The Bellwether Listings

Proper Upper East Side brokers are a calm crowd. With nice posture and even tones, they’ll tell you that luxury New York real estate is doing just fine, even if there’s fiery chaos outside. But this autumn there may be reason to actually share in their confidence.

If a few elephantine, long-simmering, high-profile properties can manage to sell at half-reasonable prices this fall, when activity tends to pick up, they’ll have an outsize effect on the city’s roughed-up ego.

To be sure, the only thing that will really rekindle those bubbly realty glory days is hordes of absurdly wealthy people spending absurd sums of money again. If that actually happens, it won’t be for a while. “Time is the new four-letter word,” the appraiser Jonathan Miller said Monday.

But it wasn’t long ago that the luxury real estate market looked a lot worse. “There was no market,” Stribling Private Brokerage director Kirk Henckels said about this winter. Phones started to ring again in the spring, but “it was a totally socially unacceptable time to purchase, given the amount of damage that was being done. And people don’t bid in a market when they don’t know what the market is.”

This summer, while most New Yorkers were away licking wounds, Madonna paid $32 million for a 12,000-square-foot mansion, even though its location was slightly bizarre. Last week, a deed surfaced in city records showing that Lehman villain Dick Fuld sold his apartment for $25.87 million. “Look, how long was that on the market, a week? And that sold for a very strong price,” Mr. Henckels said. “The rest of his investments should have done so well.”

After Labor Day, top brokers’ shiny eyes will be trained on 10 or so big listings: Call them the bellwethers. It’s not that a few mammoth deals can heroically save all of rich New York’s real estate: But if Mrs. Astor’s 778 Park Avenue duplex finally sells after three cuts and two brokers, the whole block will look better; if Julian Schnabel can unload his half-price duplex or triplex at the Palazzo Chupi, the Village’s weirdest real estate chapter can close; if the Plaza sells off its disgraced penthouse or third-floor maze, those Eloise jokes stop.

“We’re all watching carefully,” Brown Harris Stevens director John Burger said. “The patient has resuscitated.” - By Max Abelson

This year, only nine months after it was bought for a boroughwide record $7 million, a penthouse loft in the Clock Tower Building was listed for $8.5 million; then news came that the triplex upstairs was being listed for $25 million. Luxury Brooklyn real estate won’t look so terribly, massively passé if both can somehow sell.

Angel Franco/New York Times.

The old hotel’s $60 million, 9,799- square-foot penthouse is the most expensive apartment available in New York City—and its $35,445 monthly maintenance fee doesn’t help matters. But its living room alone is 47 feet wide and 26 feet tall. “I think it’s pretty remarkable,” Mr. Henckels said. “I’m not sure who the buyer is for that; I’m not sure it’s American. I think, probably, a foreign buyer.”

Corcoran.

When the Web site ScoutingNY compared Julian Schnabel’s off-pink Palazzo Chupi to Disney World’s Tower of Terror this July, it was only an architectural jab. But the West Village condo’s fall has been petrifying: The asking price for its triplex and duplex has fallen from $59 million to $27.9 million. If either gets sold off, the entire neighborhood will look a lot shinier again.

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There are five apartments asking more than $10 million at the prim East River co-op, which is a bothersome glut. Even if snobs snicker at the entire Sutton Place neighborhood (too far from Fifth Avenue!), the River House has come close to big sales: Earlier this year, a buyer went to contract on producer Marty Richards’ $22.7 million maisonette, which has been off and on the market the entire decade. The deal fell through.

cityrealty.com.

It was three years ago this October that the mastermind financier J. Christopher Flowers bought Harkness for $53 million, still the largest sum ever spent on a New York townhouse. This February, The Observer reported that the 113-year-old, 50-foot-wide mansion was quietly available for $49.95 million because of his divorce. Although it still needs to be renovated, the tag is relatively modest—especially considering that millions have been spent on a gut job.

The odd thing about super-expensive townhouses like Madonna’s is that they often need a lot of work, or they’re in slightly odd locales. But this 30-foot-wide house, a fashion executive’s, is on a gallingly perfect block, and was entirely rebuilt after a three-alarm fire in 2006. This March, The Observer reported that it was quietly available for $52 million with Paula Del Nunzio. “If she ends up getting $45 million,” another top broker offered, “then that means one of the 25-footers that are done could really be in the high $20s, if not in the $30s.”

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The year has not been kind to this hotel–turned–mega condo, which managed to become a black sheep even though the seventh-floor sprawl that Harry Macklowe bought up is still the city’s priciest stretch of residential real estate. But if developer El-Ad can resell either the triplex penthouse that oligarch Andrei Vavilov left behind after a lawsuit, or the $45 million third-floor sprawl that businessman Luigi Zunino has apparently abandoned, its reputation will change. (And don’t forget the two apartments that owners are trying to flip for $38 million each.)

There was a demented moment when four units on three consecutive floors were available at the beloved and hilariously tough 2 East 67th—a $117 million, 17-bedroom fantasy triplex. Even though the east half of the fourth floor is now off the market, the others are still on for a total of $103 million. What the building needs is one plush sale to make the block feel dictatorial again.

“To be retrospective about anything is being retrospective,” the scandalized, sad-eyed Anthony D. Marshall told The Observer last year. Back then, the 778 Park duplex that belonged to his mother, Brooke Astor, was on the market for $46 million. Since then its price has sunk to $24.9 million. If this can’t sell (and remember that the $24.5 million listing for William F. Buckley’s duplex downstairs was taken off the market), is there any hope for anyone?

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In 2006, Sting listed his 6,600- square-foot duplex apartment with the star broker Linda Stein—who was killed a year later, allegedly by an assistant. His price has since hopped from $26 million to $19 million, and where he sells will give Central Park West a good sense of its new-era worth. “It’s kind of anyone’s guess,” Mr. Henckels said.

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