The 8.22‑acre oceanfront compound that once belonged to fashion designer Calvin Klein is on the market again, listed at $165 million as of June 2024. Its price nudges it close to the Hamptons’ all‑time record set by hedge‑fund manager Barry Rosenstein, who paid $147 million in 2016.
Klein acquired the 8,900‑square‑foot house in 1987 with his then‑wife Kelly Rector; the two sold it off‑market in 2021 for about $85 million, according to ELLE Decor. The property was originally purchased from the family of Juan Trippe, former president of Pan American World Airways, and later renovated by renowned architect Thierry Despont.
The main residence, designed by Joseph Greenleaf Thorp in the 1890s, blends Shingle Style details—beamed ceilings, wide‑plank floors, crown molding—with modern upgrades like a mirrored catwalk and a two‑story fireplace. The current owner installed impact‑resistant windows, smart‑home systems, and energy‑efficient HVAC, preserving historic character while meeting contemporary luxury standards.
The property’s 500‑foot stretch of ocean frontage and a private boathouse on Georgica Pond give it resort‑like appeal; a red‑clay tennis court and expansive entertaining spaces add to its allure. The land can be split into two parcels, each with its own building rights, offering investors flexibility for additional residences.
With the listing price approaching the record, elite buyers are lining up; a closing is anticipated within the next three months, and the estate is expected to be sold before the end of 2024.