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The Most Expensive Hollywood Homes In History

Being rich and famous comes with some obvious perks. The biggest one – literally – is probably your economic capacity to dream up whatever insane house you can think of and have it built or buy it without blinking twice. They can have all the swimming pools, gyms, libraries, rooftop helipads and whatever else they think they need in a house.

Naturally, this exclusivity comes with a huge price tag. Let’s take a look at some of the most expensive Hollywood homes we’ve seen in history over the years.

Taylor Swift – Beverly Hills

When it comes to real estate, Taylor Swift has one of the bigger portfolios in Hollywood. The biggest item in her collection is probably her $30 million property in Beverly Hills that was built all the way back in 1934 and offers all the luxury one could need in a 11000 square foot space.  

Tiger Woods – Jupiter Island

One of the most successful golf players in history, Tiger Woods has had no shortage of cashflow in his career. He owns quite a bit of real estate but one of his favorite homes is his Jupiter Island mansion and it’s not hard to see why. The mansion is built out of six bunkers, ranging from 3300 square feet to almost twice that, that each serve a different purpose.

Beyonce & Jay-Z – Bel Air

Remember when we had a comedy sitcom about a black family living in Bel Air? Well, it’s reality now. Queen B and Jay-Z have amassed over $1 billion in wealth, so this $88 million mansion isn’t breaking their bank at all. It was originally listed at $120 million but the couple negotiated an amazing deal for this insane property.

Oprah Winfrey – Montecito

Oprah’s house goes at a whopping $88 million and genuinely looks like some kind of royal palace. The house is named “Promised Land”, and is built on a 42 acre plot of land. The house already existed when Oprah bought it so this wasn’t a custom made job. She bought it in 2001 for $52 million, slightly over half of the price it’s valued at today. What a great investment!

Kylie Jenner – Holmby Hills

One of the more successful members of the Kardashian clan, Kylie has managed to amass quite an amount of wealth despite only being in her 20’s. She’ll never have to work again for the rest of her life, and she can spend all that time just chilling out her in her $36,5 million Holmby Hills mansion. It even has game rooms and an indoor theater so why even leave in the first place?

Lady Gaga – Malibu

Another celebrity with quite a few properties under her belt, Lady Gaga’s most impressive house is probably her Malibu mansion. It’s currently valued at $23 million and it’s not exactly what you’d expect from maybe one of the more eccentric stars of the latest decades. It’s just a very neutral and soft mansion, probably perfect to unwind in.

Howard Stern – Palm Beach

It always surprises me how much money Howard Stern has made when most of his career was just him making shocking radio. I guess if you’re the first and the best at something, there’s huge amounts of money to be made no matter what it is. One of Stern’s biggest mansions is his $52 million property in Palm Beach, on which he even spent $13 million on renovations alone!