Real Estate

Paul Simon sells Connecticut estate at multi-million dollar loss

There’s no diamonds on the soles of this sale. 

Singer/songwriter Paul Simon, 80 and his wife, 56-year-old singer Edie Brickell, have finally sold their 8,800-square-foot New Canaan, Conn. mansion — albeit at a huge loss. 

The musical duo purchased the almost 32-acre, 84-year-old property about 20 years ago for $16.5 million — but after more than three years of trying to resell it, only managed to make $10.8 million, Dirt reported

The musicians first put the Georgian-style estate on the market in 2019 with a price tag of $13.9 million. Not only does the sprawling main house boast six bedrooms, three powder rooms and seven full bathrooms — but the Grammy Award-winning Simon “recorded many of his hit albums here,” Town & Country reported at the time. 

Neither Simon’s legacy in the space nor its pond, terraced pool, walled gardens, courtyard or 2,400-square-foot guest cottage with a garage could sell the pad. It only managed to sell three years later and at a $3.1 million discount off the original ask.

paul simon new canaan sale
An aerial shot of Paul Simon and Edie Brickell’s former home.
EagleView
The celebrity couple finally sold the property this year, albeit at a hefty loss.
EagleView
paul simon new canaan sale
The singers have been trying to offload the property since 2019.
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paul simon new canaan sale
They bought the estate about 20 years ago.
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paul simon new canaan sale
Paul Simon and wife Edie Brickell pose at the Opening Night After Party for the new musical “Bright Star” on Broadway at Gotham Hall on March 24, 2016 in New York City.
Bruce Glikas/FilmMagic

In addition to bragging rights regarding its celebrity former owners, the three-story home also comes with a 31-foot-long foyer, a 750-square foot living room and a tile-floored sunroom, according to Dirt. There’s a paneled library, a very large mudroom and an ensuite bath in every bedroom. It was built in 1938 by architect Harold R. Sleeper.

“A separate 3-bedroom cottage offers a quintessential escape to be as creative and self-indulgent or as engaging and social as you wish,” notes an old listing site, which still lists its sale price at $12 million. “This uniquely serene estate has been sensitively maintained to provide the ultimate in peace, privacy, luxury and tranquility and is just 45 miles from NYC.”

Even without their New Canaan house, Simon and Brickell still have three residences between them: An Upper West Side duplex, a Montauk property and a compound just outside Dallas, Dirt reported.

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