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The 10 most expensive homes sold on Long Island in 2021

Seven Long Island homes sold for more than $50 million in 2021, a record for the region’s highest end properties, and a sign of changing attitudes about the value of ultra-luxury real estate.

The most expensive among the seven was the $105 million sale of 90 Jule Pond Drive in Water Mill in August. Those seven sales compared with three deals greater than $50 million in 2020. Before that, there hadn’t been a sale that reached that threshold since 2016, according to an analysis by appraisal firm Miller Samuel for Newsday.

The top 10 sales on the Island all cleared $40 million and all were in the Hamptons — in East Hampton, Southampton, Wainscott and Water Mill.

The flashy sales are part of a global trend in the ultra-luxury market, said Jonathan Miller, CEO of Miller Samuel. He counted 41 home sales of more than $50 million in the United States last year, an increase of 41.4% compared with 2020. One caveat: Off-market transcations, which aren't disclosed on Multiple Listing Services, can be hard to track if they aren't widely publicized.

Miller said persistently low interest rates have driven up asset prices, creating some of the wealth required to make these purchases. He cautioned that this top tier of sales has less to do with any broad price appreciation in Hamptons real estate than a global reset in the prices attached to trophy properties.

"It’s not as if giant homes on Long Island are now being constructed and they’re selling for uber prices," Miller said. "The perceived valuation of these properties has been reset to a much higher level, and that has much less to do with the local housing market than it does national and global factors."

Some of the factors that contributed to the larger number of high-end sales last year include the wealth created in the financial markets during the pandemic, and the success of Wall Street firms during that time, which has enriched the financiers that have historically bought these homes, Miller said. Some wealthy individuals opt to buy hard assets instead of financial instruments as part of their investment strategies, he said.

"One of the reasons why 2021 was a banner year for the East End is that Wall Street had an amazing year, and Wall Street is joined at the hip with the East End," Miller said.

Joseph De Sane, a broker and managing director at Bespoke Real Estate in Water Mill, which marketed the Jule Pond property, said the pandemic led more people to consider the Hamptons as a year-round home from which they could work. Early on in the pandemic, buyers placed a premium on homes that included amenities, such as gyms and home theaters that were ready for use, but as time went on more buyers were willing to purchase properties needing renovations. He has seen an expansion in the areas where homes can sell for top prices. More homes north of Montauk Highway — farther from the ocean — are selling for $10 million or more than in the past, he said.

"I do think you’ll start to see people look to areas that are just north instead of the typical old ‘south of the highway near the ocean.’" De Sane said. "As price points increase, the barrier to entry increases, and they’ll need to be open to other areas."

Todd Bourgard, who oversees Douglas Elliman Real Estate’s eight offices in the Hamptons, said he has been pleasantly surprised that the luxury market has persisted through the pandemic. He said, as of late December, Douglas Elliman's Hamptons offices were involved in a record $3.2 billion worth of deals last year, compared with $2.9 billion in 2020.

"We’d sometimes see these homes sit six months to a year. Now, if they’re priced properly, within two weeks, we are looking at several offers," Bourgard said. "With the terms people are coming in with — cash, no contingencies — they’re closing up quicker than ever also."

Below are the top 10 sales last year on Long Island. The list includes sales reported by Miller Samuel as well as information from real estate brokerages and media reports.

$105 million: 90 Jule Pond Dr., Water Mill

The 42-acre property has nearly a quarter-mile of ocean frontage. It was built in 1957 as part of the estate of Henry Ford II, grandson of the founder of Ford Motor Co. The house has 12 bedrooms, 12 full bathrooms and 20,000 square feet of living space. It was the highest price paid for a single parcel of land in Hamptons history. Billionaire Barry Rosenstein’s 2014 purchase of an East Hampton home for $147 million that included multiple parcels still holds the record for the highest East End home sale.

The Jule Pond estate had previously sold for $22 million in 2002. Bespoke Real Estate and Ellen Stern of William Pitt and Julia B. Fee Sotheby’s International Realty co-listed the property. Bespoke Real Estate represented the buyer and seller in the transaction.

$85 million: 75 West End Rd., East Hampton

Calvin Klein sold this two-parcel property in East Hampton to a single buyer who used LLCs to make the purchase, according to Behind the Hedges, which reports on East End real estate. The estate covers nearly 8.5 acres and features a 10,176-square-foot home.

$70 million; 840 Meadow Ln., Southampton

This 30-room Tudor mansion was sold in November by an LLC associated with the late Julia Vance Carter, an attorney, The Wall Street Journal reported. The 8.3-acre property has about 500 feet of ocean frontage and a home that is nearly 20,000 square feet. Tim Davis of the Corcoran Group represented the seller.

$66 million: 66 Wainscott Main St., Wainscott

This property covers about 31 acres near Wainscott Pond. The modest house on the property was a four-bedroom, one-bathroom barn, according to a real estate listing. Zoning rules in the Town of East Hampton could allow for six homes to be built on the land, according to

$60 million: 30 Spaeth Ln., East Hampton

This secluded mid-century modern house sits on 7.7 acres and has more than 300 feet of ocean frontage. The 15,421-square-foot house has six bedrooms, five full bathrooms, and a second-floor porch with ocean views, according to the listing. The seller was the estate of the late June Noble Smith Larkin Gibson, the daughter of Edward J. Noble, who founded the Life Savers and Candy Co. and American Broadcasting Co., according to Peter Turino and Christopher Burnside at Brown Harris Stevens represented the seller.

$59.5 million: 70 Further Ln., East Hampton

A short walk from 30 Spaeth is 70 Further Lane, which sold in an off-market deal in February, transferring the home from one owner shielded by an LLC to another. The seller was billionaire investment manager Jim Chanos, Behind the Hedges reported. Peter Turino and Shannan North at Brown Harris Stevens represented the seller.

$55 million: 442 Further Ln., East Hampton

This four-acre property sold quickly in December for $2.5 million above asking price. The 6,100-square-foot home has 400 feet of ocean frontage and five bedrooms. The home has multiple second floor sundecks, and its four second-floor bedrooms have ocean views, according to the listing. The seller was the estate of Alan Seligson, the former chairman of a company that made parts for the aerospace industry, who died last year, the New York Post reported. The listing brokerage was Hedgerow Exclusive Properties. Catherine Juracich at Douglas Elliman Real Estate represented the buyer.

$47 million: 38 Mathews Rd., Wainscott

Located on about 25 acres on Georgica Pond, this 18,000-square-foot property is known as Burnt Point. The eight-bedroom estate is filled with luxury amenities, including a beamed library, paneled office, professional screening room and wine cellar, according to a listing. The home has about 2,000 feet of waterfront on the pond but is not directly on the ocean. It had sold for a then-record price, at $45 million, in 2005. The seller was the Stewart J. Rahr Foundation, the charity founded by pharmaceutical executive Stewart J. Rahr, reported.

$45 million: 115 Beach Ln., Wainscott

This home, built in 2018, sits on more than 2.5 acres and has six bedrooms and 10 full bathrooms. The 11,000-square-foot property has gigantic windows with ocean views, 230 feet of oceanfront and an attached four-car garage, according to a video from Bespoke Real Estate, which represented the buyer and seller. The home was featured in an episode during the third season of "Succession" on HBO, according to Curbed.

$42,923,600: 40 Meadow Ln., Southampton

This beachfront, seven-bedroom home, built in 2017, sits on three-quarters of an acre. Brokers at Hedgerow Exclusive Properties and Douglas Elliman were involved in the sale.

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