36-38 Game Cock Road in Greenwich, CT, offers a rare opportunity to own a private island with practical waterfront features and the convenience of a private bridge. Spanning 1.15 acres, this property has served as a multi-generational family retreat for more than four decades. It is currently listed for sale at $22,000,000 (as of 1/27/2025).
Built in 1936, the main house is a ~6,000-square-foot residence with seven bedrooms and five-and-a-half baths. Two wood-burning fireplaces, a basement, and a garage are among its features. Large windows throughout provide expansive views of the Long Island Sound. A guest house, spanning ~3,000 square feet, includes three en-suite bedrooms, making it an ideal space for hosting visitors or extended family.
The property offers extensive waterfront amenities, including a deep-water dock that can accommodate multiple boats and a boathouse for storage and entertaining. A private beach and a dedicated outdoor clam bake area provide additional spaces for gatherings. Formal gardens, outdoor decks, and landscaped grounds complete the outdoor experience. A unique feature is the property’s private bridge, offering convenient access to the island while ensuring privacy.
Ownership Through the Decades
Gary Lee Swenson, an investment banker and Greenwich Academy trustee, purchased the property in the 1980s. Known for his community involvement and leadership, Swenson oversaw the property’s maintenance and ongoing renovations, adding a variety of modern updates.
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
