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A History of the Biggest Whale Flops In New York City

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New York City has plenty of mindbogglingly priced apartments?we're all very familiar with the $100 million City Spire penthouse and $95 million Sherry Netherland apartment?but sometimes these places just aren't worth as much as the seller seems to think. While the aforementioned have yet to meet the PriceChopper, plenty of stunning homes?like William F. Buckley's Park Avenue maisonette and the Gwathmey-designed police building?have been hacked to pieces over the years. For this special Whale Week feature, we revisited the properties of the Pricechopper Hall of Fame to look at the city's biggest whale flops, and we did a little fortune-telling, predicting some future contestants.

Where: 240 Centre Street, #5H
Original ask: $30 million
Sold for: Trick question! It never sold. $14.5 million was the final listing price.
The skinny: The saddest of whale flops, this place had all the makings for a perfect whale story: the ex-COO of an investment bank, pre-crash buy, post-crash listing, and a famous architect-designed apartment. We're talking, of course, about the bonkers Charles Gwathmey-designed apartment in the old gymnasium of the former police building at 240 Centre Street. The sprawling 6,600-square-foot apartment has a room that is 60-feet long, 40-feet wide, and 25-feet high. Yeah. Ex-Bear Stearns COO Alvin Einbender bought the place some years ago for $2.2 million, then paid $13.3 million to have his buddy Gwathmey make it over. Einbender first listed it for $30 million just two months after Bear Stearns' collapse in 2008, and the first price decrease came a year later, when it dipped $4 million lower. Then things . Between 2009 and 2011, the place saw four big pricechops, with a final June 2011 asking price of $14.5 million?52 percent less than the original ask. What makes it even sadder, though, is that it seems like the place never sold. In February of last year, it was transferred to a trust in Einbender's name. Maybe one day we will witness its triumphant return.

Where: 812 Park Avenue, PHA
Original ask: $36.5 million in 2007
Sold for: $15.9 million in 2011
The Skinny: For 25 years, financier Gordon Pattee and his wife called this penthouse home, and they renovated it sometime in the early 2000s, restoring J.E.R. Carpenter's original prewar details. They first listed it at a whopping pre-crash $36.5 million in November 2007. It saw its first pricechop about a year later, dipping to $29.75 million. A few more months pass, the economy is still crap, and it has another several million chopped off, landing at $22 million. Then it took a three-month hiatus. After three years and no buyer, had the Pattees given up? Not quite. It returned to the market in September 2010, with a final asking price of $15.9 million?more than 56 percent less than the original asking price. In April 2011, it sold for that price to Edgar Bronfman, who is a true NYC real estate whale?he has bought and sold more than $150 million in properties over the past decade. Clearly, he knew a good Park Avenue deal when he saw one.

Where: 43 Wooster Street, PHE
Original ask: $12.5 million in November 2007
Sold for: $3.995 million in July 2011
The Skinny: The pricechoppage did not come slowly for this penthouse. It was originally listed, pre-crash, for $12.5 million, which works out to more than $4,700/square foot. A year after it was first listed, it lopped off more than 50 percent of its price over a two-week period that saw five pricechops, landing at the ask of $5.9 million in November 2008. Over the next three years, it saw several more chops, and finally sold in 2011 for $3.995 million. The seller likely lost out on a few hundred thousand, possibly even a million, as it was purchased in 2006 for $4.171 million, then renovated. Plus all of the furniture came with the place. Whatever went wrong with that renovation should be a lesson in how NOT to flip an apartment.

Where: 630 Park Avenue, penthouse
Original ask: $17 million in September 2006
Sold for: $7.616 million in March 2011
The skinny: This Whale Flop could have been a sadder story, but the sale price was actually 17.2 percent more than the final asking price of $6.5 million. The place was originally designed (in 1916) as a 4BR/5BA megaspread, but when it hit the market in 2006 for $17 million, it was described as a "raw space." The listing photos showed lots of concrete and white walls. It disappeared after the market collapsed, and came back in 2009 first for $12.5M, then $8.5M, then finally, in 2010, $6.5M. The buyers were the uber rich couple William and Katherine Birch, who no doubt have been enjoying the pad's wraparound terrace. They are probably not enjoying the $7,287 monthly maintenance.

Where: 778 Park Avenue, Maisonette
Original ask: $24.5 million in May 2008
Sold for: $8.75 million in January 2011
The skinny: This sale made headlines not only for its massive pricechoppage, but also for the famous names. The sellers was the estate of magazine publisher and conservative thinker William F. Buckley, and the buyers were Mark and Renee Rockefeller (yes, of course those Rockefellers). The final asking price for the duplex maisonette was $10 million in December 2010, but it sold for 12.5 percent less than that. The total choppage? A whopping 64.3 percent. Yikes. The Buckleys had decorated the 5,000-square-foot place with lots of red, gold, heavy curtains, and marble, so we'd love to see what the Rockefellers have done with the place.

Whale Flops of the Future?

Where: 105 Eighth Avenue, Brooklyn
The skinny: Brooklyn's most expensive house, a former Montessori school, has been on the market for a few months, and has already had its pricechopped from $25 million to $18 million.

Where: Azure at 333 East 91st Street
The skinny: Furniture dealer Larry Gaslow is trying for a $3 million profit on his 2,952-square-foot apartment at the Azure, where he probably has never lived. It seems that he spent the whole year renovating the place, turning a 4BR/4.5BA into a 2BR/2.5BA.

Where: The Royal York, 425 East 63rd Street
The skinny: The sellers of this penthouse aren't even trying. It has been on the market since 2007! And it won't submit to the pricechopper. The ask has only gone from $5.9 to $5.699 million. Perhaps if they got rid of the creepy ventriloquist dolls they'd have better luck.

Where: 910A in 1 Beekman Place
The skinny: More than four years on the market, and the price for this 3BR/3.5BA has gone from $13.9M to $10.5M. But it probably won't sell anytime soon because the maintenance/CC fees are a mindboggling $18,318/month.
· Whale Week coverage [Curbed]

778 Park Avenue

778 Park Avenue, New York, NY 10021

240 Centre St

240 Centre Street, Manhattan, NY 10012

812 Park Avenue

812 Park Avenue, New York, NY 10021