The 10 Most Expensive Hamptons Real Estate Deals of 2021 – DIRT


What a year! To be fair, 2021 was an incredible year for real estate in general, with records being broken all over the place, from Palm Beach, Miami, and Montana, where Rupert Murdoch dropped $200 million on a ranch, to Vancouver, Dubai, and the Cayman Islands. Not too surprisingly, the Hamptons also came on strong, with the top 10 deals totaling a whopping $607 million, about 35 percent more than 2020’s list.

In Southampton, the highest price ever paid for a single parcel was achieved in 2021, with the $105 million sale of the former Ford estate. (Some may remember that in 2014, hedgie Barry Rosenstein paid $137 million paid for an estate on Further Lane, but that property was in three parcels.) The enormous, 42-acre oceanfront property, once known as Fordune but now known as Jule Pond, had languished on the market for four years, initially at $175 million but with a last asking price of $145 million.

Another market laggard also finally traded in 2021: Burnt Point, in Wainscott, sold for $47 million, just about half of the $95 million pharma billionaire Stewart Rahr initially asked when it was listed back in 2015.

A number of this year’s top deals were done off market. Calvin Klein astonished the world by selling an oceanfront estate in a clandestine off-market deal for $85 million, a price that puts it at number two on our list. The 10-acre spread had long been occupied by Klein’s ex-wife Kelly Klein. Real estate watchers will recall that in 2020, Klein’s sale of his contemporary house on Southampton’s Meadow Lane, for approximately $85 million to trophy property collecting hedge funder Ken Griffin, was the number one sale in the Hamptons. (Calvin — any other $85 million properties we don’t know about? Call us.)

Speaking of Meadow Lane, often called Billionaires’ Lane, for the 1% of the 1% who own homes along the slender beachfront road, the Southampton street usually dominates the Hamptons top ten lists, but this year Meadow Lane had just two entries on the list, adding up to $113 million. Meanwhile, perennial bridesmaid Further Lane, in East Hampton, which is also ridiculously ritzy but sometimes a shade less expensive than Meadow Lane, had a great year, with three entries on the list adding up to $174 million. We’ve included Spaeth Lane, which is one of the tiny oceanfront lanes that lead off Further Lane, but even if we left it off, Further Lane would squeak past Meadow with $114 million in sales. There’s always next year, Meadow Lane.

Now, to the list!



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