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.