640 Sasco Hill Road in Fairfield, CT: Howard Sosin’s Mansion

640 Sasco Hill Road in Fairfield, CT is a Roger Ferris-designed, six-level mansion with 13,000 square feet of living space. It features 10 bedrooms, 18 bathrooms, and two pools—an outdoor oval pool and a 25-yard indoor marble pool beneath a skylight ceiling.

The top floor is dedicated to the private primary suite with a spacious terrace offering views of New York City. The second floor includes six en-suite bedrooms and a media room. Additional features include a squash court, gym, and landscaped gardens.

Floor-to-ceiling windows and French doors provide stunning views of Southport Harbor, while multiple granite patios create an ideal flow between indoor and outdoor spaces. The property is currently on the market and offered fully furnished for $11,989,000 (as of 1/10/2025).

Howard Sosin: The Man Behind the Mansion

Howard Sosin, the current owner, is a former Columbia University professor who founded the financial powerhouse AIG. He made headlines in 1993 when he exited the company with a staggering $182 million payout. He later launched ventures in the pharmaceutical and golf equipment industries.

In 2005 his divorce from Susan Sosin resulted in a $45 million settlement, one of the largest of its kind at the time. While Sosin retained $89 million in bank accounts, 10 luxury cars, $960,000 in private club memberships, and $22 million in fine art, the trial testimony revealed a marriage rocked by infidelity.

While Howard focused on growing his business empire, Susan pursued adventurous hobbies like heli-skiing and rock climbing. Her 1996 affair with a climbing guide and a later relationship with a man she met on a flight to China ultimately contributed to the couple’s split.

The Bradley Cooper Rumors

Adding a dose of Hollywood drama to the property’s lore, rumors recently circulated that actor Bradley Cooper was renting the estate. The buzz grew so intense that locals began leaving baked goods and dinner invitations at the gate, hoping for a glimpse of the actor. Rick Higgins, a local broker, had to publicly clarify: “Bradley Cooper…has NOT purchased 640 Sasco Hill Road.”