Last week, we featured properties in New York City that were sold for only one dollar. This week, we’re looking at the flip side: some of the most expensive real estate deals that have taken place in New York City. This goes beyond the $100+ million dollar apartment listings you’re familiar with – these deals give you a sense of not only the size of transactions here in the city but the scale of the urban development that emerge from them.

All of these deals were over $1 billion, and included both single buildings and large complexes. We’ve come a long way from the “Million Dollar Corner,” on 34th Street and Broadway, which in 1911 was the most ever paid for a plot of land. In 2015 dollars, that sale for the 1,200 square foot corner would have been equivalent to $25.7 million.

1. Stuyvesant Town-Peter Cooper Village: $5.45 Billion

-Peter Cooper Village covers 80 acres of Manhattan, making it New York City’s largest apartment complex. The urban renewal parcel was built with a priority to returning veterans from World War II, with support from none other than Robert Moses.

In 2015, Stuyvesant Town and Peter Cooper Village were sold to Blackstone Group by CWCapital Asset Management, which represented the bondholders on the property. In 2006, BlackRock Realty Advisors and Tischman Speyer bought the properties for $5.4 billion but had lost it by 2009 when Tischman Speyer defaulted on the mortgage. When the 2015 deal was completed, it was the largest real estate transaction ever to take place in New York City.

2. General Motors Building $2.8 Billion

The General Motors Building at 767 Fifth Avenue (where the Fifth Avenue Apple store cube is) has had numerous record breaking deals. The building is located between 58th and 58th Streets next to Central Park, with notable nearby buildings including the Plaza Hotel, the Sherry-Netherland Hotel, and Bergdorf Goodman.

In 1998, Donald Trump and Concesco, a financial services company, bought the building for $178 million and sold it in 2003 for $1.4 billion to the New York City-real estate company, the Macklowe Organization. Then in 2008, Macklowe sold it for $2.8 billion to a joint venture between Goldman Sachs Real Estate Opportunities Fund, Boston Properties, and Dubai-based Meraas Capital. It was the largest-single building transaction in 2008 and would not be rivaled until 2015. It has a current estimated value of $3.4 billion.

3. 11 Madison Avenue: $2.29 Billion

Located next to Madison Square Park, another one of New York City’s iconic parks, the Art Deco 11 Madison Avenue was sold for $2.29 billion in 2015, making it the second highest sale price for an office building in the United States. Whereas the General Motors Building was purchased via a joint venture between three companies, 11 Madison Avenue was bought by one company: SL Green Realty Corp., of the largest real estate companies in New YOrk City.

The landmarked building, designed by Harvey Wiley Corbett and Dan Everett Waid, was built as part of the Metropolitan Life company complex, along with the recognizable clocktower at 1 Madison Avenue. Both buildings are connected via a skybridge. 11 Madison Avenue was originally planned to be 100 stories, which would have been the tallest in the world. The completed structure, which would have been the base of the building, has the foundational support to reach 100 stories. Today, 11 Madison Avenue houses the headquarters of Credit Suisse, Sony Corporation, the restaurant 11 Madison Park, and other businesses.

4. Google Headquarters: 111 8th Avenue $1.8 Billion

In 2010, Google purchased 111 8th Avenue for $1.8 billion. The large building, which encompasses an entire city block between 15th and 16th Street, and 8th and 9th Avenue, was originally constructed in 1932 as the Port Authority Commerce Building/Union Inland Terminal. Later, it served as the headquarters for the Port Authority until the agency relocated to the original World Trade Center in 1970.

Initially, goods were moved by truck from this building to railroad and shipping lines, with the upper floors constructed as manufacturing space. As a warehouse, it did not have to subscribe to the zoning laws of the time period and avoided having to be “set back,” like other buildings. As a result, there is more square footage in 111 8th Avenue than there is in the Empire State Building. Today, there are numerous tenants inside the building besides Google, which has been unable to end the leases of some companies that were already in the building. As a result, Google still rents office space in other buildings in the city, including above Chelsea Market.

5. Rockefeller Center: $1.85 Billion

Rockefeller Center, previously owned by the Mitsubishi Estate and other owners, was purchased by Jerry Speyer of Tishman Speyer and the Lester Crown Family in 2001 for $1.85 billion, a deal which included both the buildings and the land. The new owners immediately sold off a portion of 30 Rockefeller Center (see below) and worked on making the struggling Rockefeller Center profitable again.

6. 666 Fifth Avenue $1.8 Billion

Lobby of 666 Fifth Avenue with art by Isamu Noguchi

In 2007, 666 Fifth Avenue was the most expensive ever paid for a single office building in the United States. Kushner Properties was the buyer, a family-owned real estate company, and this was one of its first major forays into the Manhattan real estate market. The New York Times wrote that the purchase was “considered a classic example of reckless underwriting,” reflecting the height of real estate transactions just before the last recession, but also notes the clever restructuring and deals that have taken place since then to keep the building in play. Today, most know this building because of the the Uniqlo store on the ground floors, designed by architect Masamichi Katayama and his firm Wonderwall. It is also home to the Hollister store, Zara and Tissot. Inside, there is an Isamu Noguchi installation in the lobby.

7. One Worldwide Plaza $1.7 Billion

Architecture buffs are likely familiar with Worldwide Plaza, designed by David Childs of Skidmore, Owings and Merrill with a large plaza between the three buildings of the complex.  Transit riders will know it because it’s also the entrance to 50th Street A/C/E stop, which includes the fun city-oriented window artwork. But from the skyline, it may be the pyramidal topped building in Midtown you always wondered about.

One Worldwide Plaza sold for $1.7 billion in 2007 to Deutche Bank, but just two years later it was sold again at just $600 million. Today, the building is home to CBS.

8. 30 Rockefeller Center $1.3 Billion

In 2013, Comcast purchased a 49% stake in NBCUniversal from General Electric. Part of the $16.7 billion deal included 1.3 million square feet inside 30 Rockefeller Center and other properties in New Jersey for a $1.4 billion price tag. As a reference, General Electric paid $440 million for this space in 1996. The building also contains the famed NBC Studios and the Top of the Rock.

9. 650 Madison Avenue $1.3 Billion

Located just next to the General Motors Building and behind the Sherry-Netherland Hotel, 650 Madison Avenue was sold in 2013 for $1.3 billion by Carlyle Group LP to Crown Acquisitions Inc. and Highgate Holdings. From the ground level, shoppers will know this building to be the home of Crate & Barrel, Polo Ralph Laure and other luxury retail, which helped drive up the price of the deal. Above, the building contains office space. At the time, it was the largest deal in the United States since the Google acquisition of 111 8th Avenue. Carlyle and Crown also bought controlling states in the retail portion of 666 Fifth Avenue (earlier on this list) in 2013.

10. 550 Madison Avenue, Sony Tower $1.1 Billion

550 Madison Avenue with its “Chippendale” cutout on top

The Sony Tower was built by architect Philip Johnson and John Burgee and is notable for its “Chippendale” cutout roof. At the bottom, there is a privately owned public space and a SONY technology lab. In 2013, the building was sold to the Chetrit Group for $1.1 billion, a price Bloomberg Technology called “aggressive.” The Sony headquarters were to stay in the building until 2016, whereupon it will move to 11 Madison Avenue (also on this list). The top floors were to be converted into luxury condos designed by Robert A.M. Stern but as with a forthcoming sale of the building for $1.3 – $1.4 billion, it looks like the condo plans will be dropped.

11. 399 Park Avenue $1.06 Billion

Rendering for updated 399 Park Avenue by Gensler

399 Park Avenue, also known as the Citigroup Building, was sold in 2002 for $1.06 billion. Citigroup was one of the first to move uptown in the mid-20th century and its move back downtown had put Park Avenue landlords “on edge,” as reported by the Wall Street Journal. In 2002, it was the most expensive price paid for an office building in America. Earlier this year, major upgrades were announced for 399 Park Avenue including an outdoor elevated green space, a facade reclad from limestone to metal, and street level improvements. The redesign is being handled by the architecture firm, Gensler.

Bonus: Hudson Yards and Deals to Come

Worthy of mention as well is the $1 billion lease of air rights at Hudson Yards to Tishman Speyer from the MTA for 99 years. In the large-scale potential deals to come in 2016, there is the the sale of the Plaza Hotel for a potential $1 billion, the potential Citigroup buy back of its Tribeca headquarters at 388-390 Greenwich Street for $2 billion, and many more.

Next, check out the flip side: 10 properties in NYC sold for $1.