Matthew Perry made a fortune thanks to his time playing Chandler Bing on the hit sitcom Friends, but he also made millions from a robust real estate portfolio.

Before his tragic death at the age of 54, the beloved star had downsized. He sold his properties for a total of $35million over the last years and replaced them with more modest homes – although there’s no suggestion he was in any financial trouble.

Like many actors when they find success, Perry bought his first Los Angeles mansion just one year after Friends premiered in 1994 – a two-bedroom home in the Hollywood Hills

‘It’s the law when you have a successful sitcom: Between the first and second seasons, you buy a house,’ he told the Toronto Star at the time.

It’s not clear for how much he bought it for, but he Canadian-American sold his first mansion in 2001 for $839,000. The property is now worth around $2 million.

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Before his tragic death at the age of 54, Matthew Perry had downsized, selling his properties for a total of $35million over the last years and replacing them with more modest homes

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The Canadian-American purchased a two-bedroom home in the Hollywood Hills a year after Friends premiered in 1994

He had already moved to a new home in 1999, when he bought a 6,500-square-foot mansion in Beverly Hills for a reported $3.2 million. The nearly 2,000 square feet property included a pool and a sauna and glass walls, a feature that would be a part of many of Perry’s future homes.

The actor remodeled the five-bedroom home, which originally had a 1970s aesthetic, and added a screening room, gym, game area, wine cellar and other entertainment outdoor spaces.

Six years after buying the Beverly Hills home, the Friends star sold it for $6.9 million, profiting millions.

Also in 2005, Perry bought a furnished two-bedroom condo on the Sunset Strip for about $2.5 million. The home, previously owned by sir Elton John, was a corner unit in the Sierra Towers building in the West Hollywood area.

In 2006, Perry purchased a 4,100-square-foot mansion on the Sunset Strip for $1.7million. It featured glass walls that opened to a patio and swimming pool as well as multiple fireplaces and a home theater. He sold the property in 2014 for $5.695 million.

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In 2005 Perry bought a furnished two-bedroom condo on the Sunset Strip for about $2.5 million. The home, previously owned by sir Elton John, was  in the Sierra Towers building

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The Friends star looked to Malibu in 2011, buying a $12 million beachfront home called the Pier House, which he once called his ‘kick-ass Malibu home’

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This Pier House in Malibu is where Perry set up an oasis, called the Perry House , which offered holistic services to help men get sober.

In 2008, Perry moved from that glass house to a mansion on Carman Crest Drive that he paid $4.475 million for. The three-bedroom home also featured glass walls and modern architecture.

He sold the house for $4.6million in 2013, but had already moved to a different home by 2011, when he bought another glass-covered three-bedroom home in the Hollywood Hills for $8.5 million.

Also in 2011, the Friends star bought a $12 million beachfront home in Malibu that he once called his ‘kick-ass Malibu home’.

This is the home where Perry set up an oasis, called the Perry House, which offered holistic services to help men get sober. In 2015, Perry made the difficult decision to close the 5,500-square-foot beach compound, overlooking the Malibu pier.

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Mansion in the sky: Perry moved again in 2017 – this time to a ‘mansion in the sky’ with a whopping $20 million price tag.

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The luxurious screening room at the massive penthouse paid homage to Perry’s passion for superhero Batman and is decked out in plush velour furnishings and blackout blinds

The home sat on a generous 2.32 acres of land that offered residents plenty of room to wander around and had an impressive swimming pool, which boasted a breathtaking view out of the ocean, as well as an array of outdoor entertainment features, an admirable large garden area, a fire pit and booming sound system.

‘That was a Malibu beach house, and it was too expensive to run and the business didn’t really work,’ he said at the time.

Perry moved again in 2017  – this time to a ‘mansion in the sky’ with a whopping $21 million price tag.

The 9,290-square-foot home spans the entire 40th floor of the exclusive Century building. Perry hired interior designer LM Pagano to give the four-bedroom, eight-bathroom home an impressive overhaul.

Rihanna bought the mansion in the sky for $21million earlier this year, after Perry originally listed it for $35million.

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In the summer of 2020 he bought a $6 million cottage in the Pacific Palisades neighborhood of Los Angeles

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The Pacific Palisades is home is where Perry was found dead in the hot tub

In 2020, Perry sold his Malibu beach house for $12.95 million – down from the original listing price of $14.95 million but still more than what the actor purchased it for.

That summer he bought a $6million cottage in the Pacific Palisades neighborhood of Los Angeles – where years later he would be found dead in the hot tub.

Initial reports suggested the actor may have drowned, but coroners have yet to confirm a cause of death.

Perry clearly enjoyed the property – which was relatively modest for a star so famous and so wealthy.

His final Instagram post featured him relaxing in its hot tub at night time, which offers gorgeous Pacific Ocean views.

Months before his tragic death, Perry purchased an all-white Mid-century modern mansion in the Hollywood Hills for about $5 million. The three-bedroom, 2,566 square feet home sits on a on a sloped 0.22-acre plot.

The coroner for Los Angeles County has listed Perry ‘s cause of death as ‘deferred’, pending the final results of toxicology tests.

Perry, who played Chandler Bing on the NBC smash hit Friends, had battled substance abuse throughout his life, said that he was keen to help others who were dealing with a similar situation.

In a November 2022 appearance on the podcast Q with Tom Power at Toronto’s Hot Docs Ted Rogers Cinema, he said that the ‘paramount thing’ he would want to be remembered for ‘is that he wants to help people’ battling addiction.

‘The best thing about me, bar none, is that if an alcoholic or drug addict comes up to me and says, “Will you help me?”‘ he said. ‘I can say yes and follow up and do it.

‘When I die, I don’t want Friends to be the first thing that’s mentioned. I want that to be the first thing that’s mentioned, and I’m going to live the rest of my life proving that.’