Standing on the sun-drenched rooftop of what might be the largest private residence in Jerusalem, Tomer Dowek described how a mansion in the capital’s central Rehavia neighborhood became part of Israel’s cultural history. “When industrialist Miles Sherover opened this home in 1956, it was the largest private residence in Israel, and became a center for hosting heads of state, international dignitaries, and the elites of Israeli society,” explained Dowek, vice president of business development at Prosperity Real Estate, the agency managing the estate’s sale. “There are no private estates of this scale available today.” The property, popularly known as Villa...