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Singer-songwriter Paul Simon, along with longtime collaborator Art Garfunkel, helped define the late-’60s music scene. With a legendary career spanning six decades, Simon is still going strong at the age of 80. Over the years, the musician has amassed a considerable fortune thanks to his many successful songs and high-profile projects. Still, when it came to selling his property in Connecticut, it wasn’t smooth sailing. And when Simon finally sold his house this summer, he accepted an offer well below his asking price.

Paul Simon is one of the most acclaimed songwriters of all time

Paul Simon home, Paul Simon house
Paul Simon in 2021 | Angela Weiss/AFP via Getty Images

Born in New Jersey on Oct. 13, 1941, Paul Simon developed an early affinity for music — a connection his parents nurtured, Biography reports. When he was just 11 years old, Simon met Art Garfunkel. The two became friends and eventually began performing together. As Simon & Garfunkel, the duo made waves, releasing songs such as “Mrs. Robinson” and “Bridge Over Troubled Water.”

Simon & Garfunkel parted ways in 1970, and although the songwriting team reunited several times over the ensuing decades, Simon embarked on a wildly successful solo career. His biggest hits include “You Can Call Me Al” and “The Boy in the Bubble.” Praised for his brilliant way with turns of phrase, Simon has earned 16 Grammy Awards.

Often cited as one of the greatest songwriters of all time, Paul Simon is a cultural icon and beloved elder statesman in the entertainment community.

Paul Simon lost millions on the sale of his Connecticut house

Over the decades, Paul Simon has owned several stately properties, but his Connecticut home is something special. He and his wife Edie Brickell bought the house in 2002 for around $16.5 million. They listed it on the market in 2019, but despite the home’s obvious charm and appeal, it didn’t sell until July 2022. According to The Real Deal, the home was initially listed for $13.9 million. Simon reduced the asking price to $11.9 million after failing to find a buyer, but it still took several years before the 32-acre estate sold.

The Real Deal notes that the property ultimately sold for $10.8 million, meaning Simon took a loss to the tune of several million dollars. The beautiful home, built in 1938, has six bedrooms, eight bathrooms, and a wealth of unique features, including an antique stone fireplace. According to Town and Country, the property also boasts has a pool, terraced pond, and detached cottage with a garage. For music fans, the estate is a paradise — Simon worked on several albums while living there.

The music legend’s other properties

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Although Paul Simon is probably thrilled to sell his Connecticut property finally, the music legend probably won’t be resting on his laurels. After all, he still owns several other residences around the United States where he can spend time relaxing and recording. As reported by The Real Deal, Simon still owns a duplex on Manhattan’s Upper East Side, a gorgeous oceanfront estate in Montauk, and a 10-acre spread in Allen, Texas.

It’s certainly good to be Paul Simon. And even though he took a loss on his Connecticut home, the musician likely isn’t sweating it much. Simon is worth an estimated $200 million, according to Wealthy Gorilla.