Daniel Milstein for Sotheby’s International Realty
Don’t let these blockbuster numbers fool you. While 2023’s 10 priciest real estate transactions racked up a total sales volume of nearly $1.2 billion, slightly surpassing our 2022 list’s tally, these deals were the exceptions. In almost every luxury market across the country, overall volume declined by double-digit percentages compared to the prior year, driven by economic jitters and soaring interest rates. Among the most severely impacted markets was the greater Los Angeles area, where there’s currently a glut of luxury mansions up for grabs, many of them sporting heavily slashed listing prices. Even typically downturn-proof communities such as Aspen and Palm Beach were not immune to the slowdown.
As always, a majority of the top 10 deals were hush-hush transfers inked off-market. And it’s worth noting that all but two of the deals involved oceanfront—or at least waterfront—properties, suggesting buyers are still willing to shell out big for trophy vacation homes with direct beach access. Here’s our list of 2023’s priciest residential sales.
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1. Paradise Cove, Malibu—$190 million
Image Credit: Google Earth Coming in at the top of the heap, and the only California property to make the list, was this colossal blufftop complex atop Paradise Cove in Malibu, which sold for $190 million in cash. This year’s biggest real estate transfer was also likely the most highly publicized, thanks to A-list buyers Jay-Z and Beyonce. It’s the priciest-ever deal for a California home, and the second-priciest ever recorded nationwide.
First commissioned in the late 1990s by Bill and Maria Bell—he the son of the soap opera tycoons who created The Young and the Restless and The Bold and the Beautiful—the house took 15 years to plan and build. Completed circa 2014, the monolithic fortress was created, at least partially, to display the Bells’ enormous collection of modern art, including numerous works by Jeff Koons, Andy Warhol, Damien Hirst and Marcel Duchamp. Though the property was never publicly marketed for sale, the Bells had reportedly shopped the place off-market with a whopping $250 million ask.
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2. North County Road, Palm Beach—$170 million
Image Credit: Google Earth In April, New York-based car dealership mogul Michael Cantanucci broke the Palm Beach record with his $170 million purchase of this oceanfront estate, which features a nearly 25,000-square-foot, Tuscan-style mansion built in the 2000s. The house was never on the market, so further details are scant, but the seller was billionaire coffee entrepreneur Bob Stiller, who paid just $25 million for the estate in 2014.
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3. North Ocean Boulevard, Palm Beach—$155 million
Image Credit: Google Earth Although it was quickly overshadowed by the Stiller-Cantanucci deal, the $155 million sale of the late Rush Limbaugh’s Palm Beach estate certainly made headlines when it closed in March. Once again, the property was never openly listed for sale, but tax records show the multi-structure compound was built in the early 1990s and sits on 2.2 acres of oceanfront land, with a very impressive 250-feet of beach frontage. The buyer, cosmetics heir William Lauder, also owns lavish homes in Beverly Hills and New York.
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4. Copper Beech Farm, Greenwich—$138.8 million
Image Credit: Daniel Milstein for Sotheby’s International Realty This year’s most out-of-left-field big transfer was likely the sale of Connecticut’s Copper Beech Farm, which recorded at a state record of nearly $140 million. The deal came even as the Greenwich real estate market has badly sagged in recent years. The seller, billionaire Ray Dalio, had paid $120 million for the place back in 2014, though that unconventional transaction reportedly included the assumption of tens of millions worth of debt on the estate. The all-cash buyer, who remains anonymous for now, is thought to hail from Mainland China. Copper Beech Farm features 50-acres of land with a 13,500-square-foot main house originally built in 1898, plus spectacular gardens and roughly a mile of private water frontage on Long Island Sound.
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5. Meadow Lane, Southampton—$112.5 million
Image Credit: Google Earth New York’s biggest deal of 2023 was inked in the Hamptons, and it’s no surprise that the property in question is one of the largest estates on Southampton’s ultra-prime Meadow Lane—often called Billionaires’ Row. The titanic spread sold for $112.5 million to an as-yet-unidentified billionaire shielded behind a Delaware entity called Meerkat LLC, with the thrifty buyer negotiating a cool 36% discount off the estate’s $175 million original ask. Long owned by ad exec Marcia Riklis, the so-called Mylestone estate is anchored by an 18,000-square-foot manor house situated on 8-acres of land, with nearly 500 feet of ocean frontage.
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6. Windmill Lane, East Hampton—$91.5 million
Image Credit: Google Earth Talk about a profitable flip. The seller of this two-parcel East Hampton compound, real estate investor Peter Fine, bought the property in 2020 for $45 million. Just three years later, without making any significant changes to the place, he flipped it for an eye-popping $91.5 million to an unidentified buyer. Still not crazy enough for you? There are rumors the new owner might tear down the estate’s current structures to build something more lavish, so that $91.5 million might’ve been for the land alone.
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7. Great Island, Darien, Connecticut—$85 million
Image Credit: Google Earth Great Island, a 63-acre waterfront property on Long Island Sound, features a land bridge that connects to the mainland in Darien, Conn. For decades, the island served as the ultimate private compound since it was built at the turn of the century, with amenities such as world-class equestrian facilities (including a polo practice field), a private beach, and a secluded harbor with a dock and boat house. Owned for over 100 years by different generations of the same family and originally offered at $175 million, the giant estate was acquired by the town of Darien for a heavily discounted $85 million. At last check, the town was still deciding what to do with the island, which features a 13,000-square-foot historic mansion and multiple ancillary structures.
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8. 220 Central Park South, New York City—$80 million
Image Credit: Google Earth The two-building skyscraper at 220 Central Park South is famously a huge hit with billionaires, so it’s no surprise that New York City’s biggest residential deal of 2023 was recorded at the limestone complex. This time, it was a duplex penthouse at the shorter “villa” building that fetched $80 million in a staggering resale. While the unit itself was never on the market, sellers Suna Said and her husband Scott Maslin had paid about $66 million for the Central Park-facing apartment in 2020. The anonymous buyer, who may or may not be a big-name celebrity, has a Los Angeles mailing address.
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9. Indian Creek Island, Miami—$79 million
Image Credit: Google Earth In October, two months after paying $68 million for an oceanfront estate on Miami’s Indian Creek island, Jeff Bezos dropped $79 million on the house next door. The lucky neighbor, who acquired the 19,000-square-foot mansion back in 2014 for just $28 million, remains unknown. Bezos reportedly plans to bulldoze both properties to make way for a custom compound of his own creation, so that $79 million was likely just for the dirt alone.
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10. Ute Avenue, Aspen—$76 million
Image Credit: Google Earth Aspen’s biggest-ever home sale was unconventional in more ways than one. Unlike most of the other properties on this list, the $76 million deal was not an all-cash transfer. The buyer, car dealership mogul Terry Taylor, paid $51 million of the purchase price in cash but also gave the seller, real estate developer Leathem Stern, a smaller Aspen home valued at $25 million. The ski-in, ski-out house features four full floors totaling more than 20,000 square feet of living space. Not everyone who crossed paths with the property enjoyed the experience, however—a Christie’s real estate agent is currently suing Stern for $1.7 million in commission payments she claims were owed to her in the deal.
