Located in the Field Point Circle Association in Greenwich, CT, the estate at 100 Field Point Circle offers 2.46 landscaped acres and 340 feet of private shoreline along Long Island Sound. The property was previously owned by Thomas Watson Jr., the legendary chairman of IBM who guided the company during a transformative era from 1956 to 1971.
In 2006, the Watson family sold the property to Brett Barakett, Chair of Tremblant Capital, who reimagined the site by replacing the original structure with a ~10,000-square-foot custom-built Georgian-style mansion. The property made headlines in late 2021 when it sold for $50 million, ranking as one of the region’s most significant real estate transactions.
Designed by the award-winning architecture firm Shope Reno Wharton Associates, the stone-clad home has eight spacious bedrooms and features expansive terraces, an indoor pool, and an outdoor pool, each positioned to maximize the panoramic views of the water. A private beach and a deep-water dock further enhance the coastal lifestyle.
Field Point Circle is regarded as one of Greenwich’s most exclusive neighborhoods, offering a gated and highly secure community. The property itself is elevated and protected from flooding. Its beautiful English gardens, sweeping lawns, and stone pathways create an atmosphere of timeless sophistication. Inside, the residence showcases interiors that blend traditional Georgian details with modern touches, from grand fireplaces to sun-drenched living spaces that seamlessly connect with the outdoors.
The most recent owner, whose identity is shielded behind a limited liability corporation, has already begun planning updates to the property, including the construction of a large gymnasium.
Cress is an innovative real estate advisory firm representing buyers and sellers of high-end properties throughout Fairfield County, CT and beyond. On the sell side, Cress delivers marketing-driven support designed to expand visibility and maximize outcomes. Through its co-listing model, Cress partners alongside listing agents to provide digital-first distribution, high-quality content creation, and proactive demand generation strategies that extend well beyond traditional MLS exposure.
On the buy side, Cress offers flat-fee representation and commission rebate programs that bring efficiency and transparency to luxury transactions while maintaining a high standard of service. Known for strategic insight, modern marketing execution, and deep local knowledge, Cress provides a smarter, more aligned approach to buying and selling real estate.
For more information, visit www.callcress.com.
Doug Cress
(212) 203-5251
doug@cress.co
License #RES.0832278
Fairfield County, CT
Enterprise Realty Inc.
License #REB.0751297
45 Huntington Plaza
Shelton, CT 06484
