The 21 Most Expensive Hamptons Home Sales of 2021

Jule Pond, a massive 42-acre estate with three waterfront sides, sold earlier this year for a whopping $105 million.
Courtesy Bespoke Real Estate

This past year has been another banner year in Hamptons real estate during the COVID-19 pandemic when wealthy New Yorkers continued to see value in private spaces near some of the most beautiful beaches in the world.

During 2021, we saw some mega deals close, such as the largest sale in Hamptons history and the big- gest price paid for non-ocean waterfront. Behind The Hedges combed through data available for 2021 and confirmed known sales as of December 26 with various brokerages putting the deals together.

Jule Pond was once the center of the massive Ford estate.Courtesy of Bespoke Real Estate

1) Jule Pond, Water Mill | $105 million

Topping the list is the record-breaking sale in Water Mill, which not only is the biggest of the year, but in Hamptons history. Jule Pond, a 42-acre waterfront estate with unobstructed views of the Atlantic Ocean and Mecox Bay, sold in August.

The closing price makes the Jule Pond transaction the most expensive sale for a single piece of property ever on the East End. In 2014, hedge fund manager Barry Rosenstein famously paid $147 million for his Further Lane estate in East Hampton, but that was the total price for three separate, yet contiguous parcels. The biggest of the properties, 62 Further Lane, traded at just $97 million, leaving room for the Jule Pond transaction to steal the record.

Bespoke Real Estate in Water Mill and Ellen Stern at Julia B. Fee Sotheby’s International Realty in Rye had the co-exclusive on 90 Jule Pond Drive, but we’re told Bespoke largely handled the transaction. When it went into contract in April, June Pond was asking $145 million. It first went on the market for $175 million in 2017.

For a bit of comparison, the biggest sale in 2020 was billionaire Ken Griffin’s home on Meadow Lane in Southampton, which sold for $84.4 million.

2) 75 + 69 West End Road, East Hampton Village | $85 million

Back in May, Calvin Klein quietly sold an oceanfront estate he has long owned for a combined $85 million. The 6.8-acre parcel with the residence at 75 West End Road sold for $75 million while the vacant adjacent 1.63-acre property went for $10 million. Neither was publically listed for sale at the time and the same buyer appears to have snatched up both properties. Matt Breitenbach and John Gicking, both of Compass, represented the buyer.

The nearly 20,000-square-foot estate at 840 Meadow Lane sold for $70 million. Tim Davis declined to identify the buyer, but said plans call for a major renovation that could cost north of $25 million.

3) 840 Meadow Lane, Southampton Village | $70 million

A 19,000-square-foot, 30-room fairytale Tudor mansion, originally built in 1929 as a summer cottage sold in November. Tim Davis of the Corcoran Group represented the oceanfront property that went on the market in June for $75 million. The 8.3-acre property also boasts a 48-foot swimming pool with a spa and a tennis court, as well as a bayfront parcel with a boat mooring.

4) 66 Main Street, Wainscott | $66 million

Thirty-one acres on the east side of Wainscott Pond sold in April in an off-market deal put together by Ed Petrie of Compass. While the property came with a 19th-century carriage house, the value was in the land, which had long been in David Osborn’s family. The buyer was listed as a limited liability company.

The home at 30 Spaeth Lane in East Hampton Village Courtesy of Brown Harris Stevens

5) 30 Spaeth Lane, East Hampton Village | $60 million

Back in the first quarter, some of the highest-priced Hamptons homes sold — and two of them are neighboring properties off of East Hampton’s famed Further Lane. The property at 30 Spaeth Lane sold for $60 million on March 15. While the 7.7-acre property with a six-bedroom, five-bathroom house was originally listed for $72 million, the last asking price was $67 million. Peter Turino and Christopher Burnside of Brown Harris Stevens represented the sellers in the off-market deal and Frank Newbold of Sotheby’s brought the buyer.

The home at 70 Further Lane closed at $59.5 million Courtesy of Brown Harris Stevens

6) 70 Further Lane, East Hampton Village | $59.5 million

Located next to 30 Spaeth Lane, 70 Further Lane also sold in an off-market deal on February 5. The home belonged to billionaire investor James Chanos, the founder of Kynikos Associates, a firm specializing in short selling, perhaps best known for predicting the collapse of Enron. (In fact, he’s called the “LeBron James of short selling.”) Hedgerow Exclusive Properties brought the buyer, while Brown Harris Stevens’ Peter Turino and Shannon North repped the seller.

The East Hampton home at 442 Further LaneCourtesy of Hedgerow Exclusive Properties

7) 442 Further Lane, Amagansett | $55 million

The four-acre oceanfront property on East Hampton’s famed Further Lane sold for $2.5 million above the asking price in early December. Listed with Hedgerow Exclusive Properties, it went into contract in less than 30 days. Catherine Juracich of Douglas Elliman brought the buyer, who the New York Post reported as Peloton CEO John Foley, for the 6,100-square-foot home designed by the late architect Francis Fleetwood.

The last asking price on Stewart Rahr’s estate, Burnt Point, was $56 million.Courtesy of Bespoke Real Estate

8) 38 Mathews Lane, Wainscott | $47 million

Burnt Point, a 25,000-square-foot home set on 25 secluded acres on Georgica Pond, sold in April. Billionaire former pharmaceuticals entrepreneur Stewart Rahr had been asking $56 million. Bespoke Real Estate, which also represented the listing, says it was the highest price for a non-ocean waterfront.

Barnes Coy Architects designed the modern home at 115 Beach Lane.Paul Domzal | Chris Foster | BarnesCoy | MayfairConstruction

9) 115 Beach Lane, Wainscott | $45 million

The contemporary 11,000-square-foot home, designed by Barnes Coy Architects, recently appeared in an episode of HBO’s Succession, before it sold in late November. Bespoke represented both sides in the transaction. The 2.55-acre property, framed by 230 feet of oceanfront and farm fields, first went on the market in 2020 for $52 million.

10) 40 Meadow Lane, Southampton Village | $43 million

New England Patriots owner Robert Kraft bought the oceanfront house in an off-market trade brokered by Hedgerow Exclusive Properties, as well as Douglas Elliman, in April. The exact sale price for the home on Billionaires’ Row was $42,923,600. It is by far the smallest piece of land on our list at 0.76 of an acre, while the modern home is 6,600 square feet.

11) 260 + 264 Jobs Lane, Bridgehampton |$38 million

Two lots on Mecox Bay were sold to the same buyer in a quiet off-market trade that closed in late September. Hedgerow represented both sides.

12) 9 Olde Towne Lane, Southampton Village | $34.6 million

Little is known about the transaction for this gated estate on four manicured acres in the exclusive Olde Towne enclave. Developed by John Kean, the 15,500-square-foot home offers state-of-the-art amenities and interiors by the noted designer Anthony Ingrao. There’s a 6,000-square-foot lower level with a theater, gym, two-lane bowling alley, wine cellar and more, a roof deck provides ocean views and a putting green, plus there’s a pool, an oversized spa and an outdoor kitchen. The home closed on April 20 for $34,638,000.

13) 249 Surfside Drive, Bridgehampton | $32 million

Million Dollar Listing’s Ryan Serhant quietly closed on this off-market deal in mid-December. Serhant, who runs an eponymous brokerage based in New York City, represented both sides. His representatives declined to comment. Of note, this wasn’t Serhant’s largest deal on that block; he also sold 263 Surfside Drive for $40 million in 2019.

SandcastleCourtesy Farrell Building

14) 612 Halsey Lane, Bridgehampton | $31 million

Hamptons powerhouse builder Joe Farrell finally sold his home, dubbed Sandcastle, in November. An 11.5-acre estate, once rented by Jay-Z and Beyoncé, it features every conceivable luxurious amenity inside the 9,000-square-foot abode and out. Since Farrell completed the home 12 years ago, it has been on and off the market, once for as much as $60 million. The last ask in the open listing was $34.995 million and Tal Alexander and Sara Goldfarb of Douglas Elliman Real Estate brought the buyers and closed the deal.

The oceanfront home at 38 Association Road sold in late DecemberCourtesy of Bespoke Real Estate

15) 38 Association Road, Wainscott | $30 million

Bespoke represented the seller of this oceanfront 6,537-square-foot abode. Michelle Tiberio and Andy Volet of The Corcoran Group represented the buyer. The transaction closed in late December with a last ask of $37 million. In Wainscott, there are just seven oceanfront properties and Bespoke has sold four of them since 2020, 18 oceanfront homes overall in that time frame.

16) 1360 Meadow Lane, Southampton | $28.5 million

Situated on a private oceanfront lot, the 2.5-acre lot has 125 feet of oceanfront. It sold in April in a deal done directly with the buyer.

Courtesy of Sotheby’s International Realty

17) 67 Surfside Drive, Bridgehampton | $28.5 million

An oceanfront property made out to be Gordon Gekko’s house in the 1987 film Wall Street sold in May. The final figure was high, by all accounts, given the main home only has four bedrooms (five in to- tal with one above the garage). Hedgerow Exclusive Properties brought the buyer. The 2.2-acre property was listed with Beatte V. Moore of Sotheby’s International Realty since late 2018.

18) 569 Ox Pasture Road, Southampton Village | $28.45 million

A 9,500-square-foot Georgian house set on a 4.6- acre parcel on Handy Creek, just moments to Coopers Beach, was sold in July. The property has 357 feet of waterfront with a private dock, a pool with a pool house and the stately main home with nine bedrooms, seven full baths and two half baths. Erica Grossman of Douglas Elliman represented the listing, which had a last ask of $32 million.

The oceanfront home at 1750 Meadow LaneCourtesy Corcoran

19) 1750 Meadow Lane, Southampton | $28.32 million

This 4-acre property offers stunning views of both the ocean and Shinnecock Bay and boasts 200 feet of ocean frontage. The 6,000-square-foot modern home was listed with Corcoran’s Tim Davis. The property also features a pool, tennis court and private boardwalk to the ocean.

The bayfront property at 258 Horsemill Lane in Water Mill Courtesy of Corcoran

20) 258 Horsemill Lane, Water Mill |$28 million

Chris Burch, a venture capitalist who helped launch his then-wife’s eponymous fashion brand, Tory Burch, was the reported buyer of a 6.9-acre spread on Mecox Bay in June. Listowel, as the estate is called, is surrounded on three sides by farmland, in addition to 360 feet of bayfront. The 12,000-square-foot shingle-style home sits amid a classic English garden. It was listed with Corcoran’s Tim Davis and Douglas Elliman Real Estate’s Erica Grossman for $29.5 million.

The 2.6-acre property at 159 Trees Lane, including ocean frontage, sold for $26 million in January.Taylor K. Vecsey

21) 159 Trees Lane, Sagaponack | $26 million

Billionaire businessman Peter Brant and his wife, supermodel Stephanie Seymour, sold their ocean-front home at the top of the year for $26 million and it remained the biggest trade in Sagaponack this year. Records show the house was built in 1994 and measures a mere 2,668 square feet (small for a Sagaponack home on the ocean) with four bedrooms and five baths. The couple bought the 2.6-acre lot in 2002 for $6.1 million. We’re told Hedgerow represented them in the off-market deal and Beate V. Moore of Sotheby’s brought the buyer.

Honorable Mentions:

The home at 25 Quimby Lane sold for $25 million.Richard Taverna for Sotheby’s International Realty

22) 25 Quimby Lane, Bridgehampton | $25 million

A home with 18th-century roots that underwent an impressive renovation in recent years got a new owner on August 31, just five months after it came on the market. The initial ask: $28.5 million. Frank Newbold and Beate V. Moore of Sotheby’s International Realty represented sellers Chris Mitchell, the former publisher of Vanity Fair, and Pilar Guzmán, former editor in chief of Condé Nast Traveler and co-founder of social platform The Swell. They bought the home in 2019 for $7.1 million, records show. Bayard Fenwick of the Terry Cohen Team at Saunders & Associates brought the buyer.

This article has been updated since it appeared in Dan’s Papers. Behind The Hedges will continue to update this list online as we discover any other sales have closed before the New Year. 

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