The 28 of '08

What a year, eh? Arab money, Irish money, federal money, no money! This year was the annum when the party stopped and the hangover started, and New Yorkers slept little in between. Both the residential and commercial real estate markets stormed into Jan. 1 of this year happy and bloated, wafted along by hefty credit markets, an indifferent government and a can-do fervor.

And why not? Last year had marked record amounts of investment and apartment and building sales. And the possibilities appeared endless, as lenders poured capital in and buyers yanked it out to satiate markets where $5,000 for a square foot of condo space or $1 billion for an office building felt normal and never-ending.

So long to all that.

As 2008 closes, certain properties stand emblematic of the year’s triumphs and tribulations. Below comes a ranking of the 28 most representative—the towers, sites, stores, developments and complexes that captured a New York City in transition from thrill to chill, and that show the direction of the city property-wise in 2009 and beyond.

A couple of things about the list. One, it’s not all gloom and doom. Some properties made it because they succeeded, either by dumb luck, superior quality or savvy marketing (or a combination of the trio). Two, the properties that come in for critique suffer often because of circumstances: It was a bad year all around.

Just ask 383 Madison, which made the list at No. 8. It was Bear Stearns’ world headquarters.