Take, for example, the ten-room spread on the fourth-floor of the Dakota—one of the most legendary co-ops in New York (where else can one mingle at an annual October potluck with both Lauren Bacall and Yoko Ono?)—that has been on the market since October 2006.
The $14.5 million apartment lacks park views, and its décor is a bit theatrical, but it has 4,500 square feet, six fireplaces, and a shaving closet. Still, after so many years, even the Warburg listing sounds fatigued, sapped of the energy to string clauses and descriptions into proper sentences; it ends with a semi-coherent fade out: “One of a kind. Function and glamour………….As fabulous as your fantasy.”
A few dozen blocks north, on Central Park West, the turreted, red-brick condo conversion at 455 CPW has had a terrible time trying to lure buyers. The former nursing home and New York Cancer Hospital has undergone an impressive makeover, but No. LM17 and LM19 both hit the market in December 2006, where they remain to this day, asking $5.6 million and $3.8 million respectively. Manhattanville isn’t the most prestigious address, and buyers may have an aversion to moving into a building where most residents once left in body bags. But can that really explain a half-decade of snubbing?
And what of the penthouse at 425 East 63rd Street, listed since February 2007? Doesn’t anyone want a $5.6 million penthouse on Lexington and 63rd Street, even if it does look like something out of a Jackie Collins novel? The long-suffering broker, Debra Forest of AIB Management Corp., admitted there were a few things that might not appeal to potential buyers: the penthouse is actually two separate units that would need to be combined, and the décor is “circa the 1980s.” But she remains confident someone will be thrilled to snap it up. “I’m definitely not worried,” she said. “The owner is not worried.”
There might be any number of deficiencies or problems with apartments that linger, according to Jonathan Miller of appraisal firm Miller Samuel, but the only real problem is price. “There’s always a price to match a buyer,” he said. “Even when someone is murdered in an apartment, there’s a price it will sell for.”
What’s more, overpricing can backfire. A study Mr. Miller did with the Furman Center at NYU found that the closer the seller lists a property to its actual market value, the higher the price it actually sells for. And conversely, he said, “if you throw a property on for an absurdly high price, you end up getting less than you would have if you had listed it close to market value.”
Vanity and ego are the two major driving factors behind many outrageous asking prices. Take, for example, the townhouse at 22 East 71st Street, purchased by Aby Rosen for $15.6 million in 2004. After completing a partial renovation, the real estate tycoon relisted it for a whopping $75 million in 2008, making it the most expensive townhouse listing at the time, (that honor now belongs to the $90 million Woolworth Mansion). Mr. Rosen, who never lived in the home, eventually dropped the ask to $50 million in 2011 and the property is now said to be in contract to the Qatari prime minister for $47 million.
“Aby is Aby,” said one high-end broker. “It’s ego.”
Nobody who has had their property on the market for more than three years really wants to sell, claimed Fred Peters, the president of Warburg Realty. Some sellers are parading a trophy, some are testing the market and some are simply delusional. But, said Mr. Peters, “at some point, the pain becomes too much. It all depends on where the threshold is.”
At this point, the seller frequently moves on to a second broker (indeed, most lingering listings leave a string of jilted brokers in their wake), for whom he or she is often willing to lower the price. The Chelsea penthouse, for example, burned through nine different brokers and four different brokerages. And that’s not even counting the rental brokers.
Other reasons that places sit: a fussy co-op board kills a low offer, or it’s an estate, notoriously difficult to sell because the apartments often need renovation and bickering heirs are reluctant to lower prices. But most brokers blame dust-covered listings on unrealistic sellers and the brokers who are only too happy to tell them what they wanted to hear in exchange for a wildly expensive exclusive listing and the publicity that comes with it.

129 W. 20th: “But in real estate, your dream penthouse is not someone else’s dream penthouse.”
I’m not sure anyone’s dream penthouse would have the guest powder room — the only bathroom on the entertainment floor — located directly from middle of the dining room. Why wouldn’t an owner/developer realize that before dropping so much money into the unit?