Every home in Matthew Perry's multi-million dollar property portfolio

In 1995, following the success of the first season of Friends, Matthew purchased a modest two-bedroom home in the Hollywood Hills which he sold in 2001 for $839,000.

"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.

The Fools Rush In actor upsized fairly quickly after his first property purchase, moving into a 6,500-square-foot mansion in Beverly Hills in 1999 before selling his first humble home. 

Matthew reportedly purchased the 1970s home for $3.2 million, doubling its value with the addition of a cinema room, wine cellar, state-of-the-art gym and game area when he sold it six years later. 

In 2005, Matthew's love affair with Malibu began. The star purchased a stunning architectural property known as the 'Pier House' which overlooked the surrounding coastline and Malibu Pier from its hillside Serra Retreat location. 

Characterised by floor-to-ceiling glass walls looking out onto the ocean, a swimming pool and meditation garden, Matthew's zen den was also home to his eponymous Perry House; established by Matthew for addicts, which offered holistic services to help men get sober. 

After it closed, the actor sold the property for $12.5 million.

In the same year, Matthew handed over a cool $2.5 million for a luxe condo on the Sunset Strip, which he reportedly purchased from Elton John.

One year later, the actor 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 an in-house theater. 

He put it back on the market in 2014, making $5.695 million on the sale.

Matthew's main residence in the noughties was his Los Angeles mansion on Carman Crest Drive, which was purchased by the actor in 2008 for $4.475 million. 

Like with many of the star's properties, the three-bedroom home was flooded with natural light thanks to 360 glass walls, as well as an infinity pool and cinema room.

In 2011, the actor purchased yet another home in the Hollywood Hills for $8.5million. At 3,821 square feet with three bedrooms and four-and-a-half bathrooms, this was the Friends star's most expensive property at the time… until he invested in a second Malibu beachfront bolthole later that year.

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

The most exclusive in Matthew's affluent property portfolio is undoubtedly his $21 million penthouse, which was later sold to Rihanna and A$AP Rocky. 

The home, which occupies the entire 40th floor of the The Century high rise, boasts a whopping 9,300 square-feet, for which Rihanna shelled out a casual $21 million.

The penthouse features not one, not two, but four terraces, four bedrooms, eight bathrooms, an expansive living room with floor-to-ceiling windows, an all-white kitchen with marble countertops, dual islands and an adjoining dining space, plus a screening room, separate family rooms and a den, plus a billiards room.

In the days before his tragic passing, Matthew shared several poignant photographs from his beloved Pacific Palisades home. The star bought the $6 million, four-bedroom property in August 2020, and spent his final days there.

SEE: Inside Matthew Perry's $6 million Pacific Palisades cottage he bought just before his tragic death

According to an old listing on Trulia, Matthew's Pacific Palisades property was "perfectly positioned on an ocean-facing bluff top to take advantage of jetliner views of Catalina Island, city lights, sandy beaches and warm sunsets over the blue Pacific." 

Contempo Realtors reported that Matthew bought a stunning Mid-Century modern mansion in the Hollywood Hills as recently as June. 

The actor reportedly got $750,000 off the asking price, making the little-know-about property $5.25 million.