It was the deal that would underscore both the highs and the lows of the Manhattan real estate market. When insurance giant MetLife (NASDAQ:MET - News) put the 11,000-unit apartment complex on the block in 2006, it became one of the most coveted commercial properties, sparking a fierce bidding war.

In the span of a little more than three years however, Stuyvesant Town/Peter Cooper Village quickly morphed from the proverbial brass ring into a white elephant as its buyers choked on the massive amount of debt used to finance the purchase. The owners - Tishman Speyer Properties and BlackRock Realty -- handed over the property to its creditors in January.

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 (NASDAQ:GM - News) building, a 50-story white marble landmark with breathtaking views of New York City's Central Park and home to iconic toymaker FAO Schwartz as well as Apple's (NASDAQ:AAPL - News) 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.

It wasn't swashbuckling pirates that ultimately brought Las Vegas icon Treasure Island to its knees. Rather, last year's distressed sale of the casino and its accompanying 2,885-room hotel was a necessary sacrifice for its former owner MGM Mirage.

Struggling with a difficult economic climate and hoping to raise some quick cash for its ambitious cross-town City Center venture, the casino operator sold the resort and its famous pirate battle display last March for a mere $775 million. Scooped up by Kansas billionaire Phil Ruffin, various estimates have placed the site's replacement value at nearly four times that amount at $2.7 billion, according to commercial real estate research firm CoStar Group.

Boston's John Hancock Tower might just represent everything that went wrong with the broader U.S. commercial real estate market. Relying on massive amounts of financing, an ambitious New York City-based investment firm scooped up New England's tallest office building in 2006 for an eye-popping $1.3 billion, betting that Boston's office rental market and commercial property values would continue to remain red hot.

What they never anticipated, like so many other real-estate speculators, was the precipitous decline in property values and a spike in the nation's unemployment rate to above 10%, which drastically weakened demand for office space across the country. Unable to service the debt load, the property was sold in a foreclosure auction last March for less than half of the original purchase price.

When the Hancock Tower stumbled, so did Universal City Plaza. Sold together as part of a portfolio of foreclosed holdings last March, the property became one of the more high-profile casualties of the Southern California commercial real estate market since the start of the recession.

Home to a number of media and entertainment companies, including NBC Universal and Universal Music, the 36-story building and surrounding land is now jointly owned by a pair of East Coast distressed investment firms.

In the world of commercial real estate, history does sometimes have a habit of repeating itself. For years, the Carillon Hotel was a fixture of the Miami Beach scene, only to be shuttered in the late 1980s as a result of a tough economic climate.

After a massive overhaul, the property reopened in 2008 as a hotel-condominium combination under the banner of Canyon Ranch, a well-respected name within the wellness community. That venture however would stumble yet again as a result of the recent economic downturn. Last fall, its developers handed over the remaining 300-plus unsold condos to its creditors.

Despite that hiccup, the Canyon Ranch development appears to be moving full steam ahead. More than 60 units have been sold since May and another 20 contracts are waiting to be completed, according to its current owners.