From Rocky and Rambo to Demolition Man and The Expendables, Sylvester Stallone has chalked up more than his fair share of iconic action movies, and now he's the star of his very own reality TV show, The Family Stallone. The son of immigrants, married three times and a father to five children, Sly's rags-to-riches story is pure Hollywood – but where has he lived along the way? Let's take a look...    

Born 6 July 1946, Sylvester Gardenzio Stallone was born in New York's Hell's Kitchen. Pictured on the right of this photograph aged 11, with his wrestling promoter mother Jackie, younger brother Frank and half-sister Toni-Ann, Sly and his family moved to Washington DC in the early 1950s so his father could open a beauty school. Sly started acting at school and went on to study drama at the University of Miami, where he also began to write.  

In the early 1970s, Sylvester Stallone was trying to make it as an actor, but jobs "did not come easily", in part because of his slurred speech. Now an endearing trademark, his owed his distinctive style of talking to a partially paralyzed face and tongue, the result of an accident at birth. Times were so tough that Stallone became homeless, and it was during this period that he wrote the screenplay for Rocky. But even though he was so hard-up, Stallone refused to sell the script unless he could play the title role, despite having just $100 ($560 today) to his name.

The actor was so broke he even had to sell his treasured dog Butkus. In 2017, he posted on Instagram a photo of himself with his canine pal in 1971 in Hell's Kitchen, New York. "We were both thin, hungry and living in a flophouse above a subway stop," he wrote. "I used to say this apartment had 'hot and cold running roaches'." Stallone rarely went out, and so relied on Butkus for company. "Years later when things got even worse I had to sell him for $40 in front of a 7-Eleven store, because I couldn't afford food." Then, "like a modern day miracle," he sold the Rocky screenplay and bought him back... for $15,000. "He was worth every penny!"

Shot in just 28 days, Rocky was made for less than $1 million, but went on to become the highest-grossing film of 1976. Winning three Oscars, including Best Picture, it launched Stallone's career and he went on to star in five sequels, as well as the Creed spin-offs. Alongside Arnold Schwarzenegger, Sly became the major action movie star of the 80s and 90s. 

From the late 1950s, the young Sylvester lived with his family in this four-bedroom brick-built Cape Cod-style home in Silver Spring, Maryland, just 25 minutes north of Washington DC. The family lived in the area for around a decade before Sly began college and the family moved on. It most recently came onto the market in 2020 and sold for $699,000. 

In 1976, after a stint of homelessness in both New York and Los Angeles, the young actor hit the big time with Rocky. From the late 70s he lived in Malibu, where he spent his downtime painting. Sly lived in the upmarket beachside community with his then wife Sasha Czack and their two sons, Sage and Seargeoh.  

A keen artist and sculptor, Stallone believes he's "a much better painter than an actor. It's much more personal and I'm allowed to just do what I want to do." He has exhibited his work at Art Basel and The State Russian Museum, and he's also an avid art collector. The stairs of his Malibu home were lined with works including Sijan's 'Girl in Arched Mirror' and Kunc's 'Factories in the Sun'. 

In 1982, Stallone took on what was to become another defining role – that of John Rambo in First Blood. Not long after, in 1985, Stallone and Czack divorced and that same year Sly married model and actress Brigitte Nielsen. A year later, the star – who was a keen polo player – bought White Eagle Ranch in Hidden Valley, California. 

When Stallone bought the property, there was only a six-stall stable block and a two-bedroom cottage on the site. Sly added a floodlit polo field, two swimming pools, a guest house, gaucho accommodation, a guard house and a 7,500-square-foot, two-story lodge. True to style, distinctive art featuring the actor hung on the walls. The multi-talented star still owns the LeRoy Neiman painting you can see in this photo – you might just spot it in another of the homes we'll tour...

In 1990 he listed the 23-acre ranch for just shy of $7.8 million, finally selling it in March 1992 for $4 million in cash. According to his realtor at the time, Stallone sold the ranch “because he was shifting his interests and not utilizing the polo ponies”. She added: “I think he’s still a great lover of horses, but he moved a lot of his horses last year to his ranch in Maryland", hinting that he still owned a home in the state he grew up in. That same year, he bought 160 acres in Telluride, Colorado, as well as 11 lots on a Telluride ski run. The property mogul also owned a home in Kauai, Hawaii from 1988 to 1996, as well as a polo field and several parcels of land, which he developed and sold off.

Stallone's father Frank served in the US Army cavalry and played polo in the 1950s, instilling in him a love of horses. Sly said during an interview with Oprah in 1989 that "playing polo is like trying to play golf during an earthquake". While shooting buddy cop movie Tango & Cash the year before, he even gave co-star Kurt Russell a polo lesson. "He really is good," Russell said. "He's a very good teacher." Stallone revealed recently that his daughters are also keen equestrians.

Stallone wasn't content with just making movies and playing polo while he lived in Hidden Valley. He was also the original developer of the upscale White Stallion Estates enclave in the area. The 250-acre community is split into 12 large lots, each surrounding an incredible home. There are French Chateaus, English country estates and Mediterranean mansions, as well as horse ranches like Sly's. Celebrities including Britney Spears and Ellen DeGeneres have owned homes there at one time or another.

It was around this time, in 1987, that Stallone and Nielsen divorced after just two years of marriage – but it wasn't long before Sly found love again. He met model Jennifer Flavin in 1988 and they dated off and on until finally marrying in 1997. Together they have three daughters, Sophie, Scarlet and Sistine. In August 2022, Flavin filed for divorce but just one month later the couple put a halt to the proceedings. “Let’s just say that it was a very tumultuous time,” Sly told The Sunday Times. “There was a reawakening of what was more valuable than anything, which is my love for my family.” The star has confirmed his new reality series will document their troubles.

In 1993, the actor bought a neoclassical-style villa in Miami. Overlooking Biscayne Bay, the house is set in 14 landscaped acres, which included a pool, ponds, waterfalls, fountains and formal terraced gardens. Inside, the incredibly opulent interior was brimming with antiques and artwork by Rodin, Bacon and Faléro. As Stallone told Architectural Digest in 1997, the interior design was inspired by Versace's "baroque fantasies" and carried out by Italian Massimo Papiri. "Go for it," Stallone told him. "Rococo me to the max." The atrium of the palatial pad was "inspired by the Danieli in Venice", while the walls of the staircase took after "the ochre stucco in the Sistine Chapel". He sold the lavish home in 1999, reportedly for around $16.2 million after purchasing it for $8 million.

Since the late 1990s, the Rambo star has lived with his family in this stunning eight-bedroom, 12-bathroom mega-mansion in LA's prestigious Beverly Park. Over the years, Stallone added an art studio, guesthouse, cinema, bar, gym and cigar room with an air-filtration system.

The house even had a memorabilia room, with shelves full of Rocky and Rambo merchandise, as well a life-sized Rocky statue and that distinctive artwork he used to house in his Malibu pad back in the 80s. 

Steel-framed windows make the most of the views from the opulent bar area, which is once again dominated by a LeRoy Neiman artwork of Rocky and Apollo Creed duking it out, while two smaller bronze boxing sculptures perch on glass coffee tables in the lounge area.

A more formal reception room, this bright space has a baby grand piano and a pool table for entertaining guests, while yet more colorful artwork adorns the walls, including a 'Two Sides of Sly' by Andy Warhol, which the actor has owned since the 80s. Sly also owns pieces by Claude Monet and Francis Bacon, and used to own two Rodin sculptures, including 'Iris', which he bought in 2007 for $5.7 million, then a record for a Rodin. He sold it for $14.4 million at Sotheby's in 2016.

The pool has incredible views over the Franklin Canyon Mountains. Flanked by a putting green, it was even adorned with a Rocky statue when Sly lived there. In February 2022, the Rambo actor sold the house to superstar singer Adele for $58 million – a painful price drop from the $110 million he originally listed it for in January 2021. The actor may also wince at reports Adele has completely torn down the whole pad, with just his Rocky statue still standing. Ouch. 

In 2010, the writer and director bought this four-bedroom Tuscan-style villa in La Quinta, a desert resort city in Coachella Valley, California. Tucked away in the exclusive Madison Club, the home boasts marble pillars, high beamed ceilings and hardwood floors. 

Strong Mediterranean influences abound, from carved wooden doors and wide arched entryways to the white walls and wrought-iron details. Built by Stallone in 2008, his Italian-American heritage may have influenced the style. 

The imposing grate room features an antique chandelier and impressive carved stone fireplace. The double-height room gives way to a tiled kitchen and dining room beyond. Although his tastes have certainly simplified since he lived in his rococo palace in Miami, it just wouldn't be Sly's home if it wasn't scattered with bold pieces of art and sculpture.

The spacious master bedroom has a fireplace, private balcony and marble ensuite, as well as a wooden four-poster bed with mirrored canopy. In a very Hollywood touch, the TV rises from the foot of the bed. Outside, the view encompasses dense palm trees that give way to a mountainous horizon.

The outdoor set-up must have been perfect for a family barbecue, with covered outdoor kitchen, a fountain-fed swimming pool, hot tub and firepit. The garden even has its very own man-made creek. Sly sold the villa in June 2021 for just shy of $3.2 million, about $1.2 million less than he paid for it a decade before and after trying to unload it in 2014 for $2.4 million. 

In July 2012, just after he bought his La Qunita home, Sylvester's family were hit hard by the tragic passing of his eldest son, Sage – seen here with his father in a scene from Rocky V. Sage was 36 when he died suddenly of coronary artery disease. "When a parent loses a child there is no greater pain," Stallone told TMZ in a statement. "Therefore I am imploring people to respect my talented son's memory and feel compassion for his loving mother Sasha. This agonizing loss will be felt for the rest of our lives," Stallone said. "Sage was our first child and the centre of our universe and I am humbly begging for all to have my son's memory and soul left in peace."

In December 2020, Flavin and Stallone dropped just shy of $36 million on this Caribbean-style mansion in Palm Beach. With seven bedrooms, 10 bathrooms and 250 feet of beach, it's nestled in a lakefront compound on the far North End of town. Neighbors include Jon Bon Jovi, Rod Stewart, Rush Limbaugh and shock jock Howard Stern. 

Built in 2014, the Caribbean-style home stands on 1.5 acres and includes a pool pavilion and guesthouse. The sellers told Palm Beach Daily News that the estate is "fantastic" and well suited to family living. The publication also reported that Sly financed the sale with a $15 million 30-year mortgage. 

Inside, the décor has a contemporary feel, with floor-to-ceiling windows, a neutral color scheme and pale wood ceilings. Unsurprisingly for an action hero – even a 76-year-old one – the house is equipped with a large, fully decked-out gym, as well as a temperature-controlled wine room. 

The plush residence has seven bedrooms and 12 bathrooms. The impressive master suite has a private balcony with ocean views, as well as a luxurious bathroom and enormous walk-in closet, complete with chandelier and balcony.

Outside, the beautiful gardens are dotted with palm trees. An elegant poolside pavilion is the perfect place to entertain or shelter from the sun. The keyhole-shaped pool gives way to a beach-edge hot tub, with white sands and a jetty beyond. During their brief split, Flavin reportedly filed a petition for the dissolution of their marriage. In it she alleged that Stallone had engaged in the "intentional dissipation, depletion and/or waste of marital assets which has had an adverse economic impact on the marital estate". She reportedly requested exclusive use of the Palm Beach estate.

In February 2022, Sly bought this elegant Hamptons-style equestrian estate for $18.5 million. Then, just 10 months later, he put it back on the market at $22.3 million – a considerable mark up for such a short space of time. After delisting it in February, it's now been reduced to $21.3 million. Built in 2014, the listing describes it as a "true gentleman's ranch", with a four-stall horse barn, beautiful tack room and a private riding ring. 

The estate is the second Sly has owned in the Hidden Hills area, and it's enclosed behind private gates at the end of a quiet cul-de-sac, the perfect pad for a celeb looking for a peaceful retreat. The gardens feature a pool, hot tub and pool house with outdoor kitchen, as well as a self-contained guesthouse and an orchard with a wide variety of fruit trees. Savvy Sly has even taken California's soaring temperatures into account and filled the grounds with drought-tolerant landscaping. 

Inside, the four-bedroom, eight-bathroom home is light and airy, combining clean white walls with dark wood accents. The open concept chef's kitchen flows into the grate room, while elsewhere the house boasts a home theater, fully-equipped gym and sauna. 

The fairytale master suite is fit for a princess, with a large stone fireplace and four-poster bed draped in pale pink curtains – even the balcony is curtained, guaranteeing perfect privacy. The large ensuite bathroom has his and hers basins, a marble shower and freestanding bath under a crystal chandelier. The enormous walk-in closet and dressing room features additional chandeliers, and even a TV.

The horse barn is made up of four stalls that are connected to a large entertaining space, which actually opens into one of the stalls, so your equine pal can poke their head through and say hi as you relax after a day of riding. The room has a fully equipped kitchen, with a wood-burning stove and an Aga range (an interesting choice, considering the warm climate). The house has featured heavily on the Stallone family's social media and we may see more of it in their upcoming TV show. According to the Mirror, the macho star even threatens to destroy the home in an upcoming episode. 

The superstar has played dozens of roles over his long career, and he's currently playing the lead in Tulsa King as well as taking on the entirely new role of reality TV star. The Family Stallone lifts the curtain on Sly's homelife with wife Jennifer Flavin and their three daughters, Sistine, Scarlet and Sophia. The show premiered in May 2023 on Paramount+ to middling reviews. One reviewer branded it "trash television," but added that – as Stallone was "one of the most likeable people to ever swagger in front of a camera" – the show was "eminently watchable." 

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