A 1970s Waterfront Home Designed by a Renowned Hamptons Architect Could Set a Record Price
Geir Magnusson / Sotheby’s International Realty
Beds: 6 Baths: 8 Full, 2 Partial Living Area: 5,089 ft² (472.78 m²)
A waterfront estate on Shelter Island designed by architect Norman Jaffe is on the market with Sotheby's International Realty for $17,995,000 (~€15.7M), and positioning itself to set a new price record for the island.
Jaffe is widely regarded as one of the defining modernist architects of the Hamptons, and surviving examples of his work—particularly those that have been carefully preserved—are increasingly valued within a niche segment of the market that prioritizes architectural authorship and provenance.
Comparable architect-driven properties—particularly mid-century and modernist homes—have in recent years been marketed and, in some cases, transacted at premiums relative to similar homes without a well-known architect, reinforcing a broader trend toward treating certain properties as collectible real estate.
The property—known as the Osofsky House—sits on approximately 1.7 acres with roughly 175 feet of direct water frontage. The house was originally commissioned in 1971 by Meyer Osofsky and Aileen Osofsky, for whom it takes its name, and is considered a strong example of Jaffe’s work, defined by its sculptural cedar forms, low horizontal profile, and close integration with the surrounding coastal landscape.
By the time the home was designed, the principles of organic architecture shaped in part by figures such as Frank Lloyd Wright were already well established in American practice. Working within that tradition and adapting it to the Hamptons landscape, Norman Jaffe designed the Osofsky House, whose early sketches bear a striking resemblance to Wright’s Fallingwater, designed in 1939.
Norman Jaffe designed the Osofsky House, whose early sketches bear a striking resemblance to Wright’s Fallingwater, designed in 1939.
Notably, Jaffe returned to the property in 1981 to design an expansion—an uncommon occurrence in his body of work, where later alterations were often carried out without the original architect’s involvement. That continuity further reinforces the home’s architectural integrity and places it among the more significant surviving examples of his residential designs.
The current owners, interior designer Ben Brougham and media executive Waheed Alli, purchased the home in 2020 for approximately $7.15 million. Over the following years, they undertook a comprehensive restoration and upgrade, repositioning the property as a turnkey waterfront compound. The result is a residence that blends architectural pedigree with contemporary luxury, including a pool, tennis court, multiple outdoor living areas, and amenities designed for extended summer use.
At its current asking price of approximately $17.995 million, the property is among the most expensive ever offered on Shelter Island. Public records indicate the island’s previous high sale was approximately $16 million, suggesting that a transaction near the current ask would establish a new benchmark for the market.
Shelter Island is physically separated from the Hamptons and accessible only by ferry. It is one of the least developed luxury markets in the region, with roughly one-third of the island preserved as protected land. Strict zoning and limited new construction have constrained supply, while the absence of large-scale commercial development, nightlife, and direct highway or rail access has kept the market smaller and less liquid than nearby East Hampton or Southampton. As a result, transactions above $10–15 million remain relatively rare, with waterfront and acreage serving as the primary drivers of value.
The property is currently listed as pending, indicating that a buyer has been secured, though final closing details have not been publicly reported.
As of early 2026, no completed sale has been publicly recorded. The transaction, once finalized, will provide a clearer indication of pricing at the upper end of a relatively thin and illiquid market.
All photos Geir Magnusson / Sotheby’s International Realty. See even more photos on Sotheby's International Realty.
