Calvin Klein’s former Hamptons estate is back in the spotlight. This time, it could make real estate history. The sprawling oceanfront property in East Hampton has hit the market for a staggering $165 million, a price that would set a new record for the most expensive home ever sold in the Hamptons if a buyer steps forward. This new listing comes just five years after the fashion icon sold the estate for $85 million, which just highlights the huge growth of the region’s ultra-luxury market.
Most Expensive Hamptons Home?
This East Hampton mansion has been listed for $165 million. It was sold by Klein for $85 million in 2021, according to the Daily Mail.
This could be a record sale for the area. The most expensive home ever sold in the Hamptons to date is an East Hampton home that was purchased by hedge-funder titan Barry Rosentein. He bought the home for $137 million in 2014.
We have seen some deals come close to breaking the record, including the $118.5 million sale of an oceanfront Walter Mill home by apparel executives Arthur Rabin and Jason Rabin in 2021.
There is another listing trying to break that record. An oceanfront Sagaponack compound is currently listed for $152.5 million.
Details on the Home
If the Calvin Klein home sells, then the new owners would purchase a luxurious main residence that was originally built for attorney Henry A. James and his New York socialite wife, Laura Brevoort Sedgwick James, in the 1890s.
Juan Trippe, founder of Pan American World Airways, was the next owner. He reportedly used a seaplane to reach the property before he sold it to Klein in the 1980s.
The home features picturesque views of the Atlantic Ocean and Georgica Pond. It has seven bedrooms and spans 9,000 square feet and features gambrel roofs.
There is a tower with a domed ceiling. This happens to contain a bedroom and a family room with a wet bar. The listing also states the current owner did a “major renovation,” which preserved the historic details like the original wide-plank pine flooring.
Price Is Justified
Ed Petrie of Compass is marketing the property. He said the asking price is justified because of the $85 million purchase price in 2021, in addition to the cost of renovations completed. Add in the property’s rare 1.89-acre oceanfront lot, which happens to allow for a second buildable home.
Petrie told the Daily Mail, “We generally don’t get properties with this type of acreage and an additional buildable oceanfront lot. That’s part of the reason for the price tag.”
They also added that a 2,150-square-foot guesthouse could be built on the property.
Record Hampton Sales
We have seen a surge in Hampton home prices in recent months. They are reaching record highs amid a broader market rebound. The median luxury home price rose 30% in the first quarter of 2026.
While overall home sales have been showing signs of cooling off, the ultra-luxury market in the Hamptons continues to defy the broader slowdown. These high-end deals, especially deals above $10 million, are being driven largely by cash buyers and scarce inventory.
