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.