Even before buying Lanai, the sixth-largest of the Hawaiian Islands, Larry Ellison was spending money like few other CEOs in America.

In the mid-2000s Ellison, the founder of the computer behemoth Oracle, commissioned what was then the biggest yacht in the world, the 452-foot Rising Sun, at a reported cost of $270 million dollars. (He later sold it and has since bought another, smaller yacht at around 250-feet).

He’s owned multiple planes, including a Gulfstream that served as the design inspiration for Steve Jobs’s plane.

An avid tennis fan, he bought the Indian Wells tennis tournament for a reported $100 million in 2009.

He reportedly spent $100 million or more on his America’s Cup sailing race win in 2010.

His biggest spending, however, is real estate. Noone knows exactly how many properties Ellison owns, but publicly available records show that at one time, he owned the following:

Malibu, CA – Five adjacent lots on Carbon Beach.

San Francisco – A 10,742-foot home in Pacific Heights, which was at the center a tree dispute.

Woodside, CA – Two properties, including a 23-acre property modeled on a Japanese emperor’s palace.

Newort, RI – A mansion formerly owned by the Astor family

Koyto, Japan – An historic garden property

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