The family built a 1,800-square-foot pool house in 1998, which has a living/dining room, two bedrooms, and two bathrooms; they built one barn to house farm equipment (“the flag barn”), and then another, 8,500-square-foot barn, house, and farm office. They also extensively renovated the four-bedroom, 2,000-square-foot estate manager’s residence in 2009.

Including the purchase of the land, Fitzgerald says he put in about $8 million into the property. (That doesn’t include maintenance or upkeep.)

Fitzgerald and his family started to raise Black Angus cattle. “We were making a good go of it,” he says. “We got a James Beard award for our beef, and [former Vanity Fair editor] Graydon Carter was serving our meat in his restaurants in New York.”

Fitzgerald maintained a full-time finance job, but would take his own beef to the farmer’s market in New Canaan. “It was fantastic,” he says. “You have to stay close to your customer. I was fully engaged in this operation; before I had a hedge fund I worked at Goldman, and these are both jealous positions, requiring time for your primary livelihood. But I put a lot of time in” at the farmer’s market, too.

In the meantime, his three sons, starting from the age of six, were charged with running a summer farm stand.

“It forced them to understand how to take responsibility for looking after their crops and to present their vegetables to the adults who’d come to purchase them,” Fitzgerald says. “It encouraged them to be comfortable engaging with both their peers and adults.”

“It was everything that we hoped it might be in terms of an experience for our children,” Fitzgerald explains of his decision to wind down about five years ago. “However, we learned that the concept of ‘sustainable agriculture,’ at least in terms of running an all-natural Black Angus cattle operation in Connecticut, appears to be an oxymoron. We learned that building a best-in-class sustainable beef business required a not insignificant second income to sustain the effort.”

Saying Goodbye
The family got a solid quarter-century out of the estate but even so, Fitzgerald is torn about the sale.

The land “is so unique,” he says. “I know many people say that about their property, and many of them are, not necessarily in a good way. But this offering is differentiated by every other property in Litchfield County by its scale, its scarcity, and its quality,” he continues. “The property offers a rare combination of near 360-degree views to the horizon, open fields, woods, and approximately 25,000 square feet of beautifully maintained homes and outbuildings.”

“The goal at this juncture,” he says, “is to find a family, or a couple, who will value the experience as much as we have.”