Est. worth: $10 million 

Twitter's co-funder managed to score the 3,7000-square-foot house for nearly half the original market value ($18 million), making it the most expensive two-bedroom house in San Francisco at the time. Dorsey's setup consists of a 20-foot retractable glass roof that doubles as a sky light, plus custom Brazilian-wood cabinetry and stunning views of the Golden Gate Bridge. #Swanky!