On February 8, 2010, it was reported that O'Brien was attempting to sell his Central Park West penthouse in New York with an asking price of $35 million. He had purchased the apartment in 2007 for $10 million. Two years earlier, O'Brien had purchased a home in the Brentwood section of Los Angeles for over $10.5 million. Some industry insiders have speculated that O'Brien had chosen to stay on the west coast in order to facilitate a return to late night television and because he did not want to put his children through another move.