A Shelter Island waterfront estate originally designed by the famed architect Norman Jaffe sold for a record-setting figure — $15,995,000.
Nick Brown and Lidia Murphy of Sotheby’s International Realty’s East Hampton Brokerage represented the sellers of the residence set on 1.7 acres with 175 feet of frontage on Gardiner’s Bay.
“What a privilege it was to represent 4 Dawn Lane, the Osofsky House,” says Brown. “To spend time in a Norman Jaffe that has been lovingly maintained and elevated by the incredibly talented Ben Brougham has been a professional high. I am confident the new stewards understand the importance of the home and will continue to celebrate Jaffe’s creation.”
This new record for a residential home on the small island blew the old record out of the water, as 4 Dawn Lane sold for a whopping $3,045,000 more, or about 23.5% higher, than the previous record, set in 2023. The Snyder House at 2 Charlie’s Lane, a 3.4-acre home property that boasts panoramic views of West Neck Harbor, traded for $12.95 million, at the time besting the previous record by more than half a million. Back in 2008, the 8,500-square-foot house at 1 Shorewood Court, on a 7.8-acre peninsula, on a bluff overlooking Ward’s Point, traded for $12.4 million.
The median sales price on Shelter Island is approximately $1.2 million as of March 2026, according to Redfin. Sales in the niche market were down 36.6% year-over-year, but because of a low transaction volume on the island, that can be a misleading figure.
Still, real estate on Shelter Island does not reach the heights of the Hamptons market. Last year, the biggest sale on the market was $12.85 million. While there was scuttlebutt that the transaction might break the small island’s real estate record for a single-family home, the 3.4-acre property at 1 Pandion Road fell just a hair short of breaking the 2023 record.
As for the home at 4 Dawn Lane, it is located in Hay Beach, a neighborhood on the northern section of the island, not far from the Gardiner’s Bay Country Club.
The home was first imagined by the Osofsky family and originally designed by Jaffe in 1971. A decade later, he expanded the home, “a rarity among his works,” according to the listing.
Jaffe, an architect noted for his contemporary, sculptural homes, designed more than 600 projects in his 35-year career, 50 of which were in the Hamptons, where he became known for his pioneering designs before he died in 1993.
The architectural integrity was preserved despite recent renovations that added more modern comforts.
There is 6,715 square feet of space, including the finished lower level, along with six en suite bedrooms, eight full baths and two half baths, split between the main home and the dedicated guest wing. The chef’s kitchen provides space for entertaining, while the home offers several amenities, such as a movie theater and a private gym.
Cantilever decks offer incredible views toward Orient and Gardiner’s Island.
An extra-deep heated gunite pool sits waterside with an entertaining pergola nearby featuring an outdoor kitchen and fireplace.
The property also holds a tennis court with pickleball lines.
Coastal-inspired landscaping and pollinator gardens can be found throughout the grounds.
Check out more photos below.
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