Long Island’s Most Expensive 2021 Home Sales by the Numbers

Montauk Lighthouse Long Island, New York


Long Island real estate had an unforgettable and, in many ways, unfathomable year in 2021. Historic highs in demand compared with noteworthy lows in inventory and number of days properties remained on the market, infinite stories about baffling bidding wars, open house lines winding around blocks, and of course, those seemingly ever-upward prices in many markets, particularly on the high end.

Among the many lofty sales in 2021, somebody had to come out on top. Drumroll, please, as we explore the top 10 most expensive sales of the year by the numbers…

  • $634.5 million: Total cost of top 10 Long Island home sales in 2021, the highest such total in history
  • $457.7 million: Total cost of top 10 Long Island home sales in 2020
  • $105,000,000: Sale price of 90 Jule Pond Drive in Water Mill, the priciest Long Island home sale of 2021—and the highest ever paid for a solo piece of property on Long Island’s famed East End. In 2014
  • 75: The street address and number in millions for the second most expensive deal of the year—for Calvin Klein’s former digs on West End Road in East Hampton
  • 66: The street number and the number in millions for the fourth most expensive home sale of the year, on Wainscott Main Street in Wainscott.
  • 10: Number of homes in the top 10 that are located in the Hamptons. Yes, that means they were all located in the Hamptons.
  • 7: Number of Long Island homes that sold for more than $50 million, more than in any other single year
  • 1: Home in the top 10 that is noton the ocean—38 Mathews Lane in Wainscott, which sold for $47 million
  • 0: Homes in Sagaponack—home to ZIP code 11962, which in November was named the third most expensive ZIP code in America, and the highest in New York—that made the year’s Top 10