Paul Simon, Edie Brickell Lose Millions on Sale of New Canaan Estate

It took more than three years, but married musicians Paul Simon and Edie Brickell have at long last unloaded their sprawling estate just 45 minutes outside of Manhattan, in Connecticut’s ritzy and bucolic New Canaan, at $10.8 million.

The sale price is girthy by just about any standard but unfortunately for the May-December pair — married 30 years, 80-year-old Simon is 25 years Brickell’s senior – it’s a staggering $5.7 million below the $16.5 million records show the innovative singer-songwriters as paid for the nearly 32-acre spread about 20 years ago. According to reports from when the property first popped up for sale in 2019 with a too-optimistic price of $13.9 million, Simon recorded “many of his hit albums here.”

While a pocketbook-draining loss like this certainly chaps the hides of even those with coffers overflowing with cash, it would nonetheless seem comfortably weathered by the 12-time Grammy-winning “Bridge Over Troubled Waters” singer, who sold his entire catalog to Sony Music Publishing last year for an undisclosed amount that by some reports was around a quarter billion bucks.

A whitewashed brick Georgian mansion designed by architect Harold Reeve Sleeper, completed in 1938, the estate’s main residence is an elegant yet relaxed complement to the acres of rolling lawns, perennial gardens and surrounding woodlands. There are half a dozen bedrooms and 8 bathrooms, plus a trio of powder rooms, throughout the three-story home that lends itself to both gracious entertaining and relaxed family living.

The 31-foot-long foyer leads to a 750-square-foot living room with an antique stone fireplace and French doors to a spacious, tile-floored sunroom. Elsewhere there’s a paneled library with a curved corner fireplace, a up-to-date eat-in kitchen that flows easily into the dining room and, between the kitchen and the three-car garage, a gigantic mudroom.

Each of the main house’s five guest bedrooms boasts a private bath. One of them also offers a private sitting room with fireplace, while the primary suite has two bathrooms along with a closet-lined dressing gallery, a fireplace and a large terrace from which to survey the land.

The park-like grounds provide a secluded idyll with sweeping meadows, walled gardens and a swimming pool sited on a grassy plateau with meditative views over a tranquil private pond. Just inside the main gates and a good distance from the main house, a 2,400-square-foot, three-bedroom cottage, which the couple used as a recording studio, makes a perfect caretaker’s home or guesthouse.

The property was listed with Taylor Tait and Libby Mattson of Houlihan Lawrence, while the buyer was represented in the deal by Bruce Baker of William Pitt Sotheby’s International Realty.

Quietly home (or once home) to scads of business tycoons, sports stars, journalists and entertainment industry types, David Letterman, Glenn Beck and Chris Meloni among them, tiny and affluent New Canaan is perhaps best known as home to Philip Johnson’s Glass House.

While they’re no doubt relieved to have finally shed their New Canaan estate, Simon and Brickell still preside over at least three other residences: a duplex apartment in the same building on Manhattan’s Upper West Side where some of the other units are owned by Annie Leibovitz, Lorne Michaels and Robert De Niro; a 30-acre oceanfront compound in the Hamptons, in the far reaches of Montauk; a ten-acre estate in Allen, Texas, on the semi-rural outskirts of Dallas.