2. General Motors Building
Sale price: $2.9 billion
Size: 2 million square feet
Location: New York, N.Y.
New York City real estate mogul Harry Macklowe proved that in the world of commercial real estate, there can be too much of a good thing. In 2007, he scooped up seven Manhattan office buildings from private equity giant Blackstone Group, with the hopes of dramatically expanding the size of his real estate empire.However, the loans used to make those purchases became nearly impossible to refinance once credit markets started to freeze up shortly thereafter. As a result, Macklowe's firm was forced to sell off some of those properties, including what perhaps was his most prized trophy: the General Motors building, a 50-story white marble landmark with breathtaking views of New York City's Central Park and home to iconic toymaker FAO Schwarz as well as Apple's flagship Fifth Avenue store. At least it wasn't all for naught -- Macklowe more than doubled his investment on the building after purchasing it for $1.4 billion in 2003.
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