Paul Simon and Edie Brickell Sell Their Connecticut Estate at a Loss

Singer-songwriter power couple Paul Simon and Edie Brickell have finally sold their sprawling estate in New Canaan, Connecticut, though at a multi-million-dollar loss.

The pair bought the 31.8-acre property for $16.5 million in 2002 from the estate of investor and philanthropist Charles A. Dana Jr., who had owned the property for nearly five decades, property records show.

Mr. Simon, 80—whose music career has spanned six decades, starting with Simon and Garfunkel—and Ms. Brickell, 56, first listed the estate in April 2019 for $13.9 million and dropped the price to $11.9 million in November 2020.

After switching to a new brokerage, the property came back to the market for $12 million in March 2021. It sold for $10.8 million last Friday, listing records show.

The transaction has yet to appear on property records. Mansion Global could not determine the buyer’s identity.

Despite being massive in size, the English country-style estate is completely enclosed to create a private sanctuary complete with open rolling landscape, woodland trails, brooks, natural ponds and waterfalls, according to the most recent listing with Taylor Tait and Libby Mattson of Houlihan Lawrence.

They declined to comment on the sale.

There are two homes on the property offering a total of 8,811 square feet of living space with six bedrooms and 11 bathrooms, according to the listing.

The main residence, designed in 1938 by architect Harold R. Sleeper, features soaring ceilings, fireplaces, oversized windows and hand-crafted millwork. Formal living and dining rooms open to terraced patios, gardens and the pool.

A separate cottage offers an additional 1,483 square feet of living space with its own private driveway, parking and garage, the listing said.

Mr. Simon, who has won 16 Grammys and penned iconic songs including “The Sound of Silence,” “Bridge Over Troubled Water” and many more, could not be immediately reached for comment. Ms. Brickell, an alternative rock singer known for 1988’s debut album “Shooting Rubberbands at the Stars,” did not respond to a request for comment sent to her agency in time for publication. They have been married since 1992 and have three children together.

New Canaan is about 45 miles north of Manhattan. The median sales price of single-family homes there was $1.7 million in the second quarter, according to data from Douglas Elliman.