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Celebs Who Made Amazing Property Investments

We don’t need to tell you that most of the Hollywood bigwigs are filthy rich. So rich, in fact, that they can buy anything from business houses to islands. While a few seem to be content with whatever they make from their movies and TV shows, there are those who still like to mint more money, while being off-camera. A particular trend is investing their money and trying their hand at the property game. A few cash in big and add to their bottomless money pits while other don’t fare that well. Let’s have a look at those who made it to our ‘Property Investment’ Hall of Fame, and a few who couldn’t be called most investment-savvy celebs.

Jeremy Renner

Mission Impossible actor Jeremy Renner said that he was making more money from his real estate investments at one point of time, more so than he did making movies. This grade-A house flipper has been able to acquire around 24 houses so far, working with his real estate dealer, Kristoffer Winters, invested in upgrading the houses and then selling it off for huge profits. How huge is the profit, you ask? Well, he bought a Holmby Hills house for $7 million and sold it off for $24 million. That should answer your question.

Arnold Schwarzenegger

Before the Terminator actor was the Governor of California or even an actor, Arnold used to make his living by entering and winning body building competitions. And from his savings, he purchased a block of flats, which he sold off to make even better property investments. And guess how successful he got doing this… he actually managed to make a million dollars this way, even before he landed his first acting gig.

Ellen DeGeneres

This Hollywood talk show host has a great real estate investment portfolio, which includes a $15 million profit earned when she sold off her Beverly Hills mansion called Brody House. She also went ahead and bought Brad Pitt’s Malibu pad, flipping it a mere year later for a million dollar profit.

Courteney Cox

This Friends star doesn’t buy houses and then wait for its value too naturally appreciate, she just goes right ahead and makes major renovations and modifications to the estate. This is how Cox is able to turn in a neat profit from each sale. She once bought a house in pricy Beverly Hills for $5.45 million, added a new hall, kitchen, and fixtures and did up the bedrooms. She was able to sell this house for a neat $18 million.

Oprah Winfrey

Daytime talk show legend, business tycoon and Oscar nominee, Ms. Winfrey isn’t so much in the business of flipping properties, but she’s more of a buyer and holder. And what impressive real estate holdings she has! Apart from the various prime properties she has in Atlanta, Florida, Connecticut and Nashville, she also has an oceanfront house in Maui that is said to be worth more than $13 million today.


The late ‘Purple One’ managed to build up a huge property portfolio before he passed away suddenly. There was his Paisley Park home in Minneapolis, Minnesota, apart from owning land and estates in and around Minnesota and even a Caribbean retreat. While his investments ran all the way up to millions, the singer also had his share of financial issues, as some of his properties were close to being foreclosed, as he didn’t seem to be paying their mortgage. A simple mistake, which he reportedly rectified by writing out a $368,000 cheque.

All isn’t this rosy though, as some of our celebs learnt the hard way and saw their investment dreams go awry. Here are some who tried their luck in the property game but didn’t do as well.

Chris Tucker

Tucker is well known for his humorous roles and his Rush Hour movie franchise, in which he acts alongside Jackie Chan. And while we do appreciate his comedic timing and skills to make us laugh for hours, we could not help but feel bad about his financial choices. He was forced to sell two of his mansions in Florida to be able to pay for a long-standing tax bill and avoid foreclosure.

Burt Reynolds

Rough and tough cowboy Burt Reynolds had a disastrous divorce from his wife, actress Loni Anderson, and it really took a heavy toll on Reynolds’ finances. The Smokey and the Bandit star ended up filing for bankruptcy and even had to short-sell his beloved Florida mansion in 2015, which he had purchased way back in the 80’s.

Nicolas Cage

Poor Nic Cage has been ridiculed a lot about his poor financial and property-related decisions. The Ghost Rider actor was once facing a $14 million tax bill which made him dispose off several properties together such as his Bel Air mansion, 2 New Orleans properties, a Las Vegas home, a house in England and an entire castle in Bavaria. Yup, you read that right. We can now understand why the wave of financial issues hit Cage.

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