Castillo Del Lago - Leon Max's House (Formerly Madonna's and Bugsy Siegel's)

Castillo Del Lago is a historic estate in Hollywood Hills which was built in 1926 by John De Lario for oil explorer Patrick Longdon and it is widely believed to have been home to mobster Bugsy Siegel who reportedly used the house as an illegal speakeasy and gambling parlor, natch. In the 1950s, the property fell into a state of disrepair and transferred hands several times until 1993 when it was purchased by pop icon Madonna for $5 Million.

Soon after buying Castillo del Lago, Madonna had it painted in bright red and yellow horizontal stripes and the original roof tiles were replaced with new ones. This mortified her neighbours, in particular architecture writer, real estate king and next door neighbour Crosby Doe. In a 2004 Times Online article he is quoted saying: “She wrecked it. They took the historic tiles off the roof, threw them in a dumpster and put on these Taco Bell tiles. It was one desecration after another.”. Christopher Ciccone, Madonna’s brother and former interior designer, says the stripes were inspired by a church in Portofino, Italy. Madonna reportedly spent around $500.000 on renovations.

Madonna sold Castillo Del Lago just three years later in 1996 after her security guards shot a stalker who tried to break into the house through a window.

Madonna sold Castillo Del Lago for $5 Million without making any profit on the sale. It was sold to commercial director Joe Pytka, who put it on the market in 2009 for $15 Million. It was then sold to it's current owner, fashion designer Leon Max for $7 Million in 2010. Max put the house on the market in February 2023 for $21 Million.