Last month, Britney Spears spoke out against the 13-year conservatorship that gives her father, James Spears, control over her finances. The pop star’s legal battle sheds light on her $50 million-plus fortune including one corner of her assets: her real-estate portfolio.

Ms. Spears, 39, was one of the most successful pop stars of the 1990s and 2000s, during which time she bought and sold several properties for herself and family members, according to property records. While she held on to some properties for as little as two years, others she kept for more than a decade.

One of her longest-held purchases is in her hometown of Kentwood, La. In 1999, the year her debut album was released, Ms. Spears purchased roughly 7.4 acres of land and built a 6,500-square-foot home for her parents, according to property records. Her mother still lives there, according to documents filed in Los Angeles County Superior Court.

Other homes came and went more quickly. In 2001, when she was 19, Ms. Spears purchased a 6,300-square-foot home in the Hollywood Hills of Los Angeles, according to records. She sold it two years later for $3.85 million to actress Brittany Murphy, who died in 2009.

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While not all purchase prices are known, some of the transactions were hit and miss. In 2007, records show Ms. Spears sold a home in Malibu for roughly $3.7 million more than she paid three years prior. In 2012, she sold a Beverly Hills villa for a roughly $2.5 million loss after the market collapsed during the financial crisis.

A summary of Ms. Spears’s finances, filed with the Superior Court, indicates she pays expenses for five residential properties, as of October 2020. Total expenses for those properties topped $979,000 in 2019, documents show. Although the document is redacted, the financial summary lists the home in Kentwood, as well as a $50,000-a-month rental in Los Angeles.

Representatives for James Spears, Lynne Spears and the conservatorship didn’t respond to requests for comment.

Read on for a closer look at some of Ms. Spears’s homes over the years.

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James Spears, Britney Spears’s father, recently sold the house she grew up in.

Kentwood, La.

Listed: $289,000 in June 2020

Sold: $275,000 in February 2021

Ms. Spears didn’t own her childhood home. James Spears recently sold the house she grew up in, according to public records. The property sits on 1.87 acres in the tiny Louisiana town best known for its connection to the pop star.

The roughly 2,300-square-foot house has three bedrooms and three baths, and a metal building that can be used as a dance studio or office, according to Zillow. (The Kentwood Historical & Cultural Arts Museum has a replica of Ms. Spears’s childhood bedroom.)

Ms. Spears’s mother lives in this Kentwood home.

Kentwood, La.

Paid: $29,362 in 1999

The year Ms. Spears’s “Baby One More Time” album made its debut, property records show she purchased a roughly 7.4-acre lot and built “Serenity,” a roughly 6,500-square-foot home where her mother lives, according to documents filed last year in Los Angeles County Superior Court. The documents indicate Ms. Spears stays there from time to time. She also “monitors the maintenance of the property and the expenses incurred for its maintenance.” The current value of the home couldn’t be determined.

Ms. Spears was 19 when she bought this Hollywood Hills home.

Los Angeles

Sold: $3.85 million in 2003

The pop star was 19 when she purchased this Hollywood Hills home via a shell company, Coastal Operatives, according to property records. The 2001 purchase price could not be determined. The gated property, which is 0.43 acres, is at the end of a steep driveway and has views of the Sunset Strip, according to Realtor.com. (News Corp, owner of The Wall Street Journal, also operates Realtor.com under license from the National Association of Realtors.) After two years, Ms. Spears sold the house to Ms. Murphy. The house was later renovated, according to building permits in the city of Los Angeles, and it now has an elevator, wine cellar and indoor-outdoor living spaces, according to Zillow.

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For a time Ms. Spears owned two units in this New York building.

New York City

Listed: Two-bedroom listed for $1.545M in 2011; penthouse listed for $6 million in 2004

Sold: Two-bedroom for $1.48 million in 2011; penthouse for $4 million in 2006

In 2000, Ms. Spears purchased a two-bedroom condo at the Silk Building in Greenwich Village and then bought a four-floor penthouse two years later, property records show. The purchase prices could not be determined.

Built in the early 1900s, the building was converted to condos in the 1980s and has 55 units. The penthouse measures 4,400 square feet and has five bedrooms and 4½ bathrooms with a chef’s kitchen, wood-burning fireplace and private terrace, according to a listing for the apartment, which is currently on the market for $6.8 million. When Ms. Spears owned the quadplex, it had a full-floor primary suite with a mini bar and private entry door, said Oren Shalev of Anchor Associates, who represents the current owner. The penthouse has been on and off the market since 2008, according to StreetEasy.

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Ms. Spears owned this Malibu home when she was married to Kevin

Malibu, Calif.

Paid: $6.3 million in 2004

Listed: $13.5 million in January 2007

Sold: $10 million in August 2007

After marrying Kevin Federline, Ms. Spears bought a 9,130-square-foot home in Malibu via a shell company named Love Shack Trust in 2004, according to property records. The roughly 1½-acre property is located in the Serra Retreat neighborhood, a private enclave that is home to a retreat center run by Franciscan friars.

In 2006, Ms. Spears filed for divorce from Mr. Federline, with whom she has two sons. She sold the Malibu home the following year for $10 million, a $3.7 million gain in three years, property records show. The eight-bedroom home was later rebuilt with a theater, waterfall yoga area and custom pool, according to Zillow. Property records show it traded for $11.45 million in 2014.

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She owned this Beverly Hills home between 2006 and 2012.

Los Angeles

Paid: $6.75 million in 2006

Listed: $5.495 million in 2010

Sold: $4.25 million in 2012

After her marriage to Mr. Federline, Ms. Spears purchased a Beverly Hills villa. Located in a gated community, the Mediterranean-style house is roughly 7,400 square feet with six bedrooms and seven bathrooms, according to Zillow.

In 2008, Ms. Spears was photographed being wheeled from the house in a stretcher, and a Superior Court placed her and her estate under conservatorship, naming her father as co-conservator of her estate. Ms. Spears sold the house for $4.25 million, according to Nancy Sanborn, an agent hired by the conservator. (In California, the sale of real estate under conservatorship must have court approval.)

That is roughly $2.5 million less than she paid. “She took a pretty big loss on it when she sold it,” said George Kahwaji of Rodeo Realty, who wasn’t involved in the 2012 deal but listed the property in 2018 for $9.45 million. (After an agent swap, the house traded for $6.1 million this year.) Mr. Kahwaji said Ms. Spears may have overpaid “slightly,” but her timing was also off due to the financial crisis.

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The pop star purchased this home in the Lake Sherwood area of Westlake Village in 2012.

Los Angeles

Listed: $7.995 million in 2016

Sold: $7 million in 2017

While under conservatorship, Ms. Spears purchased a roughly 8,400-square-foot estate in the Lake Sherwood area of Westlake Village in 2012. She bought the home from retired hockey player Russ Courtnall and his wife Paris Vaughan for an undisclosed amount, according to property records. (The house was listed for $8.5 million.)

Built in 2010, the contemporary, Mediterranean-style home has five bedrooms and seven bathrooms and sits on 1.42 acres, according to Zillow. It has a tile roof, arched doors and vaulted ceilings, along with a movie room, five fireplaces and three bedroom wings, according to a listing description on Zillow. Property records show a trust in Ms. Spears’s name sold the home for $7 million in 2017.

 

She bought this property in the White Stallion Ranch area, which was developed by actor and director Sylvester Stallone, in 2015.

Los Angeles

Bought: $7.4 million in 2015

Current estimated value: $10 million

In 2015, Ms. Spears purchased a $7.4 million estate in an area of Westlake Village called Hidden Valley, property records show. The 21-acre property is located in the White Stallion Ranch area, which was developed by actor and director Sylvester Stallone. The area is known for privacy, according to Nicole Van Parys of Engels and Volkers, who represented the home’s prior owner and estimates the home would be worth north of $10 million today.

Ms. Spears’s Italian Villa is roughly 12,500 square feet, property records show. “The way it is situated on the lot, you can’t see in and you can’t see out,” said Ms. Van Parys.

The home features a two-story entryway and 35-foot library ceiling. There is also a game room, detached pool house with a full kitchen, a 3,800-bottle wine cellar, tennis court, infinity pool, orchard and three-hole golf course, according to Zillow.