Once Fairfield's Priciest Estate, 20-Acre Property To Become Subdivision

FAIRFIELD, CT — A 20-acre waterfront estate that was once the most expensive residential property in town has been sold to a developer, who plans to turn the site into a seven-home subdivision.

Known in Fairfield as the Jack property, for years the land at 1143 Sasco Hill Road was owned by former Lehman Brothers co-chief operating officer Bradley Jack. In 2011, the estate had a market value of nearly $35 million. However, the site became tax delinquent in 2013, and was recently purchased for only $17.5 million by 1143 Sasco Hill Road LLC, according to town officials.

“I think all sides are very happy,” First Selectwoman Brenda Kupchick said when she announced the sale at a Board of Selectmen meeting in August.

Fairfield has received all of the roughly $7 million in back-taxes owed on the property, town officials confirmed.

The subdivision and coastal site plan for the development that will replace the Jack estate was approved in July by the Town Plan & Zoning Commission.

When it was owned by Jack, the property on Long Island Sound included a nearly 14,000-square-foot home, three guest houses, a gatehouse and a boathouse, as well as a beach, pool, tennis court and barn.

The property became delinquent not long after Jack, who died in 2019 at age 60, was arrested and charged twice in connection with prescription forgery, first in Fairfield and later in Westport, where he was living at the time, according to multiple news reports.