From highest-paid actor to broke: What happened to Charlie Sheen’s property portfolio?

He was once the highest paid actor on TV, earning close to $US2 million ($A3.03 million) an episode on the hit sitcom Two and a Half Men.

At the peak of his career, Charlie Sheen had a staggering net worth of $US150 million ($A227 million), with an impressive property portfolio.

Fast forward to today and the Golden Globe winner’s once-massive fortune has significantly diminished to $US3 million ($A4.5 million).

The Wall Street actor was so broke that he briefly moved in with his parents, living in their guesthouse.

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Here’s a closer look at how Sheen lost his money and what became of his properties.

Two and a Half Men royalties

Sheen was fired from Two and a Half Men in 2011 after he made offensive comments about the series’ creator, Chuck Lorre.

Despite his dismissal, the actor still received $US100 million ($A153 million) in royalties from the show.

However, the lucrative payday didn’t last long as Sheen sold his participation rights for $US27 million ($A40 million) in 2016.

Anger Management deal

In 2012, Sheen returned to television in the sitcom Anger Management, which was based on the 2003 film of the same name.

Charlie Sheen secured a highly profitable deal that granted him 30 per cent syndication ownership (compared to the usual 1-3 per cent) in exchange for a lower per-episode salary.

He was set to earn hundreds of millions of dollars from syndication if the series was successful.

However, poor ratings led to soft syndication demand, and as of 2016, Sheen hadn’t received any payments, making it a significant financial failure for him. The show ended after 100 episodes.

How did Charlie Sheen blow his fortune?

According to Celebrity Net Worth, Sheen lost the vast majority of his former fortune on well-publicised legal costs, child and spousal support payments and extravagant lifestyle expenses.

The Hollywood bad boy also spent millions on hookers and drugs.

In a March 2016 court filing, Sheen claimed to have $12 million in debts, largely attributed to various mortgages.

The Platoon star’s monthly income, which once peaked at $US600,000 ($A907,000), reportedly dropped to around $US167,000 ($A252,000). His monthly medical expenses amounted to $US25,000 ($A37,000).

He disclosed he had paid $US10 million ($A15 million) to settle with people who were blackmailing him about his HIV status over the preceding four years.

Child and spousal support payments

Before September 2016, Sheen paid $US110,000 ($A166,000) a month in spousal support to two ex-wives, Denise Richards and Brooke Mueller.

A judge later reduced the Spin City star’s monthly spousal payment to $US25,000 ($A37,000) per ex, after he sued to have the payments lowered due to his diminished finances.

He also pays about $US500,000 ($A750,000) per year for child support.

In August 2018, Sheen claimed to be in a “dire financial crisis with less than $10 million to his name”.

The actor stated he was unable to make his monthly child and spousal support payments, citing he had “been unable to find steady work and [has] been black-listed from many aspects of the entertainment industry”.

Sheen was seeking to reduce his annual $US1 million ($A1.5 million) child support – $US500,000 ($A750,000) each to Richards and Mueller.

In September 2019, Richards alleged Sheen owed her $US450,000 ($A680,000) in child support, stating he squandered $US24 million ($A36 million) from his Two and a Half Men equity sale, which was intended to settle his personal debts.

What happened to Charlie Sheen’s properties?

Mulholland Estates

In 2011, Sheen paid $US7 million ($A10.6 million) for a Beverly Hills mansion in the exclusive Mulholland Estates gated community. He later sold this property in 2015 for $US6.6 million ($A10 million).

In 2012, he bought another Mulholland Estates home, for which he paid $US4.8 million ($A7.2 million). He sold the residence in 2016 for $US5.4 million ($A8.1 million).

Sheen has also owned properties in Agoura Hills, Sherman Oaks, and Cabo San Lucas, Mexico.

Primary residence

In recent years, Sheen nearly lost his primary Los Angeles residence to foreclosure before finally selling the home at a steep loss.

The Money Talks star paid $US7.2 million ($A10.8 million) for this Mulholland Estates mansion in 2006. He listed it for sale in 2018 for $10 million ($A15 million).

Sheen eventually sold the property for $US6.6 million ($A9.9 million) in January 2020. He took a $US400,000 ($A605,000) hit when he sold a similar home in the same neighbourhood.

The estate gained infamy during the height of Charlie Sheen’s controversial behaviour.

The notorious house where he lived with several girlfriends whom he called his goddesses after separating from Brooke Mueller.

After moving out of his home and living in his parents’ guesthouse, Sheen briefly rented a trailer in an upscale Malibu mobile home park.

The Hot Shots! star has also owned properties in Agoura Hills, Sherman Oaks, and Cabo San Lucas, Mexico.

The actor was last reported to rent a Malibu home in 2022 for an estimated $US16,350 ($A24,800) per month, after selling off most of his Los Angeles properties.

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