Designed by Robert Finkelhor and updated in the 1950s by John Elgin Woolf, Bob Hope's long-time manor on four parcels of land in Toluca Lake is a timeless classic, much like the man himself. Hope and his wife Dolores moved to the property in 1939, then kept acquiring more and more of the surrounding land, putting down gardens and adding greens and two pools (one indoor, one outdoor). The walled and gated eight-bedroom estate, today nearly 15,000 square feet, was definitely made for entertaining, with its enormous family room, sprawling patio, and one-hole, three-par golf course. The property was listed for the first time ever in 2013, asking $27.5 million; it was eventually pricechopped down to $21.8 million. After some time off the market, it's back and now asking $23 million.