12 Celebrities With Insane Property Portfolios

·20 min read

Hollywood stars and billionaires have long set the standard for what a dream home would look like. I’m talking in-home movie theaters, 10-car garages, spas and steam rooms, tennis courts — the list goes on. But there’s an extra level of high class that sets these famous landowners apart: those who own five or more homes. Read on for all the stars who have insane property portfolios and are a part of the exclusive five-and-over club.

1.Leonardo DiCaprio: five homes, two condos, one island

Leonardo DiCaprio posing for the camera in a tuxedo

It’s safe to say Leonardo DiCaprio has come a long way from his modest childhood home in Los Angeles, California. The movie megastar began his career when he was just 5 years old, and through the decades he has become one of the most successful actors in the world, with an estimated net worth of $260 million. With his fortunes, DiCaprio has made it clear that real estate is one of his greatest passions and favorite way to splurge.

The Once Upon a Time…In Hollywood star can’t resist the California charm, where he owns five of his homes, in addition to several luxury condos in Manhattan. He also owns a $1.75 million private island in Belize, where he intended on building Blackadore Caye eco-resort, but the dream never came to reality.

His California properties include a $5.2 million Palm Springs midcentury-modern mansion (7,000 square feet, 6 bedrooms, 7.5 baths, tennis court, and guest house), a $2 million Hollywood Hills home formerly owned by Madonna (12,530 square feet, 5 bedrooms, 8.5 baths, and a basketball court), a $23 million home on Malibu’s Paradise Cove (1.76 acres and 90 feet of beach frontage), and a $13.8 million oceanfront house elsewhere in Malibu (3,268 square feet, 4 bedrooms, 5 bathrooms).

In 2021, DiCaprio sold his historic Los Feliz home to Los Angeles-native Miguel for $4.9 million. Later that year, he purchased Gwen Stefani’s old Los Feliz mansion from Jesse Tyler Ferguson for $7.1 million and an iconic $10 million estate in Beverly Hills. His main residence remains a three-house, four-parcel compound way up in LA’s Bird Streets in Hollywood Hills, which includes the house formerly owned by pop icon Madonna.

Jeff Kravitz / Via FilmMagic

2.Taylor Swift: eight homes

Taylor Swift smiling at the camera wearing a velvet dress

Taylor Swift owns at least $84 million in real estate across four states and a grand total of eight homes — that we know of. The pop superstar has been collecting properties across the United States since she was 20 years old. In 2009, she purchased her first home for $1.99 million, a 3,240-square-foot condo in the heart of Nashville’s Music Row, now worth about $3 million. Two years later, she bought an estate in Nashville for $2.5 million, this time in the quiet Forest Hills suburb. It features four bedrooms and four and a half bathrooms, as well as a 2,000-square-foot guest house adjacent to an impressive outdoor pool.

In 2011, she purchased a Cape Cod-style cottage in Beverly Hills for $3.55 million. She sold the three-bedroom three-and-a-half-bathroom house for $4 million in 2018 before her Reputation tour. In 2012, she purchased a $1.78 million single-story home with a pool, a 1,000-bottle climate-controlled wine cellar, and a private courtyard and garden. She sold the home in 2018 for $2.65 million

In 2013, the Grammy winner purchased a 12,000-square-foot mansion in Watch Hill, Rhode Island for $17.75 million, followed by a $20 million duplex penthouse apartment in NYC’s Tony Tribeca Neighborhood in 2014. Swift topped it off with a $25 million Beverly Hills mansion in 2015.

A double penthouse is clearly not enough space for a queen like Swift. So, the megastar bought an $18 million townhouse in 2017 directly next door to her double penthouse, plus a $9.75 million apartment in the same building. Her total real-estate holdings on this one Tribeca block alone is roughly $47.7 million.

Dimitrios Kambouris / Via Getty Images

3.Kanye 'Ye' West: 10 homes

Kanye West smiling and wearing a denim puffer coat

As Kanye 'Ye' West began to emerge as a solo rap artist and producer, he purchased his first home in Hollywood Hills in 2003, marking the start of his property journey. As his debut album skyrocketed in 2004, Kanye purchased a bachelor pad in Soho New York. He bought the 1,500-square-foot unit for $1.9 million, and in 2006 bought the apartment next door for $1.25 million.

In 2013, Kim and Kanye bought their first home in Bel Air for $11 million. After marrying Kim in 2014, the newlyweds purchased their extravagant Hidden Hills mansion for $20 million, not including the additional $20 million in renovations.

After news of Kanye’s divorce in February 2021, Kanye fled to his Wyoming ranch retreat, which he bought back in 2019. He also owns a second Wyoming ranch, located near Greybull, Wyoming, about an hour away from his first ranch. This place is known as Kanye’s therapy ranch, where he spent time writing lyrics in the wake of his split with Kim.

To add to his extensive property portfolio, Kanye owns a home in Calabasas, set on just over one acre of land, and a concrete beach home in Malibu bought in September 2021 for $57 million. Most recently, in 2021, Kanye made a real estate purchase that raised eyebrows. The rap star purchased a mid-century Hidden Hills estate right across the street from Kim Kardashian for $4.5 million.

Edward Berthelot / Via Getty Images

4.Rihanna: just shy of a dozen

Rihanna smirking at the camera wearing bright red lipstick and a green dress

Between her successful music career and business in lingerie and beauty, Rihanna is worth an estimated $600 million. It’s no surprise that she has rented and owned homes worth over a $100 million, from California, New York, England, and Barbados. In March 2021, she dropped $13.8 million on a Beverly Hills mansion built in the 1930s, located in the Post Office district. Just a few months later, she dropped $10 million on the property directly next door.

In September 2020, Rihanna’s former residence in London hit the market for $41 million. Yes, you heard me right. The 19th-century home featured eight bedrooms, a gym, screening room, a private elevator, and a parking lot that can fit up to 10 cars. RiRi rented this property for £18,000 a week, or $25,000 —meaning she paid $100,000 a month to stay here. Real hot girl sh*t. Oh, to top it off, earlier that year she rented a 6,140-square-foot home in Southhampton for $415,000 a month.

In 2015, Rihanna dropped $925,000 on a 2,000-square-foot condo in a Los Angeles high rise along the Wilshire Corridor. In 2013, Rihanna purchased a $21.8 million 10,000-square-foot beachfront property in her home country of Barbados. The condo is part of One Sandy Lane, a luxury resort in Paynes Bay. Since 2017, Rihanna has owned a luxury penthouse in The Century building in Century City. She also purchased a Mediterranean-style mansion in the Hollywood Hills back in 2017, for $6.8 million.

From 2013–17, the singer rented a $50K-per-month penthouse in New York, New York, and on the west coast, she rented a $65K-per-month mansion in Pacific Palisades in 2012. In August 2017, she paid $2.7 million for a Mediterranean-style villa in West Hollywood. Less than three months later, she flipped the property and sold it for $2.85 million.

Rich Fury / Via Getty Images

5.Jeff Bezos: 30K-acre ranch, one museum, too many homes to count

Jeff Bezos giving a speech on stage holding a microphone

Former Amazon CEO Jeff Bezos remains the richest person in the world, with an estimated net worth of $140 billion. He has spent millions of dollars amassing a massive real-estate portfolio across the US, from his home state of Washington to New York City. In June 2019, two months after he and his ex-wife MacKenzie announced their divorce, Jeff Bezos dropped about $80 million on three adjacent New York City apartments. This included a three-story penthouse and two units directly below it, marking it the most expensive real-estate deal south of 42nd Street in New York. He also owns a handful of other properties in New York.

Bezos also owns two homes in Medina, Washington, spanning roughly 5.3 acres. He paid $10 million for the first property in 1998, which is a 20,600-square-foot, 5-bedroom, 4-bathroom house. The other is a 8,300-square-foot 5-bedroom, 4-bathroom home for which he paid $53 million.

Bezos also owns property in Beverly Hills, one of the most expensive neighborhoods in Los Angeles. In 2007, Bezos bought a Spanish-style mansion for $24.45 million, consisting of seven bedrooms, seven bathrooms, a greenhouse, a tennis court, a swimming pool, four fountains, and a six-car garage. It literally can’t get any more dreamy. And because this estate is clearly not big enough, 10 years later he bought a “modest” 4,568-square-foot house next door for $12.9 million.

In 2020, Bezos bought the Warner Estate, originally designed for the former president of Warner Bros., Jack Warner. He bought the 9-acre property for $165 million, marking it the most expensive home ever sold in Los Angeles. Bezos also owns a 30,000-acre ranch about 30 miles from the town of Van Horn, Texas. In 2016, Bezos bought a former textile museum in Washington, DC for $23 million. Not only is this property on the National Register of Historic Places, but the 27,000-square-foot mansion is the largest home in Washington, DC. In January 2020, Bezos bought a four-bedroom home directly across the street.

Kevin Mazur / Via Getty Images

6.Madonna: six homes

Madonna attends a celebration of the Lola bag, hosted by Burberry & Riccardo Tisci on April 20, 2022 in Los Angeles, California.

From her 18th-century mansion in Portugal to her reported six properties in and around London, it’s obvious Madonna has an insane property portfolio.

In 2007, Madonna continued to expand her holdings in the UK. She purchased a 10-bedroom town house for $8 million from designer-developer Paul Davie in Marylebone — one of London’s poshest spots to live. This marked her sixth London property; the others included a family townhouse, two cottages for her staff, and two properties for use by Kabbalah groups.

One of the pop singer's most notable homes is her $40 million Upper East Side apartment in New York City, purchased in 2009. The singer bought the two neighboring houses and had all three combined to make the ultimate New York abode for herself and her kids. The townhouse includes a two-car garage, a king-sized library, nine fireplaces, an elevator, and a climate-controlled wine cellar.

Since the pandemic began in 2020, Madonna and her family have been spending time in sunny LA. But recently, Madonna has put her Hidden Hills mansion on the market for $26 million. She purchased the nine-bedroom house in April 2021 from The Weeknd for $19.3 million.

Stefanie Keenan / Via Getty Images

7.Elen DeGeneres: about a dozen mansions, but has commitment issues

Elen DeGeneres and partner Portia de Rossi smiling

Ellen DeGeneres and partner Portia de Rossi have bought and sold upward of 20 properties since 2003. Her real-estate portfolio began when she bought a Hollywood Hills home for $6 million in 2003, the same year she began The Ellen DeGeneres Show. She sold the four-bedroom, four-and-a-half bathroom home to Will Ferrell three years later for $9 million. In 2004, the same year the couple began their romance, they bought a mid-century-style home in Hollywood Hills nicknamed “the treehouse” for just over $1.2 million. A year later they sold it to actor Heath Ledger for $2.1 million.

In 2007, the couple acquired a mansion in Montecito, California for $15.75 million and sold it for $20 million. A year later, the dynamic duo leveled up their holdings by purchasing a $29 million 9,200-square-foot property and then bought two homes right next door to add to the estate. They also own an $8.5 million horse ranch in Thousand Oaks, California they bought that same year and sold it for $10.85 million in 2013.

There were countless other homes bought and flipped by DeGeneres and Rossi in the years between, but the most iconic ones I’ve saved for last. In 2017, they dropped $7.2 million on a historic property in Montecito. Less than a year later, the couple sold it to Tinder founder Sean Rad for $11 million. In early 2019, the couple dropped $27 million on a 5-bedroom, 10-bathroom Balinese-style Montecito mansion known as the Salt Hill estate. The following year, they let this property go for a whopping $33 million.

In 2020 they bought a three-bedroom Tudor in Montecito, which was originally built in England in the 1700s and later brought over to the United States. DeGeneres and de Rossi paid $3.6 million for this iconic place, but a few months later in June 2020, they sold it for nearly double that price to buyer Ariana Grande. In September, they purchased a 4-acre property in Montecito for $49 million. The property had multiple buildings, including a Cape Dutch-style main house and a barn designed by Tom Kundig.

In May 2021, DeGeneres and de Rossi decided to re-buy the historic Montecito property they sold in 2017. They paid $14.3 million, just short of double what they originally paid. Just one month later, they dropped $2.9 million on a small seaside bungalow not far from Butterfly Beach. As of this year, DeGeneres owns about half a dozen homes in Montecito alone.

Kelly Sullivan / Via Getty Images for RH

8.Oprah Winfrey: at least six homes

Oprah Winfrey at arrivals for The 20th Annual Screen Actors Guild Awards (SAGs)

It is no surprise that media mogul, philanthropist, and producer Oprah Winfrey currently owns at least six homes. As of 2021, she has amassed a net worth of $2.5 billion. Though she has been calling Montecito, California home for more than 20 years, Winfrey has also owned homes in Miami, Chicago, Atlanta, Maui, Telluride, Colorado, and Orcas Island, Washington. She has also purchased property for family and friends in Tennessee and Indiana.

Winfrey purchased her 42-acre home in Montecito for $50 million, which included a 23,000-square-foot Georgia-style house, a 6,000-square-foot guesthouse, a tennis court, a pool, and many patios. In the decades following, Winfrey bought nearby properties to expand her holdings in Montecito. The most recent addition was in 2019, when she purchased a 4-acre complex from actor Jeff Bridges for $6.85 million, expanding her ranch to 70 acres.

Although Winfrey has sold countless of her properties throughout the years, it is believed she still owns at least six homes across the United States.

Elizabeth Goodenough / Via Everett

9.Chrissy Teigen and John Legend: eight homes

Chrissy Teigen with husband John Legend at the 64th annual GRAMMY awards

Model Chrissy Teigen and singer John Legend have a pretty legendary property portfolio, from the Big Apple to West Hollywood. Before meeting his future bride, in 2005 Legend purchased a 1,105-square-foot two-bedroom, two-bathroom New York City apartment in the East Village. In 2007, Legend purchased an earthy ranch house in Hollywood Hills for $1.5 million soon after he met Teigen on the set of a music video. They sold the three-bedroom, two-and-a-half-bathroom home for $2 million in 2014, shortly after they married. In 2009, when the couple was only dating, they purchased a two-bedroom, two-bathroom condominium in the Bowery section of Manhattan for $1.9 million. They added a walk-in closet for Teigen and a music room with a Yamaha piano for Legend. They sold the pad for $2.68 million in 2012 for $3.2 million.

In 2016, the Teigen-Legend family purchased an 8,520-square-foot Beverly Hills house for $14.1 million in 2016 before putting it on the market in August 2020 for $17.7 million. After selling their one-bedroom condo in 2016, they returned to New York City to buy two penthouses in a historic 1856 building. The couple purchased the south penthouse for $9 million in 2018 and the north penthouse for $7.7 million in 2020. Together, both penthouses offer six bedrooms and six bathrooms, an office, a media room, and a private landscaped roof terrace with an outdoor kitchen. As of recently, the couple has found a buyer for their $18 million pair of NYC penthouses.

The duo bought a modest 3,440-square-foot home in West Hollywood for $5.1 million in April 2020. The 0.14-acre lot has a pool, a spa, a guest house, and floating gardens with built-in drip irrigation. Later that year, they purchased a 10,700-square-foot estate for $17.5 million in Beverly Hills.

Axelle / Via FilmMagic

10.Adam Levine: seven homes

Adam Levine of Maroon 5 performing live

Los Angeles native and lead singer of Maroon 5, Adam Levine, owns homes in expensive neighborhoods like Beverly Hills and Pacific Palisades to a luxury apartment in New York. In 2005, Adam Levine purchased a modern bachelor pad in Hollywood Hills for $3.1 million before meeting his now-wife Behati Prinsloo. The home featured a home theater, two fireplaces, a gym, and stunning views of Hollywood from the floor-to-ceiling windows. He sold the property in 2013 for $3.5 million. In 2012, Levine purchased another bachelor pad for just over $4.8 million in Beverly Hills. The ranch-style mansion had five bedrooms, seven bathrooms, a high-end kitchen, a pool, a spa, a gym, and a screening room. All the things to fit Levine’s laid-back lifestyle. He sold the property to friend John Mayer in 2018 for $13.4 million.

Levine and Prinsloo chose to make the move to the East Coast in 2014, purchasing a $4.5 million apartment in SoHo, New York. The apartment is set in the early 1900s cast-iron building and has an old industrial feel. The one-bedroom, two-bathroom loft sold in 2016 for $5.5 million. Levine purchased a French Regency-style estate built in the 1960s for $18 million in 2017. The five-bedroom home sat on 1.2 acres of land and had five bathrooms, a two-story guest house, a pool cabana, and a garage. The couple put the house on the market six months later, once they found out they were expecting their first child.

The most expensive home Levine owns is a Tudor-style mansion he bought from Max Mutchnick, the co-creator of Will and Grace. The $35.5 million estate was built in the 1930s and features seven bedrooms, eight bathrooms, a media room, gym, two kitchens, a theater, and a guest house. Levine ended up selling the property to Ellen DeGeneres for $45 million in 2019.

In early 2019, Levine purchased a 1930s three-structure compound in Pacific Palisades from Jennifer Garner for $32 million. The main structure of the house features five bedrooms and two bathrooms. The second structure features an office, a screening room, a gym, and a yoga studio. The third structure is a two-story guest house. Levine and his wife still own the property and consider this their primary residence.

The latest addition to Adam Levine’s real estate portfolio is a historic Montecito home he purchased at the beginning of 2021 for $22.7 million. The 5.2-acre villa-style property is located in Santa Barbara County and features nine bedrooms, a tennis court, a swimming pool, and a five-car garage.

Guy Prives / Via Getty Images

11.Beyoncé and Jay-Z: seven owned, handful of rentals in the mix

Beyonce holding hands with husband Jay-Z on stage

When it comes to celebrity power couples, it doesn’t get any better than Jay-Z and Beyoncé. The billionaire duo owns multiple homes and luxury acquisitions. Beyoncé used to own a four-bedroom three-and-a-half-bathroom abode in Houston; she sold it in 2012. Jay-Z used to own a two-bedroom apartment in Brooklyn that spanned over 1,000 square feet. He sold put it on the market for $1.4 million in 2016. In 2008, Jay-Z purchased a loft in Tribeca for $6.85 million. It was the source of a media frenzy when paparazzi discovered that it was the Carters’ secret wedding location. Before Beyoncé tied the knot with Jay-Z, she bought a Midtown Manhattan condo for $5 million in 2005. The home boasts three bedrooms and three-and-a-half bathrooms at 2.699-square-feet. After owning the property for 12 years, she sold the unit for $9.95 million in 2017.

The couple has also had multiple rentals over the years, including Jay-Z’s Time Warner Center Manhattan rental, a Miami rental, a Bridge Hampton rental, and a maternity Malibu rental. In 2015, the Carters’ also had a residence in the Garden District of New Orleans. Known as La Casa de Castille, the mansion included quirky features, such as a set of floor-to-ceiling bookshelves and a unique rooftop garden. The home was worth $2.6 million before a fire broke out in 2021 due to arson.

Bel-Air had always been a dream home location for the couple, so in 2017 they made their dreams a reality, purchasing a 30,000-square-feet compound for $88 million. Not too long after this purchase, they bought a $26 million seaside house in the Hamptons. It’s located in the extremely wealthy and exclusive neighborhood Georgica Pond, whose residents include Martha Stewart and Steven Spielberg.

Kevin Mazur / Via Getty Images

12.Jennifer Lopez: six homes

Jennifer Lopez and boyfriend Ben Affleck

This mom of two owns houses across the US from Miami to Manhattan worth an estimated $97 million, including some she still shares with her former fiancé Alex Rodriguez. In case you weren’t already aware, things are spicing up between Ben Affleck and Jennifer Lopez. The power couple recently opened escrow on a $55 million Bel Air Estate.

Lopez also owns a jaw-dropping waterfront retreat in Miami’s Star Island with Rodriguez. The former couple bought the home in 2020 for $32.5 million. It has 10 bedrooms, 10.5 bathrooms, and stunning ocean views. The former couple also own a comfy cottage in Encino, Los Angeles. The $1.4 million home features a modern kitchen and three bedrooms, including a master suite with a walk-in closet and brand-new bathroom. In 2016, Lopez bought a $28 million Bel-Air mansion and still owns it today. The estate is complete with its own pub, two guest cottages, and an amphitheater that seats 100 guests.

Following her divorce with Marc Anthony in 2014, Lopez bought a $20 million penthouse in Manhattan that feature four bedrooms and a terrace overlooking Madison Square Park. The Hamptons is known to be a top destination for the rich and famous, so of course Lopez had to plant her roots here. She bought an eight-bedroom home here in 2013 for $10 million. It has a sauna, a steam room, a swimming pool, and a home cinema. She still owns it today.

Stephane Cardinale - Corbis / Via Getty Images