For one of the world's biggest pop stars, Britney Spears' journey up the property ladder has been far from straightforward. Her life – and accumulation of wealth and houses – has been complicated by her much-discussed conservatorship. Now enjoying complete control over her finances, personal life and medical decisions, we go through the keyhole into the homes of the princess of pop. As she's reportedly back in her longtime home in Thousand Oaks, LA after flipping her new Calabasas home back onto the market, we ask: what went wrong? Click or scroll on for more...

On 12th November 2021, after nearly 14 years, Britney Spears' conservatorship finally came to an end after a Los Angeles judge terminated the court-ordered arrangement. The landmark ruling came after Britney spoke in court in June 2021, revealing just how much the arrangement controlled her life. In one particularly shocking report, it was revealed that she was unable to make basic decisions over things such as where she could go or how she could decorate her Thousand Oaks mansion. Now free from the conservatorship, Britney has been making moves on the property ladder – as well as buying (and selling?) a new estate in Calabasas, the star has also recently listed a Florida property she's had in her portfolio for 21 years.

With a net worth of approximately $60 million (£48.2m) – a sum that Forbes called "shockingly low" compared to contemporaries Jennifer Lopez and Jessica Simpson—the notoriously private star has worked her way through an incredible roster of real estate over the years, including a paparazzi-proof mansion in Beverly Hills and a stylish New York penthouse. But Britney wasn't born into such a palatial property. Starting from her modest childhood home in Kentwood, we look back through Britney's road to fame and peek inside the properties she's stayed in along the way...  

A world away from her life today, Britney Spears was born on 2 December 1981 in McComb, Mississippi. However, she spent most of her childhood in Kentwood, Louisiana alongside her brother, Bryan and sister Jamie Lynn. It was not long before she found her passion for singing and performing, destined for the stage from a young age.

At the age of eight, the budding singer went to audition for a role on Disney's the All-New Mickey Mouse Club but didn't land a part. However, just two years later, aged 10, she showcased her talents on Star Search, which gained her some public attention, though she ultimately did not win the competition. 

Britney and her family lived in this humble ranch-style home in Kentwood, Louisiana, where Britney spent most of her childhood until she was signed by Jive Records at just 15. Sitting on a two-acre lot, the house has three bedrooms and two-and-a-half bathrooms, which would have been perfect for the young family. 

This modest celebrity childhood home, which was previously on the market for $289,000 (£232k), is tucked away from the hustle and bustle of the town centre. It boasts a wood-panelled living room, two storage buildings and even a dance studio with mirrored walls, where we imagine Britney spent her days practicing.

Now the only empty room in the house, which came fully-furnished in the sale, is the star's former bedroom. The local unofficial Britney Spears Museum stripped it bare to recreate her bedroom layout, so that fans can come and see how the star lived before her meteoric rise to fame. 

Not long after appearing on Star Search, Britney auditioned a second time for the All-New Mickey Mouse Club, and got the part. She starred alongside other future stars such as Christina Aguilera, Justin Timberlake and Ryan Gosling for two seasons. 

After her time in the All-New Mickey Mouse Club came to an end in 1995, Britney started focusing on her singing career. She visited New York in 1997, and started auditioning for record labels, eventually getting signed by Jive Records. Immediately moving to New York, staying in one of the company's penthouses, she released her first single, '...Baby One More Time', in 1998. 

After the huge success of her first single and her debut album, which was released in January 1999 and sold 25 million copies worldwide, the star decided to splash out on a home just outside of Kentwood, Louisiana. Named Serenity, the custom-built property was home to Lynne Spears, Britney's mother. The star's estranged mother now reportedly still lives in the town in a $2 million (£1.6m) new build.

After hitting the big time, the star also snapped up this home in the celebrity property hotspot of the Hollywood Hills for $2.9 million (£2.4m).. Britney went on to sell the home to late actress Brittany Murphy in 2003 for $3.9 million (£3.1m). 

Since the star lived in the home, it's undergone extensive ground-up renovations and is unrecognisable. Located above Sunset Strip, it boasts five bedrooms and seven-and-a-half bathrooms, with sleek finishes throughout and floor-to-ceiling windows that look out over expansive city views. 

Britney was living in the home while dating Justin Timberlake, and it would have been the perfect place for the couple to hide away. Today, the high-end kitchen opens out onto the wooden planked patio deck, which is perfect for alfresco dining.

The huge 2,000-square-foot master suite with sweeping views of the city boasts two walk-in wardrobes, two ensuite bathrooms and a private patio. As well as all of this, the home features jaw-dropping amenities, including an elevator from the garage to the master bedroom, a wine cellar, a home theatre and an infinity pool and spa.

According to Realtor, Bridgemore Timber LLC, an entity owned by Britney purchased this palatial pad in Destin, Florida back in 2001 for $920,000 (£740k). Built in 1983, the waterfront retreat offers three bedrooms, four bathrooms, and stunning ocean views. 

The condo became a point of contention during the 2021 'Free Britney' movement, when a 2015 tweet by Britney's younger sister, Jamie Lynn, resurfaced, in which Lynn claimed that the condo was her favourite vacation spot. She tweeted: "We have a condo is [sic] Destin, Florida and it’s the best getaway”. Contrary to the indications of the rediscovered tweet, Jamie Lynn had previously claimed that she had received no financial support from Spears. Jamie Lynn later posted on Instagram that she owned no such residence, and no one had bought her a beach property. 

Housed in the prestigious Regency Towers in the northwest Floridian city of Destin, the penthouse encompasses half of the tenth floor and includes a spacious private deck overlooking the glittering ocean. The residence's stylish accommodation is spread across 3,648 square feet, so Britney would've had plenty of space to stretch out. 

A glamorous marble-floored foyer with 10-foot-high ceilings leads seamlessly into an open-floor living and dining area, offering 180-degree views of the ocean below. The living area also features a wood-burning fireplace and a wet bar, ideal for entertaining A-list guests. After owning the property for over 20 years the star put her glamorous condo in Florida's Panhandle on the market in September 2022 with Coldwell Banker for $2 million (£1.6m) and it sold for $2.2 million (£1.7m) in December 2022.

The luxurious master suite boasts floor-to-ceiling windows, a desk nook, balcony access and dual walk-in wardrobes. The master ensuite is equally decadent, with a spa-style soaking tub, walk-in shower and a bidet. To ensure guests enjoy plenty of pampering, the two junior suites also offer breathtaking ocean views, as well as their own oversized ensuites and walk-in wardrobes. We wonder who'll snap up the pop star's pad?

In 2002, before she sold her first ever Hollywood home, Britney purchased a prestigious penthouse in the trendy NoHo area of New York City for $3 million (£2.4m). Located in The Silk Building which has been home to the likes of Cher, Keith Richards and Tom Cruise, the property was listed in 2004 for $6 million (£4.8m), and finally sold in 2006 for $4 million (£3.2m). 

Spread over 4,400 square feet and four floors, the quadruplex penthouse has three bedrooms, five bathrooms and 13-foot-high ceilings. The airy, open-plan living and dining room (with a retro red leather banquet) and kitchen are located on the same floor. 

The three bedrooms are located on the lower two floors, while a solarium, wood-burning fireplaces and a rooftop terrace with downtown views are just a few of the jaw-dropping amenities that Britney would have utilised while she was spending time in the Big Apple.

Built around 1908 and converted in 1983, this famous loft in the heart of Greenwich Village is the perfect fit for a young A-lister. The fully-serviced historic property offers a 24-hour doorman, a roof deck and a stunning lobby. Talk about luxury! 

After releasing her fourth successful album, In the Zone, in 2003, Britney went on to marry Kevin Federline in September 2004. The couple soon snapped up this property as their marital home the same year for a reported $13.5 million (£10.9m). They went on to sell the home for $10 million (£8m) in August 2007 after they divorced. 

Located in Malibu's Serra Retreat, the home has since undergone renovations by the new owner. Boasting vaulted two-storey ceilings with an open floor plan, the grand hallway opens out onto the magnificent garden, making it perfect for seamless indoor-outdoor living. 

The lavish master suite sits alongside five more bedrooms and features an amazing attached personal gym, a marble bathroom with a steam shower and twin walk-in wardrobes. 

The home isn't short of lavish amenities, with a children's playroom, movie theatre, office and a large den. Heading outside, the garden has panoramic views over the estate, and a relaxing waterfall yoga area, a custom pool and an in-pool bar.

Fresh from her divorce with Kevin Federline and in the midst of a child custody battle – as well as working on a comeback tour – 2007 was a tough year for Britney as she experienced an incredibly public breakdown. However, in November of that year she purchased this private home in the Summit area of Beverly Hills for $6.8 million (£5.5m). 

The Mediterranean-inspired villa offered Britney the privacy she needed during a troubled time in her life, and has been dubbed 'paparazzi proof'. The fortress-like home sits within a gated community, and is spread over 7,500 square feet with soaring ceilings, stone floors and a glittering chandelier in the expansive hallway.  

Seven bathrooms sit alongside six bedrooms, which include the master suite with a grand fireplace and private balcony. Elsewhere there's a large family room, chef's kitchen, theatre and separate maid's quarters: the perfect home for a private pop princess!

Each of the rooms on the lower floor opens up to the backyard, which comes complete with lush landscaping, manicured gardens, custom swimming pool and firepit. Britney put the home on the market in both 2008 and 2010, eventually selling at a loss in 2012 for $4.3 million (£3.5m).

The pop star moved into this Calabasas home in 2009 with her two sons after struggles with her mental health the previous year. Then, with all her money under a conservatorship with her father, she reportedly rented with an option to buy, and invested more than $700,000 (£563k) into upgrading the home. 

Located in an area also home to the Kardashian family, the 10,500-square-foot French chateau-style manse has six bedrooms and seven bathrooms. Designed around an interior courtyard with an antique limestone fountain, the interiors are grand and opulent, with soaring ceilings and polished hardwood floors. 

Further inside the home, the bright white country kitchen sits alongside a two-storey library tower with a private office, bar and fireplace lined with wood-panelled bookshelves. 

Amenities include an elevator, wine cellar, a library and maid's quarter and a subterranean garage equipped with two hydraulic car lifts. The estate is spread over an acre of land and includes a stunning glass mosaic swimming pool. After moving away from Calabasas, the star rented out another mansion in Thousand Oaks in 2011.

In 2012, with her career back on track once more, Britney decided to invest in this home in the Thousand Oaks area, not far from where she had been renting. The star reportedly purchased the home for $6.8 million (£5.5m), before selling it in 2017 for $7 million (£5.6m), during the last year of her sell-out Las Vegas residency. 

The single-storey home was built in 2010 and sits on one-and-a-half acres of land within the guarded gates of the prestigious Sherwood Country Club. Inside, the double-height grand foyer leads through to the formal living room, which boasts brown oak floors, exposed beam ceilings and a striking black marble fireplace.

The five-bed, seven-bath home also boasts a media room, which sits just off the comfortable family room and an open kitchen with two central islands. 

Outside, the modern Spanish-style estate sits in elegant grounds which are made up of two parcels of land. With sprawling views over the Santa Monica mountains, the swimming pool is the perfect spot to enjoy the Californian sun. 

In 2015, Britney rewarded herself with this amazing estate, also in Thousand Oaks, which she purchased for $7.4 million (£6m). The palatial Italian-style villa has 13,300 square feet of space and sits in the heart of Los Angeles, with views over the skyline and 20 sprawling acres of private land. 

The entrance is just as grand as the exterior with marbled floor, huge pillars and impressive tall windows. It leads through to the main living space, which features 35-foot high ceilings, a large fireplace and a grand staircase that leads up to the second floor, where you'll find five bedrooms and seven-and-a-half bathrooms.

The huge kitchen boasts a centre island and dark wooden cupboards in a country style. Further into the home is a formal living room and wood-panelled office, as well as a media room and a 3,500-bottle temperature-controlled wine room. 

Post-conservatorship, the kitchen became a topic of conversation. The New York Times reported that the star "expressed serious opposition to the conservatorship earlier and more often than had previously been known, and said that it restricted everything from whom she dated to the color of her kitchen cabinets".

The manicured grounds, which often appear on Britney's social media, also house a poolside pavilion with its own kitchen and bathroom and panoramic views over the mountains. Further into the grounds sit a lit tennis court, an orchard and a three-green golf course.

Fitness fanatic Britney often shows off her gymnastic skills with images from her home gym, which is decked out with mirrored walls and top-of-the-range equipment. However, in April 2020, she revealed she'd accidentally burnt down part of her gym in a fire, and only had two pieces of equipment left!

Regularly sharing pictures from her life on Instagram, the star is often seen trying out new looks as well as her infamous dance moves in her spacious hallway. This outfit is one of the star's more conservative looks!

Britney Spears married her long-term partner, Sam Asghari on 9 June 2022 at her Thousand Oaks home. Having met the actor and fitness expert on the set of her ‘Slumber Party’ music video in October 2016, according to Vogue, Britney reportedly found his number in her bag and decided to give him a call. Making their relationship official on New Year’s Day 2017, Sam ended up proposing in September 2021 with a custom diamond ring by Roman Malayev, featuring an engraving of her nickname, Lioness. Newly freed from her conservatorship, the star was keen to marry her beau...

The wedding had a beautiful floral theme, with displays of blush, cream, pink and red florals matching the event’s warm colour palette. The pair planned their wedding with celebrity event producer Jeffrey Best of Best Events, according to Vogue, with the 'Lucky' star expressing her desire for a "small and beautiful moment with family and friends". While members of her family were notably absent, guests included a glittering line-up of VIPs including Madonna, Selena Gomez, Drew Barrymore, Paris Hilton and Donatella Versace.

As reported by the BBC, a controversial wedding crasher arrived unannounced in the form of Britney's ex-husband Jason Alexander, but the celebrations, thankfully, continued without a hitch. Ever the performer, Britney changed into three different looks by Versace for the party. While the newlyweds reportedly didn’t have a formal first dance, Selena Gomez, Madonna and Britney danced to 'Toxic' before Paris and Britney were said to have sung 'Stars Are Blind' together. At a modest 10:15 pm, the bride and groom left in a Rolls Royce while their A-Lister guests continued to dance late into the evening.

After tying the knot – and, according to TMZ, signing an "ironclad prenup" – the loved-up newlyweds began swiftly moving into their huge new mansion, with removal trucks seen outside the mansion on Monday 13th June 2022, just four days after their wedding. The 11,650-square-foot abode was snapped up by Britney for $11.8 million (£9.5m), as first reported by TMZ, and resides within the celebrity-favourite neighbourhood of Calabasas, near the city of Los Angeles. 

Built in 2008, the six-bedroom, nine-bathroom manse sits on 1.6 acres of land and can be found nearby Britney’s ex-husband Kevin Federline’s home, where he lives with their two teenage sons Sean, 17, and Jayden, 16. 

With ornate tiled flooring and vaulted marble ceiling, the master bathroom is something to behold. A large chandelier hangs decadently above the plush seating area and marble bath, framed with columns and inset paintings. The dual mirrored dressing areas are the ultimate his-and-her sinks for a glamorous couple.

Set behind the second security gates in the highly desirable Estates at The Oaks, the house is extra secure with custom entry steel doors and both indoor and outdoor security cameras for added peace of mind. However, it seems Britney didn't warm to the new pad...

However, just six months after moving in, the newlyweds reportedly put their new Calabasas home back on the market, priced at $12 million (£9.9m). Dirt reported on 28 February 2023 that she has accepted an offer of $10.1 million (£8.4m). That's $1.7 million (£1.4m) less than she purchased it last summer. Britney had continued to post content from their old Thousand Oaks home, even after moving into their new residence – as seen here in a still from an Instagram video. Could it be something to do with Britney’s ex-partner, Kevin Federline being a close neighbour? Britney and Kevin are said to be "not on good terms" and she is reportedly terrified of what he may reveal in his upcoming book about fatherhood. 

According to The Mirror, the Toxic singer just hadn’t "fallen in love with the new home". A source close to the couple reportedly told HollywoodLife that Britney “always preferred" her old house. “It is simply that Britney feels safe in her Thousand Oaks house, and she has so many memories there." According to the source, Britney "never really vibed with the new house." However, they denied that it was anything to do with the Calabasas location of the house and its proximity to her ex. 

It was reported recently that Britney hasn't seen her sons, Sean, 17, and Jayden, 16, for several months due to their "complicated relationship", as described by the boys themselves in an ITV News interview. In the interview, Jayden optimistically stated: "I 100% think this can be fixed. It's just going to take a lot of time and effort." 

Britney is marking a year and a half since her conservatorship ended in November 2021. After deciding to offload what was supposed to be her newlywed love nest and remain in her old Thousand Oaks home with her new husband, fans may have hoped Britney had finally found some stability. However, a new documentary has thrown that into question. TMZ's Britney Spears: The Price of Freedom, which aired in the US on 15 May, has made shocking claims that she lives in "virtual isolation" from the outside world.

The documentary claims that Britney spends her time "tanning by the pool, reading fiction and driving aimlessly around her neighbourhood", as well as posting solo dancing videos to Instagram. It is also alleged that the superstar drinks so many caffeinated drinks that she sometimes stays awake for days at a time. However, Britney brushed off the claims. Addressing the reports via Instagram, she said although "green tea is my prized possession", she never stays up late with Red Bull, saying "it is absolutely the worst drink ever". The Price of Freedom also dropped bombshell allegations concerning the pop princess' relationship with new husband Sam Asghari... 

The doc reported that the pair have "screaming arguments" and even made allegations that Britney posed a physical threat to her husband. However, the couple continues to display their love in affectionate social media posts, including this one, in which Britney revealed that the pair are redesigning their home. "Ok so I’m proud of my flowers!!!" she wrote in the caption. "I’ve been pretty modest about my home!!! I’m redesigning my house!!! I feel so blessed to be with such an incredible husband who inspires me everyday."

Sam took to Instagram to refute the claims, saying in a story that, although he didn't want to speak on his wife's behalf, he "found it absolutely disgusting" that people who were in Britney's life at the time when she didn’t have a voice subsequently "told her story like it was theirs". He also posted a video of the couple enjoying a seaside hike together on 12 May, captioning the post "Hike with my woman," perhaps in an attempt to pour water on the negative rumours surrounding their relationship. 

In more bad news for Britney, it has been reported that her sons Preston and Jayden may be moving to Hawaii, a five-and-a-half-hour plane ride away. TMZ claims the singer hasn't seen her children in over a year – since before her marriage to Asghari – and alleges that their father, Kevin Federline, and his lawyer have sent the songstress a letter asking if she would allow them to "relocate to Hawaii full-time." If she objects, TMZ's sources say Federline is prepared to go to court. If they do move to Hawaii, it wouldn't surprise us to see Britney buying a Pacific island pied-à-terre in the very near future...

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