Chelsea Handler | House Tour | $5.8 Million Brentwood Mansion & More

Stand-up comedian, actress, author, and late-night cable talk show host Chelsea Handler is probably best known for her numerous Netflix specials and for hosting the very popular Chelsea Lately series. In fact, in 2012, Chelsea had already made such an impact on the world of comedy, Time Magazine honored her by naming her as one of the most 100 most influential people in the entire world. Just about two years prior to earning that accomplishment, Chelsea bought herself her own little reward, a $6 million home situated above the Bel Air Country Club in Los Angeles, California. In these videos, we don't reveal any addresses, and even though I've done a house tour of my own place, please do not show up at any private residences because it's not safe for anyone. Chelsea Handler invited Architectural Digest into her home to show off her numerous design choices and the upgrades she's made over the years. She also gave them a little bit of background as to why she chose to update this house in the first place, telling them, It's my first house that I've ever bought. There was just a lot of closed-off spaces, and I wanted open spaces, and I wanted indoor-outdoor living because why else are we living in California if we don't get all of those things? Situated on a tiny cul-de-sac and all but invisible behind tall redwood gates, Chelsea's longtime property was technically a contemporary-style box home, but its aesthetic choices definitely have more in common with an exotic retreat. For instance, the entire half-acre lot is covered in lush, subtropical landscaping, not to mention boasting a jungle-like front entryway. All 5,572 square feet of the home's interior have been extensively and expensively retrofitted by Chelsea, and it's now largely defined by its vast walls of glass and expansive gathering spaces that include a fireplace-equipped living room with lighted, built-in shelves. A stone's throw from there is a dining room with a table made out of raw wood imported from Venice, Italy, big enough to fit 10, and one that Chelsea loves to serve dinner in alongside her many Hollywood friends. Of course, if your dining room looks anything like that, then you better have a gourmet kitchen, and that's exactly what Chelsea has, as well as with an agate stone kitchen island and her go-to beverage maker of choice, an espresso machine. Then there's the den that features a glass chandelier that looks kind of like soap bubbles. Oh, and all those spaces I just mentioned? They open directly to the decks and patios for the ultimate in Southern California indoor-outdoor dining, just like Chelsea wanted. Elsewhere on the property are five guest bedrooms, one of which Chelsea has outfitted as a gym. Then there's her master suite, with a bedroom sitting area, TV built into the ceiling, an all-marble bathroom infused with a sauna and steam shower, as well as an extra-large dressing room. Other amenities include an upstairs terrace that overlooks the property's sloped backyard, which itself features a staircase that allows occupants to go up and down the hillside with ease, and is complemented with colorful plantings above a concrete retaining wall. There's also a dark-bottom swimming pool, which boasts a waterfall feature, along with a raised spa and an alfresco dining deck with full outdoor kitchen. After living here for eight years, Chelsea listed this property in 2018 for $11.5 million. When she didn't find a buyer, she pulled the home before relisting it in 2019 for $10.95 million. A couple of years later, she finally found someone willing to shell out $10.4 million, an announcement that Chelsea made in her typical style, sitting naked in her hot tub while smoking. Now, it wouldn't take her long to discover her next dream home, so let's take a look at that next. While criss-crossing North America on her Vaccinated & Horny World Tour, Chelsea Handler somehow found the time to seal the deal on the purchase of her newest property, located in Los Angeles' rustic and pricey Mandeville Canyon area. This relaxed and luxury spread sits at just under half an acre of land, and it's secured behind gates, as well as a gigantic hedge. Chelsea dropped $5.8 million on this new property in November 2021, taking ownership of the home from Curb Your Enthusiasm star Sheryl Hines. With just over 4,600 square feet of space, the main house has four ample-sized bedrooms, as well as four-and-a-half baths. But there's also an 850-square-foot semi-detached guest home, converted from a garage, that even has a laundry room, as well as a bedroom-bathroom combination. There's also a media lounge here that spills out into the backyard through a wall of French doors. Meanwhile, over in the main home, the formal living and dining rooms are complemented by a window-line study and a family room anchored by one of the home's three fireplaces. There's also a huge eat-in kitchen that's been arranged around a gigantic island and utilizes numerous top-of-the-line appliances, as well as some elegant grey and white checkerboard marble floors. Upstairs is, of course, the primary suite that features a ton of extra space, a small sitting area, as well as a tile-floored bathroom with dual vanities and light blue cabinets, as well as a deep-soaking tub for the ultimate in relaxation. As for the backyard, it's set into a steep, wooded hillside. As for the backyard, it's set into a steep, wooded hillside and boasts a terrace, as well as a huge stone patio with a fire pit and bar, plus a patch of fake grass and an eye-shaped spa that pours over a stone and tile edge into a swimming pool. All in all, it's a pretty gorgeous spot. And you can see why Chelsea considered upgrading from her already-glam former home. That being said, Chelsea also owns one more property she likes to keep more on the down-low, a gorgeous spot in Whistler, British Columbia, Canada. Chelsea Handler visited Whistler for the very first time about 10 years ago for her 38th birthday. After being blown away by the place, she'd spend the next three years visiting each year, along with a group of her closest friends to celebrate her special day. And a few years later, Chelsea became determined to teach herself how to get better at the sport. Soon after, she bought a piece of property in the area. And while we don't know exactly where it's located, or what it even looks like, we do know exactly why she did it. Writing for The Hollywood Reporter, Chelsea would say, I bought my house in Whistler on FaceTime before the 2020 election because I was so worried that Donald Trump was going to win again. And there was no chance I could suffer through another four years in this country if that were to happen. Trump might not have won, but Chelsea did keep her little cabin anyways. Now, she's turned it into a super cozy getaway that she escapes to as frequently as she can. But most importantly, it serves what she refers to as her three main passions in life. Reading books, smoking cannabis, and skiing. A typical day for Chelsea in Whistler goes a little something like this. She'll wake up early, get a Peloton abs class in, then be out the door by 9am. Since her cabin is skiing and ski out, she throws on a pair of skis and meets up with her friends. They'll eventually stop for a mid-morning drink, then ski more, followed by more drinking, and eating before margaritas cap the evening off. Following that, Chelsea is usually home by 7pm. That's when she hops in the bath with some Epsom salts to read a good book. Afterwards, she'll head to bed, and the next day, the routine begins all over again. Yep, sounds like quite the vacation to me. And if Chelsea had her way, she says that she'd spend every year between December and March living this exact way. Best of all, almost no one in Whistler ever recognizes Chelsea or bothers her while she's out buying her own groceries, something she just can't do in LA. But the one routine that basically everyone has come to expect out of Chelsea is her annual topless skiing video that she posts to social media in celebration of her birthday. Often accompanied by a margarita glass in one hand and a joint in the other, Chelsea likes to celebrate her American heritage, as well as her newly adopted home of Canada with a few strategically placed AC flags. I can't even imagine how cold that must feel, but it's so cool that Chelsea Handler has carved out a life for herself here in Canada, and for the fact that she's doing so on what is clearly her own terms. This just goes to show you how undeniable she's been throughout her entire career. Will Chelsea ever decide to move to Canada full-time, or will part of her heart always remain in Los Angeles? Well, we'll just have to wait and see. But for now, that'll bring this latest house tour to a close. Thanks so much for watching today's video. And before you head out, consider answering the following question. If you could buy a home in any country besides the one you were born in, which would it be? Since I'm in Canada, I would pick the States, but I don't know where. Somewhere in the mountains or Vegas. Anyways, let me know if you would be looking at a few warmer destinations than Canada in the comments below. Otherwise, like, subscribe, and turn on your notifications to make sure you never miss a drop. I'm Cara the Vampire Slayer. Follow me on Instagram to chat. And if you'd like to check out another tour before you're finished, then stay tuned for this one. It takes a look inside the home of one of Chelsea's closest friends, Jennifer Aniston. I'll see you all next time. Bye!