With her new memoir, The Woman in Me, which launched in October, Britney Spears is looking back on her life so far. And that has inspired us to look back at her life in real estate. Soon after Britney Spears’s debut album …Baby One More Time skyrocketed her to fame in the late 1990s, the pop star started investing in houses. For more than two decades now, the “Toxic” singer has been buying and selling homes for herself and her family. (When it comes to buying real estate, her mantra seems to be, “Oops, I Did It Again!”) In 1999, she custom-built a place for her parents in her hometown of Kentwood, Louisiana. Two years later, at 19 years old, she purchased her first major Los Angeles property. She once lived in an iconic New York City penthouse previously owned by the likes of Cher and Keith Richards. Currently, she resides in an Italian villa-style home on a 21-acre property in California that was originally developed by actors Sylvester Stallone and Bruce Willis.

And those are merely the news stories. We’ve listed every house the singer has had over her ground-breaking career below.

Britney constructs a house in Kentwood, Louisiana in 1999.

Britney’s mother’s house is the first and longest-held property she has owned. The pop singer purchased 7.4 acres of land in her birthplace of Kentwood, Louisiana, following the release of her debut album in 1999, and she constructed the approximately 6,500-square-foot house for her parents, according to property documents examined by The Wall Street Journal. Serenity is the name she gave the place, and she has been known to remain there when she comes. The tabloid stated that Britney “monitors the maintenance of the property and the expenses incurred for its maintenance,” citing court documents from a few years ago.

2001: Britney Buys a Hollywood Hills Estate

At the age of 19, Britney acquired her first significant property in Los Angeles, a home in the Hollywood Hills that she allegedly paid $2.95 million for. Rising Glen Road leads to the gated property, which offers views of the Sunset Strip. She received $3.85 million in 2003 when she sold the property to Brittany Murphy.

Spears and Murphy both mentioned feeling uneasy about the house, which begs the issue of whether it’s haunted. Julianne Kaye, Spears’s former makeup artist, told the account of her otherworldly encounter with malevolent spirits on an episode of the podcast We Need to Talk About Britney.

While Murphy didn’t report any ghostly occurrences, she always felt there was something off about the house. Her husband, Simon Monjack, told The Hollywood Reporter in 2010 that she hated the house and always wanted to stay at The Beverly Hills Hotel instead.

2002: Britney Purchases a New York City Penthouse

By 2002, Britney opened her first restaurant, Nyla, in New York City. Naturally, she put down roots there by purchasing a penthouse in Manhattan’s Noho neighborhood for a reported $3 million. Located in the famous Silk Building, the quadplex has been previously owned by other stars including Cher, Keith Richards, and Russell Simmons. Britney listed the place in 2004, and it eventually sold for $4 million in 2006.

2004: Britney Secures a Malibu Dream House

After marrying Kevin Federline in 2004, Britney purchased a Malibu mansion for just under $6.9 million, according to The Los Angeles Times. Located in the Serra Retreat neighborhood, the home boasts eight bedrooms and eight bathrooms across more than 9,000 square feet. The gated property was built in the ’80s and comes with plenty of amenities including a tennis court, pool, gardens, and outdoor kitchen. In 2006, Britney filed for divorce from Federline and placed the home on the market the following year. It sold for $10 million, according to the WSJ.

2007: Britney Moves Into a Beverly Hills Villa

After Britney and Federline’s marriage ended, she moved into a Beverly Hills villa. She paid $6.75 million for the Mediterranean-style house. The 7,800-square-foot home features a sophisticated lobby with a chandelier atop it, stone floors, and high ceilings. Britney was observed being carried from the house on a stretcher in 2008. After that, conservatorship was granted over her and her estate. According to the WSJ, the mansion sold for $4.25 million in 2012. Check out the house’s interior here.

2012: Britney Purchases a Westlake Village Home

After staying in rentals, Britney settled down in the suburbs with her two sons. She purchased a home in the Lake Sherwood area of Westlake Village, California, for an undisclosed amount, per property records reviewed by the WSJ. Built in 2010, the Mediterranean-style home is comprised of five bedrooms and seven bathrooms. Britney sold the home for $7 million in 2017.

2015: Britney Invests in a Thousand Oaks Estate

In 2015, Britney purchased another place in the Hidden Valley area. This time, she went for an Italian villa-style home located in Thousand Oaks, California. The 21-acre property—which she bought for $7.4 million—was originally developed by actors Sylvester Stallone and Bruce Willis. The nearly 12,500-square-foot home boasts 35-foot-tall ceilings, an oak-paneled library, a separate pool house with a kitchen, a 3,800-bottle wine cellar, a tennis court, an infinity pool, and even a three-hole golf course, according to Zillow. Currently, the home is estimated to be $10 million.

2022: Britney Buys a Calabasas Home

Shortly after her wedding with Sam Asghari, Britney purchased a Calabasas, California, home for $11.8 million. The seven-bedroom, nine-bathroom home encompasses 11,600 square feet. Her time at the contemporary Mediterranean-style estate was short-lived, as she sold it less than a year later for $10 million, which was $2 million less than her asking price. Britney and Sam then moved back into her Thousand Oaks home, where Britney now lives after they separated and Asghari filed for divorce. Details of the home’s open-plan living room (already decked out with a Christmas tree) and confusing kitchen can be seen in the dance videos the pop star posts.