Modernism for sale: a Norman Jaffe-designed icon on Shelter Island hits the market

Throw a stone in Long Island and chances are you’ll hit a residence with some architectural distinction. From a purely mercenary point of view, the region was awash with tear-downs, much to the chagrin of design enthusiasts.

The region’s gradual elevation into a rarefied retreat world for the most moneyed New Yorkers has put a bit of a damper on innovation, with many of the more modest structures built in the 60s, 70s and 80s now lost for good.

Only those structures that were built big in the first place have managed to make it to architectural maturity, with all the necessary protections that affords.

That’s the case with this stunning Norman Jaffe design on Shelter Island. The Osofsky House was commissioned in 1971 by fashion mogul Meyer Osofsky. Osofsky's sportswear label Aileen was named for his wife, a noted philanthropist in both New York and Long Island.

The Osofskys briefed Jaffe to create a spectacular modern residence, one of three houses the architect designed in this spot on Shelter Island (the Seidler House and Betty Jacobs House). The architect, who drowned off Bridgehampton in 1993 aged 61, was the consummate exponent of his own take on rustic American modernism. Living and working in the region, he built a total of 50 projects in and around the Hamptons.

Aileen and Meyer had a long association with the house, which was further expanded and updated by Jaffe in 1981. The house now has six ensuite bedrooms, including a separate guest wing, with other amenities including a gym, cinema room, heated pool and catering kitchen.

In 2020, the house was sold to interior designer Ben Broughman (who had admired the house from afar for many years before acquiring it) and his then partner Waheed Alli.

The subsequent renovation brought the house bang into the 21st century, with a mix of eclectic contemporary decoration, updated facilities and amenities and a refreshed sense of colour and pattern that pays homage to the house’s 70s heyday.

The setting, on the north-eastern shore of Shelter Island, is spectacular, with Jaffe’s design providing a staggered cascade of balconies overlooking the beach at Gardiners Bay. A naturally planted garden enables the house to blend perfectly into the shoreline, with vertical stone piers and chimneys pierced by the horizontal roof structure.

The latter belies the strong influence of Frank Lloyd Wright on Jaffe’s work (the balconies are strongly reminiscent of Wright’s Fallingwater), with the monumental stonework carried through to the interior, notably in the fireplaces and flooring, paired with floor to ceiling windows (more of those ocean views), wooden cladding and bold patterned fabrics.

The updates also included some light reconfiguration of the plan, with a new ground-level kitchen and better access to the exterior across the house’s many levels.

In total, the Osofsky House has an area of 6,715 square feet, with 175 feet of shoreline frontage. The entire plot, which includes a tennis court and two-car garage, measures 1.7 acres. It’s therefore unsurprising to find that the near $18m asking price makes it the current most expensive listing on Shelter Island.

The Osofsky House is on the market with Sotheby’s International Realty for $17.995m, SanMiguelSothebysRealty.com