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Five of the Upper East Side's Most Absurd, Obstinate Listings

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Welcome back to Chopper Holdouts, a feature where we delve into the world of listings that time forgot. Whether it's ego, stubbornness, or desperate hope, these places have been on the market for years without chopping their prices significantly. Any suggestions? Send them to the tipline.

There are few places on earth that mix ridiculously extravagant real estate with massive egos as potently as the Upper East Side. The result of that mixture: a whole bunch of enormous penthouses and townhouses, lingering on the market year after year without ever admitting that they might be overreaching a little with their asking prices. Places like the Woolworth Mansion (pictured), or the townhouse 53 East 64th Street, which, in its three years on the market, has managed to increase its price from $15.7 million to $26 million. Because what did you expect it to do, ask for less money? Discounting is gauche.


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1. 53 East 64th Street

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53 East 64th Street
New York, NY 10065

This 7,000-square-foot, six-story Lenox Hill townhouse is just a classic Chopper Holdout. In September of 2010, it was listed for $15,700,000. Two years passed and no buyer emerged, so what did the the owner do? He raised the price to $18 million. Two weeks ago, he raised it again, to $26 million. This guy doesn't take any crap, least of all from the housing market. Want to buy this house next year? That'll be ten billion dollars. Deal with it.

2. 106 East 71st Street

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106 East 71st Street
New York, NY 10021

Three years on the market has been enough for onetime flip attempt 106 East 71st Street to back off ever so slightly from its original ask. The 10,000-square-foot limestone mansion now costs $26.5 million, down from $28.8 million. That should do it.

3. 30 East 85th Street #8DEF

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30 East 85th Street
New York, NY 10028

Another of the inexplicable PriceUppers, this three-unit combo was first listed for $6.995 million in 2010, chopped down to $5.995 million later that year, and has been climbing ever since. It's now at $7.9 million.

4. 304 East 65th Street #37

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304 East 65th Street
New York, NY 10065

The listing for this glassy penthouse in The Rio has committed the classic staging faux pas of photographing the bathtub with water in it. How does this even happen? No one knows. Out of all the places on this map, though, this one appears to be the most willing to negotiate, having chopped its price three times since it was listed for $12 million in 2010. It's down to $9.5 million now, but the last chop was over a year ago.

5. Woolworth Mansion

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4 East 80th Street
New York, NY 10075

The Woolworth Mansion is the undisputed king of Chopper Holdouts, and mansions, and everything. The 20,000-square-foot townhouse has been on the market for $90 million since early 2011. It had a short-lived foray as a $210,000/month rental, later reduced to $165,000, but never once cut its sale price. And why should it? If ever there was a place that deserved to hold out, this is it.

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1. 53 East 64th Street

53 East 64th Street, New York, NY 10065

This 7,000-square-foot, six-story Lenox Hill townhouse is just a classic Chopper Holdout. In September of 2010, it was listed for $15,700,000. Two years passed and no buyer emerged, so what did the the owner do? He raised the price to $18 million. Two weeks ago, he raised it again, to $26 million. This guy doesn't take any crap, least of all from the housing market. Want to buy this house next year? That'll be ten billion dollars. Deal with it.

53 East 64th Street
New York, NY 10065

2. 106 East 71st Street

106 East 71st Street, New York, NY 10021

Three years on the market has been enough for onetime flip attempt 106 East 71st Street to back off ever so slightly from its original ask. The 10,000-square-foot limestone mansion now costs $26.5 million, down from $28.8 million. That should do it.

106 East 71st Street
New York, NY 10021

3. 30 East 85th Street #8DEF

30 East 85th Street, New York, NY 10028

Another of the inexplicable PriceUppers, this three-unit combo was first listed for $6.995 million in 2010, chopped down to $5.995 million later that year, and has been climbing ever since. It's now at $7.9 million.

30 East 85th Street
New York, NY 10028

4. 304 East 65th Street #37

304 East 65th Street, New York, NY 10065

The listing for this glassy penthouse in The Rio has committed the classic staging faux pas of photographing the bathtub with water in it. How does this even happen? No one knows. Out of all the places on this map, though, this one appears to be the most willing to negotiate, having chopped its price three times since it was listed for $12 million in 2010. It's down to $9.5 million now, but the last chop was over a year ago.

304 East 65th Street
New York, NY 10065

5. Woolworth Mansion

4 East 80th Street, New York, NY 10075

The Woolworth Mansion is the undisputed king of Chopper Holdouts, and mansions, and everything. The 20,000-square-foot townhouse has been on the market for $90 million since early 2011. It had a short-lived foray as a $210,000/month rental, later reduced to $165,000, but never once cut its sale price. And why should it? If ever there was a place that deserved to hold out, this is it.

4 East 80th Street
New York, NY 10075