High on a bluff above Gardiners Bay, with long views stretching toward Orient and Gardiners Island, 4 Dawn Lane on Shelter Island is the kind of home that rarely comes to market and rarely survives intact.
Known as the Osofsky House, the waterfront mansion was built in 1971 by modernist architect Norman Jaffe for fashion executive Meyer Osofsky. It was then expanded by Jaffe himself a decade later.
Now, after a meticulous renovation, the six-bedroom residence is listed for $17.995 million with Sotheby’s International Realty – East Hampton Brokerage agents Nick Brown and Lidia Murphy.
Set on more than 1.5 acres with 175 feet of direct bay frontage, the 5,089-square-foot home has eight full baths and two half baths, plus a host of amenities to entertain guests and owners alike.
The grounds unfold in a series of terraces and cantilevered decks that mirror Jaffe’s signature interplay between geometry and landscape. An extra-deep heated gunite pool anchors the outdoor entertaining areas, which also include a pergola outfitted with a kitchen and fireplace, a tennis court lined for pickleball and coastal-inspired landscaping woven with pollinator gardens.
“Expansions and renovations of Jaffe homes are not uncommon, but what is unprecedented is having Jaffe himself returning to a property and offering a new chapter for the owner’s expanding family,” says Brown, who calls 4 Dawn Lane “arguably one of the most important modernist homes on the East End.”
That second chapter is part of what makes the Osofsky House so significant. Jaffe’s return in 1981 to expand his own design created a layered architectural narrative.
“Many Jaffe homes and other important modernist homes have been neglected and in several cases have been torn down,” Brown says. “The story of this home is quite different.”
In 2020, Benjamin Brougham, senior creative director at Jonathan Adler, purchased the property from the original owners. The brand’s founder, Jonathan Adler, also lives on Shelter Island, and reportedly influenced Brougham’s decision to purchase a home there.
When the Osofsky House came up for sale, Brougham reportedly jumped at the chance to buy it, selling his original Shelter Island home on a whim. What followed was a two-year renovation overseen by Brougham and executed by the East Hampton-based Shoshi Builders.
“The Osofsky House is an iconic modernist home that offers the ultimate in luxury living while honoring the Iconic provenance of Norman Jaffe, sitting high on Gardiners Bay,” Brown says.
Brougham’s intervention was bold but reverent. In an interview with The New York Times, he described relocating the kitchen to the 1,600-square-foot finished basement, transforming it into a gathering hub for his large family. He designed a giant circular dining table made from patchwork panels of cerused oak in an artful counterpoint to Jaffe’s strong architectural lines.
Upstairs, Brougham softened the dramatic effect of a blocky granite fireplace and floor-to-ceiling plate-glass windows with a plush white rug and a semicircular gray bouclé de Sede sofa, blending midcentury gravitas with contemporary warmth. The interiors balance spectacle and livability.
A dedicated guest wing occupies the first level, offering privacy for visitors, while the primary suite sits on the upper floor, oriented to maximize water views. Amenities include a chef’s kitchen, private gym and movie theater.
Brown has built a reputation representing architecturally significant homes. He currently represents 8 Little Ram, another Modernist masterpiece by James Merrell on Coecles Harbor and recently sold 2 Charlies Lane, a Bauhaus-inspired Bertand Goldberg. “For many, Shelter Island feels like a return to the Hamptons of yore,” Brown says. “The Island has made many efforts to protect what they have by limiting the size of new construction and buying back property whenever possible. A third of the Island is preserve and Islanders are very proud of this.”
That ethos of preservation underscores the rarity of 4 Dawn Lane. “There are many unique properties throughout the east end,” Brown says, “finding a luxurious iconic home in mint condition, on the water with all amenities is rare.”
Indeed, the buyer pool is as specific as the house itself. “Homeowners of Iconic Modernist homes often are collectors of Art and their home represents an extension of this,” Brown explains. “This home draws a buyer who understands that they are taking on a stewardship of a home that will certainly bring them joy while remaining a part of the future of understanding of architectural and design excellence.”
Photos: Gieves Anderson & Geir Magnusson
