“When you start getting north of $10 million, it’s a lot of that stuff never goes to market, a lot of pocket listings or quiet listings,” says DeSimone. “They’re only sold through brokers you know.” 

The Simple Life

While many of the country’s most expensive homes are in high-end hot spots, Los Olivos is not an obvious place to invest in luxury real estate. It’s not that the town is just sleepy—it’s totally zonked. In a good way. For those who like that sort of thing.

“People who come here are looking for a place in a rural community where they can have peace and quiet and relax,” says Natale. “They’re not into the cocktail parties every Friday night.” He calls it a Levis and t-shirts kind of place, for people who love horses or vineyards, but not the limelight.

“When Michael Jackson was up here, he didn’t go around the community much,” says Natale. “He had his own environment, his own kingdom out there.”

Even if he wasn’t a presence in the town, MJ’s legacy could still help the property fetch a premium price. “If somebody wants to buy it and thinks that because Michael Jackson owned it that has monetary value, it’ll sell for $50 million or above,” says Natale. “It’s going to take somebody that falls in love with it, and then the $100 million doesn’t make any difference to them.”

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