into gently curving dormers; O’Brien had them built by a boat-maker, so that their curves would be just right.) As usual, there are no curtains. The transition from the “outdoor rooms” of the garden to the indoor rooms, he says, “has to be seamless.”

And it is, thanks to formal gardens, with paths of herringbone brick and stucco walls that look as if they were there in Chase’s day, that are as architectural as the building itself. (The landscape designer Edwina von Gal provided the initial concept.) The garden seems to flow through the house, and in a sense it does, with a brick-lined underpass beneath the dining room. In the distance are 10 acres preserved by the Peconic Land Trust, a boon not only to the environment, but also to O’Brien’s Portuguese water dog, Beijo, who walks the property with O’Brien every morning, encountering a veritable wild kingdom of deer, turkeys, and rabbits.

If O’Brien moves on, it will be because wanderlust has struck again. He has taken to spending time in Sicily, where he has begun restoring parts of a baroque palazzo, complete with 18th century ceiling frescos. Says O’Brien, whose enthusiasm for renovation and design was nurtured in Shinnecock but now pulls him across the ocean, “I’ve never worked in frescos before, and I can’t wait.”