Moonwalking In Calabasas: A History Of Larger Than Life Homes In California's Most Exclusive Gated Community

The city of Calabasas, California is known as one of the most exclusive communities for American celebrities in the entire country. Drake has rapped about it on numerous occasions, most notably in "4 PM in Calabasas" from 2016. The Kardashian clan also calls this city their home, and most recently, rapper Kanye West has given the gated community new publicity in interviews, such as his 2019 sit-down with Charlemagne Tha God.

Calabasas is a city in Los Angeles County, California known for being the home of famous rappers such as Drake, Kanye West and Dr. Dre among others. It is an exclusive neighborhood where celebrities such as the Kardashians live and its population of 23,853 makes it a quaint and sheltered community where the rich rule the roost.

Calabasas is a suburb of Los Angeles and is much quieter than the busy city. Most of Keeping Up With the Kardashians was filmed there and was the first show to really shed light on the area. While it is known as a hub for rappers, stars like Selena Gomez, Miley Cyrus, and Justin Bieber have all lived here at one time or another.

What Are The Benefits of Living in Calabasas?

The main benefits of Calabasas come in its safety. Rich celebrities seek to escape the hustle and bustle of the busy city by coming to the gated community of Calabasas. What is a "gated community"?

A gated community is a private neighborhood that restricts access from pedestrians, bicycles and automobiles. Identification is required for entrance and the community is often walled or fenced in to prevent interlopers from entering.

As you can see, being a celebrity can force you to rethink your surroundings, and so, to get away from all the fans and paparazzi, a house-hunting trip to Calabasas can seem like a pretty good idea. This is especially important if you are raising children in southern California.

Khloe Kardashian, Kylie Jenner, and Kourtney Kardashian all call this area home. They are all choosing to raise their children in the safe city of Calabasas. Another benefit for them is that their mother Kris Jenner is just up the street whenever they need her for babysitting.

Calabasas is also known for a few of its excellent perks. For instance, it has one of the best school systems in the area and also its own private fire department. When you are a celebrity who takes pride in the finer things, Calabasas is the place for you.

Which Celebrities Live In Calabasas?

Many different types of celebrities call Calabasas home. Rappers and entertainers alike join together to form this cozy community. Which celebrities live in Calabasas?

Many different celebrities live in Calabasas including Kim Kardashian, Khloe Kardashian, Kourtney Kardashian, Kris Jenner, Kanye West, Drake, French Montana, Iggy Azalea, Justin Bieber, Miley Cyrus, The Weeknd, Will Smith, and Jessica Simpson.

While the celebrities in Calabasas make up a unique cast, some have bigger homes than others. Homes in Calabasas have the nice tendency to increase in value over time, which makes each custom home a major investment opportunity as well.

Who Has the Most Expensive Home In Calabasas?

While all the houses and mansions in Calabasas are breathtaking and enormous, some outshine the others. We are going to count down some of the biggest and most beautiful properties in the Calabasas area.

1. Will Smith, Jada Pinkett-Smith, and Family, $42 Million 

Although the power couple has had much-publicized trouble in recent times, they still have one of the largest homes in the state of California. The Smith family has more of a resort than a home. Their 25,000 foot home sits on 150 acres of land and has many amenities. They have a basketball court, a tennis court, a volleyball court, and a massive pool.

There is even a lake with its own private gazebo, perfect for taking in nature and relaxing. Purchased in 2003, the home took over 7 years to complete. The Smiths bought this home for their children Willow and Jaden to grow up in.

2. Drake, $7.7 Million

Drake calls this spot his YOLO Estate. "This house was the desktop image on my computer years before I bought it," he said. Drake's favorite part about the house? The giant pool of course.

While speaking with Rolling Stone, he said, "One of my goals in life is to have the biggest residential pool on the planet." Well, he is coming pretty close to checking that one off the list. Drake's Calabasas home has a tennis and basketball court, a recording studio, a massive theater and screening room, and even a mechanical bull.

3. The Weeknd, $20 Million

Legendary crooner Abel Tesfaye, also known as The Weeknd, has one of the most impressive homes in all of Calabasas. His home has 12,000 square feet of space, including 9 bedrooms and 11 bathrooms.

Amenities include a deluxe pool and spa, a wine cellar, home theater, music lounge, and a large gym as well. Abel purchased his home in 2017 and owns one of the most expensive homes in the area.

4. Kourtney Kardashian, $8.5 Million

Kourtney is just one of many Kardashians in Calabasas. With that in mind, know that Kourtney has one of the nicest houses in the area. She lives here with her three children. She is only a couple of minutes away from sister Khloe Kardashian and a short walk from Kim.

Kourtney's home is 12,000 square feet and features 6 bedrooms and 7.5 bathrooms. Amenities include a huge pool, an incredible gourmet kitchen and a spa room as well. 

5. Kris Jenner, $10 Million

Although Kris has a $4 million home that she shared with her ex-husband, she now has a 9,400 square foot home which she purchased in 2017. The amenities are numerous and it includes 6 bedrooms and 8 bathrooms.

The move to Kris' second home in 2017 was mostly to perform her grandmother duties to Kim and Kanye's children. In fact, this home is direct across the street from Kim and Kanye.

6. Kim Kardashian and Kanye West, $60 Million

Perhaps the most noteworthy members of the exclusive Hidden Hills gated community inside of Calabasas are Kim Kardashian and Kanye West. Although they have recently announced their divorce, the home they once shared is colossal and sprawls out on a massive space.

The home is modeled on french country homes and is an insane 15,667 square feet. It features 8 bedrooms, 8 bathrooms, along with two half-baths. It is unclear what the future of this home will be given the divorce, but one can assume it will make their $2.1 billion divorce case a tad complicated.

7. Kylie Jenner, $12 Million

Kylie has built her makeup empire from the ground up, and she rewarded herself with a 13,200 square foot home. It includes 8 bedrooms and 11 bathrooms. She has plenty of space to play with her daughter Stormi in the extremely large pad.

Kylie's impressive home has tons of amenities including a wine cellar, a game room, a gigantic pool, and even a home theater and viewing room. Kim is just up the way, and they and their children spend lots of time together in Calabasas.

8. Khloe Kardashian, $7 Million

Although Khloe lives in this large estate now, it previously belonged to Justin Bieber. He sold it to her in 2014, taking in a nice profit due to the value of land in Calabasas. Khloe lives here with her daughter True in a gated community known as The Oaks.

Khloe's home is derived from Spanish-style estates and features a swimming pool with a spa as well as a hair salon and personal dressing room. The home is 9,214 square feet and has 6 bedrooms and 7 bathrooms. 

9. Scott Disick, $3.2 Million

Even though Scott Disick and Kourtney Kardashian are no longer together, he still wanted to be in close proximity to her and their three children. With that in mind, he bought a house just down the street from her for $3.2 million.

Inspired by the Hamptons, Scott's mighty castle is more like a luxury hotel than a house. Boasting 5 bedrooms and 6 bathrooms, it has more than enough room for he and his kids to visit in.

10. Jessica Simpson, $11.5 Million

Similar to most residents of Calabasas, Jessica Simpson's awesome home is pretty pricey. She and her husband, Eric Johnson, bought the home from Ozzy Osbourne and Sharon Osbourne for a cool $11.5 million.

The home is palatial and features a senate-like dome and many-windowed facades. Amenities abound with a movie theater, a beautiful pool and spa combo, and a large garden area. It even has a guest apartment for total privacy.

11. Iggy Azalea, $5.2 Million

The "Fancy" artist who has a son with Playboi Carti just moved into this home. She is already planning some renovations of her own and she has lots of room to work with given the 3,982 square foot space. 

Iggy's beautiful home has four bedrooms and four bathrooms, as well as a 1,246 square foot guest house. She is currently planning to build a new playground and zip-line on the property as well.

12. Travis Barker, $9.5 Million

Eclectic drummer Travis Barker is well-known for his musical skills, but he is also one of the premier homeowners in the Calabasas area. His massive manor is almost 10,000 square feet and features amenities galore.

With a large enclosed pool and a walled-off courtyard, the home is picturesque. The home is cordoned off from the rest giving it some nice privacy.

13. French Montana, $3.3 Million

Rapper French Montana has quite a large home in this gated community. He paid $3.3 million for it and it is 7,700 square feet. Ironically enough, he lives pretty close to ex-girlfriend Khloe Kardashian, so one must wonder if that is awkward or not.

Although the amenities are pretty standard when it comes to celebrity mega-mansions, there are some pretty cool aspects to this home. He has a deluxe brick pizza oven, a gourmet kitchen, a large well-lit pool, and even a home theater for when he invites his famous friends over.

14. Katie Holmes, $3.79 Million

After her well-publicized divorce from Tom Cruise, Katie purchased this home for her and her daughter. The mansion has 6 bedrooms and 6.5 bathrooms with a fancy kitchen, spa, and athletic court, as well as a huge pool.

Katie lives here with her daughter Suri. Although normal people like us couldn't imagine ever leaving this paradise, Katie is actually selling her home. She currently has it listed for $4.6 million and may soon be out of Calabasas altogether. One can only imagine she will have an even nicer home wherever she lands.

15. LeAnn Rimes & Eddie Cibrian

Country superstar LeAnn Rimes lives in Calabasas with her actor husband Eddie Cibrian in a large estate. She is neighbors with both Kim Kardashian and the Smith family.

They purchased the home in 2006. It has 6 bedrooms with 9 bathrooms and 2 acres of land. In addition, it also has 8,642 square feet and a swimming pool, a guest house, and a huge four-car garage.

16. Rebecca Romijn and Jerry O'Connell, $1.325 Million

Two notable Calabasas residents include actor super couple Rebecca Romijn and Jerry O'Connell. They live here together with their twin daughters, Dolly and Charlie. Although she purchased this home with her ex-husband John Stamos in 2000, she actually married Jerry O'Connell here in 2007.

As you can see, Rebecca is just like anyone else, she needs to grab her own mail too. All kidding aside, this house is anything but normal. Amenities include a large garden with a poolside view.

Calabasas is the Place to be

As you can see, Calabasas is the ultimate home for an aspiring celebrity superstar. Rapper DDG, speaks about his #goals when he discusses how he would like to live and dance in Calabasas.

I recently purchased my first home last year, and although it is extremely nice in my opinion, I can't help but be kind of shocked at the level of luxury shown in these Calabasas' homes.

On one hand, not having any neighbors would be cool, because privacy is important, especially if you are a celebrity. For me though, I do enjoy living in a neighborhood where people are outside, enjoying the weather, having a barbecue, and waving to you from across the street. 

On the other hand, as a celebrity, you do have to consider things differently. It is not easy to understand what it is like to be a celebrity unless you have lived through it. Either way, I'm sure it has its ups and downs just like any normal life. 

Regardless, if being a celebrity is your dream, then Calabasas is the destination. If that is you, then good luck and take some inspiration from this list of the most expensive homes in Calabasas!