Trump’s Treasury Pick Has Bought and Sold at Least 20 Homes. On Some, He Lost Millions.

Hedge-fund manager Scott Bessent—Donald Trump’s pick to lead the Treasury Department—owns a piece of banking history: a pink-stucco building in Charleston, S.C., that housed a branch of the First Bank of the U.S. in the 1790s.

Bessent paid $2.6 million for the historic building in 2020, the same year he moved to Charleston with his husband, former New York City prosecutor John Freeman. Now, the three-story structure serves as Bessent’s Charleston office as well as the nerve center of his personal real-estate portfolio, a vast and ever-changing network of homes up and down the East Coast.

Since the 1990s, Bessent has bought and sold more than $127 million worth of U.S. real estate, including at least 20 properties in his native South Carolina, New York, Florida and elsewhere. Bessent, 62, has a penchant for historic homes, often restoring and living in the properties he buys. In Manhattan, he has lived in storied prewar buildings such as the Dakota, 1 Sutton Place South and 720 Park Avenue. His other purchases have ranged from a beach house in Provincetown, Mass., to a country home in the North Carolina mountains. Bessent also has a home in London and owns property in Lyford Cay, a private community in the Bahamas. If confirmed, Bessent plans to live in the Washington, D.C., area, according to a person with knowledge of his thinking.

Investment-wise, the results have been mixed. Bessent lost money on at least eight of the homes he has sold over the years, according to a Wall Street Journal analysis of property records. In 2012, for example, he took a $4.2 million loss on an estate in New York’s Westchester County, which he bought for $11.3 million in 2007.

In 2014, however, he sold a 1930s mansion in Miami Beach, Fla., for $14.5 million after having paid $9.5 million for it in 2010. And in one of his largest transactions to date, Bessent sold a circa-1880s Hamptons mansion for $19 million in 2019 after buying it for $9.95 million in 2012. But having spent millions restoring the home, it is unclear whether he made a profit. People familiar with Bessent’s thinking said he doesn’t view historic restorations as a pure investment. He makes a point of hiring local artisans and craftsmen, they said, and chooses properties for their historical significance.

A onetime top investor for billionaire George Soros, Bessent has said in speeches that he grew up in a small fishing village not far from Myrtle Beach, and that his father went bankrupt because of bad real-estate investments. “I’ve known financial anxiety and I do not want that for any family,” he said last month on Roger Stone’s radio show.

At Yale University in the 1980s, Bessent studied political science and economics and considered going into computer science and journalism, but chose finance instead. In 1991, he joined Soros Fund Management, where he ran the London office. Bessent was a driving force behind the firm’s bet that the British pound would collapse after he spotted marked weakness in the U.K. housing market. The firm netted more than $1 billion on the wager in 1992.

Bessent ran his own New York-based hedge-fund, Bessent Capital, from 2000 to 2005. Later, he taught economics at Yale, and after a stint at Protégé Partners, a New York-based fund of funds, he rejoined Soros as chief investment officer from 2011 to 2015. In 2016, he started Key Square Group—a firm named after a spot on the chessboard—that specializes in macro investing. He and Freeman married in 2011 and have two children.

Bessent’s affinity for historic properties stretches back decades. One of his early purchases, in 2006, was an 18th-century Charleston home. During Covid, Bessent funded the interior renovation of the French Huguenot Church of Charleston, a Gothic Revival structure from 1845. Bessent is a member of the church, and his relatives were founding members in the 1680s.

He has also served on the board of the Middleton Place Foundation, a nonprofit that owns a historic home and former plantation in Charleston. And he is a trustee of the Richard Hampton Jenrette Foundation, started by a fellow financier who collected historic mansions. In 2019, Bessent told The Post and Courier newspaper that the “glory” of Charleston was “the mosaic of time and the varying conditions of the houses on the peninsula.”

“I don’t remember Scott ever formally studying history, but he was always interested in it,” said Tracey Todd, a friend of Bessent’s and former CEO of the Middleton Place Foundation.

Bessent and Freeman have restored several properties in Charleston, including a circa-1840s mansion overlooking Charleston Harbor that received a local preservation award in 2021. The couple lived in the house for several years before listing it for $22.25 million in October, just weeks before Bessent got the Treasury nod.

“They did extensive research on the property to really fine-tune this thing and bring it back to what it once was,” said Robertson Allen of the Cassina Group, one of the listing agents. The listing is the priciest in Charleston, where Bessent and Freeman are looking to downsize, according to people familiar with their plans.

Here’s a closer look at some of the properties Bessent has bought and sold over the years.

DuBose Heyward House | Charleston, S.C.

Bought: $3.7 million in 2006

Sold: $3.6 million in 2007

In 2006—the year after he closed Bessent Capital—Bessent bought a circa-1790 house in the heart of Charleston’s historic district. The writer DuBose Heyward, best known for the 1925 novel “Porgy” that was later adapted into the opera “Porgy and Bess,” lived in the home from 1919 to 1924, historical documents show, and the home is on the National Register of Historic Places.

Spanning 5,336 square feet with five bedrooms, the house has a private courtyard and garden in the rear, said Charles Sullivan of Carriage Properties, who brokered a sale of the property in 2022 for $5.95 million. “It’s a little oasis back there.”

Windrush | Bedford Hills, N.Y.

Bought: $11.3 million in 2007

Sold: $7.1 million in 2012

Bessent bought this Westchester County estate in 2007, the year he joined Protégé Partners. The roughly 24-acre estate is located in Bedford Hills, a bucolic New York City suburb popular with celebrities. Built in the 1920s, the estate was modeled after Cassiobury, a 16th-century English country house. The estate was built by Harriet Hooper, whose husband Horace Hooper was the publisher of the Encyclopaedia Britannica, historical documents show. When Cassiobury was demolished in the 1920s, Harriet salvaged 10,000 Tudor bricks and used them to build her New York estate.

Spanning 6,700 square feet, the seven-bedroom residence has a grand curved staircase, oak floors and antique hardware and millwork, according to a prior listing description. The property also has two gatehouses, a barn, a pool and a goldfish pond.

La Gorce Estate | Miami Beach, Fla.

Bought: $9.5 million in 2010

Sold: $14.5 million in 2014

In 2010, Bessent bought a circa-1939 home on La Gorce Island, an exclusive guard-gated community connected by bridge to Miami Beach. The roughly 9,700-square-foot, seven-bedroom house is cast concrete and stucco with copper gutters and a clay barrel tile roof.

Bessent spent about a year renovating the Mediterranean-style residence, which is set on a roughly 1-acre lot with about 200 feet of water frontage. “He was really sensitive to the historic nature of the building,” said Cole Haynes, who worked on the renovation. Bessent refurbished architecturally significant details, including woodwork in the entry loggia.

In 2014, Bessent sold the property for $14.5 million to film producer Larry Kuppin and his wife, Minoush Kuppin, records show. To meet new flood-level requirements, the Kuppins got approval in 2021 to demolish the existing home and build a modern mansion in its place; it hasn’t yet been demolished. “It’s a shame the existing home was considered unsalvageable,” said Daniel Ciraldo of the Miami Design Preservation League. “We’ve had many spec builders come and tear down our historic gems.” The Kuppins didn’t respond to a request for comment.

Wyndecote | Southampton, N.Y.

Bought: $9.95 million in 2012

Sold: $19 million in 2019

After selling his Bedford Hills home, Bessent spent several years restoring a Southampton estate built in the late 19th century, an era when wealthy New Yorkers flocked to the area and built summer retreats near the beach.

The house is about 10,665 square feet with 10 bedrooms, a porte-cochere and a series of covered porches and verandas.

Working with local architect John David Rose, Bessent spent millions restoring the property. The entire house was lifted to replace the foundation, and the wood was removed to be restored.

Georgian Mansion | Greenwich, Conn.

Bought: $12.875 million in 2014

Sold: $13.065 million in 2017

Bessent and Freeman moved to Greenwich, Conn., in the mid-2010s, around the time Bessent launched Key Square, which is now based in nearby Stamford as well as London and Charleston. In Greenwich, an affluent town about 35 miles north of Manhattan, they bought a roughly 8-acre estate with a circa-1928, six-bedroom Georgian-style home spanning roughly 10,500 square feet, records show. The couple spearheaded a complete renovation and restoration of the property, according to a 2017 listing description. The property also has a pool, tennis court and carriagehouse with two apartments and additional staff rooms.

John Ravenel House | Charleston, S.C.

Bought: $6.5 million in 2016

Asking price: $22.25 million

The iconic pink house was originally built in the 1840s by the prominent Ravenel family, and it was restored after an 1886 earthquake, historical documents show. The property was being used as a bed-and-breakfast when Bessent and Freeman purchased it for $6.5 million in 2016, said Allen, who is marketing the home with colleague Scotty Brisson.

Bessent and Freeman spent three years taking the house down to the studs and rebuilding it with historically accurate details, including moldings and pine floors, Allen said. “They had to undo all of the rooms that were carved up into a mini hotel,” he said.

Measuring about 9,400 square feet with eight bedrooms, the house sits on a rare 0.41-acre double lot, Allen said. Wide piazzas on the second and third floors have views of Charleston Harbor and beyond, and the property has a separate three-bedroom carriagehouse, a poolhouse and a two-car garage.

Bessent and Freeman filled the home with antique furniture from around the world. The dining room has custom wallpaper that depicts their family (and dog) as well as historical scenes from around Charleston, Allen said.

Well known to locals, the property has received strong interest since hitting the market in October, Allen said. The couple “saw themselves staying in the home for a longer period of time, but as we all know—things change,” he said.

720 Park Avenue | New York, N.Y.

Bought: $19.25 million in 2017

Sold: $14.999 million in 2021

In 2017, Bessent traded the Greenwich estate for an apartment spanning two floors at Manhattan’s 720 Park Avenue, an exclusive brick-and-limestone cooperative building designed in the 1920s by noted architect Rosario Candela. The 17-story building is one of the most exclusive addresses in New York, requiring approval from the co-op board to buy into the building.

Bessent purchased the six-bedroom, roughly 7,000-square-foot residence from art-book publisher Mark Magowan and his wife, Nina Magowan, property records show. The Magowans had spent years renovating the apartment, which had four working fireplaces and a formal dining room with a walk-in silver closet paneled in tiger maple, said Kirk Henckels of Sotheby’s International Realty, who had the listing at the time.

Bessent took a steep loss when he sold the unit in 2021 after moving to Charleston. New York’s co-op market has been on a steady decline, losing about 30% of its value since 2007, Henckels said. But he said the unit wasn’t heavily marketed, which suggests Bessent was eager to move on. “The only way to read it is, he wanted to get it done,” Henckels said. “He didn’t even seem to try to get the higher figure.”

Bank Building | Charleston, S.C.

Bought: $2.6 million in 2020

Spanning roughly 4,700 square feet, the 3-story building has a courtyard in the rear, said Donna Webb of the Boulevard Company, whose clients sold the 18th-century building to Bessent and Freeman. At the time, she said, there was a bridal shop on the ground floor; the store now leases space upstairs. Bessent did a historic renovation of the property, which has offices and a guest suite, said Sullivan. “He’s protected the historic fabric of the property,” he said.

Chattooga Club | Cashiers, N.C.

Bought: $4.6 million in 2022