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The 20 Biggest Residential Deals of the Decade

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Our end-of-decade examination series kicked off with a countdown of the best new buildings in New York City. Oh, building boom, you were so kind. And speaking of booms, it's now time for a look at the biggest deals of the '00s. Of course the biggest deal of the decade?and any decade, for that matter?was the $5.4 billion purchase of the 11,000+ apartments of Stuyvesant Town and Peter Cooper Village. Buyer's remorse, perhaps? We're more interested in the individual, single-family stuff?folks hashing it out over four walls, a roof and a toilet. Or in these cases, 20 rooms, private roof decks and his-and-her bidets. These are, to the best of our hard-working interns' knowledge, the biggest sales in an era fueled by excess. Flips of trophy properties were common. Records were set and immediately shattered. That's all gone, for now, but the memory lives in on this document. Got proof of a bigger deal we missed? The tipline is always open.

20) $34,000,000
Building: 777 Washington Street
Buyer: Noam Gottesman
The Skinny: Big-time hedge-funder (get used to seeing those on this list) paid this crazy amount for photographer Albert Watson's 20,000-square-foot West Village studio and townhouse, then promptly tore the whole thing down.

19) $35,000,000
Building: 36 East 75th Street
Buyer: Russian Federation
The Skinny: This 25-foot-wide Georgian mansion now belongs to Russia, which chose it over the more-popular-in-the-fatherland Vision Mashine for its new UN consulate.

18) $36,630,000
Building: 720 Park Avenue
Buyer: Peter and Jill Kraus
The Skinny: Though the deed was only in Jill Kraus's name, odds are the cash for this classic co-op came from Peter, a former Merrill Lynch executive who received a $25 million bonus after working at the firm for just three months. The purchase price was nearly twice what the previous owner paid two years before.

17) $37,000,000
Building: 15 Central Park West
Buyer: Novgorod & Novgorod Two LLC
The Skinny: 15 CPW's first spot on the list goes to this penthouse, picked up by a mysterious buyer with Russian overtones. It sold post-Lehman, in September 2009, which is quite the achievement. But the penthouse, originally purchased for $21.5 million by a London-based investor, was listed as high as $80 million.

16) $37,000,000
Building: Time Warner Center
Buyer: Andrei Vavilov
The Skinny: Another post-Lehman surprise, the south tower penthouse was bought by the mysterious Russian oligarch and Plaza plaintiff. Vavilov snapped this baby up at a hefty discount from its original ask of $65 million.

15) $37,500,000
Building: 810 Fifth Avenue
Buyer: Peter G. Peterson
The Skinny: Seller David Geffen flipped this penthouse co-op apartment to a former Secretary of Commerce for a (comparatively) slim profit. He paid $31.5 million for it in 2006.

14) $40,000,000
Building: 1009 Fifth Avenue
Buyer: Tamir Sapir
The Skinny: The Duke Semans mansion, all seven floors and 20,000 sq. ft. of it, was originally listed at $50,000,000 but was snatched up for less by taxi driver turned oil billionaire turned real estate magnate Tamir Sapir. The building was the subject of much celebrity speculation (Martha Stewart, Lenny Kravitz), but never count out an old cabbie.

13) $42,250,000
Building: Time Warner Center
Buyer: David Martinez
The Skinny: Mexican moneybags David Martinez picked up his first TWC condo in 2003 for this amount, but later added another 4,200 square feet for millions more, giving him the full 76th and 77th floors in one of the towers.

12) $42,405,000
Building: 15 Central Park West
Buyer: Sanford Weill
The Skinny: Former Citigroup CEO Sandy Weill nabbed the building's largest terrace in this buy. Gives him some good 15 CPW bragging rights, but not the building's biggest buy.

11) $44,000,000
Building: 834 Fifth Avenue
Buyer: Rupert Murdoch
The Skinny: Ditching Soho, which never fit him anyway, Murdoch laid out a record amount (at the time, anyway) for the triplex penthouse in this traditional power building. He then gave the neighborhood an eyeful while renovating.

10) $45,000,000
Building: 15 Central Park West
Buyer: Daniel S. Loeb
The Skinny: Though he shelled out more for his "Tower" penthouse than Sandy Weill did on his "House" side penthouse (and briefly set a Manhattan record), hedge-fund king Loeb paid far less per square foot ($4,200 to Weiss's $6,200). Bargain!

9) $45,100,956
Building: The Plaza
Buyer: Kayhil Holdings
The Skinny: What is Kayhil Holdings? No clue, but it shelled out the cash outright for an 11,861-square-foot spread on the 11th floor of the Plaza. Five months later, amid the mortgage meltdown, Chase wrote a $20 million mortgage for the unit.

8) $46,000,000
Building: 1060 Fifth Avenue
Buyer: Scott Bommer
The Skinny: What made this record (at the time) purchase for a co-op so amazing was that the duplex was still technically two separate apartments. Hedgie Bommer then convinced the board to let him combine the floors into one penthouse. Yep, it was a $46 million fixer-upper. But Bommer didn't stick around for long.

7) $46,320,395
Building: 14-16 East 67th Street
Buyer: Laurus Funds
The Skinny: We know the double-wide Milbank Mansion as the "Guccione Mansion," because the Penthouse founder added Caligula-like touches to this limestone palace such as Roman statues around an indoor pool over his 30 years in the place. This deal was actually a transfer between creditors after Guccione lost the mansion.

6) $48,000,000
Building: 2 East 67th Street
Buyer: Jonathan Tisch
The Skinny: After selling a Fifth Avenue duplex to Starbucks CEO Howard Schulz, the billionaire Loews heir and chairman paid 20% above the asking price for the 11th floor of this historic, Oliver Stone-approved co-op.

5) $48,836,000
Building 1060 Fifth Avenue
Buyer: Park View Trust
The Skinny: Deciding maybe he didn't want to get into a renovation after all, Scott Bommer turned around and flipped his two separate floors for a co-op record price that still stands today. The buyer remained anonymous.

4) $49,000,000
Building: 14-16 East 67th Street
Buyer: Philip Falcone
The Skinny: The creditors that took over the Guccione Mansion put it on the market for $59 million and hoped for a townhouse record, but they fell short. Hedge-fund manager Falcone got the porn king's sloppy seconds despite already owning a townhouse on the block.

3) $50,000,000
Building: 15 East 64th Street
Buyer: Len Blavatnik
The Skinny: What's $50 million between friends? The wily Russian bought this townhouse from his buddy, Seagram heir and music executive Edgar Bronfman, Jr., even though Bronfman paid just $4.375 million for the place in the '90s. Hopefully the house is holding up better than his fortune.

2) $52,032,554
Building: The Plaza
Buyer: Harry Macklowe
The Skinny: Though it was rumored he was spending $60 million to combine most of the seventh floor of the landmark hotel, to the best of our knowledge developer Macklowe shelled out a bit less on seven apartments on the same June 2007 day (he was one of the first to close in the building). And so began his troubles.

1) $53,000,000
Building: 4 East 75th Street
Buyer: J. Christopher Flowers
The Skinny: The Harkness Mansion once held the record for the city's priciest sale after trading hands for $6.9 million in 1987. How times have changed! Investor Flowers was the first to break the $50 million mark when he picked up the 50-foot-wide house at the height of the market back in 2006. It had been listed for $55 million, and word was it sold for $46 million. Nah-ah. It was destined for greatness!
· Top of the Aughts [Curbed]