A Riverside estate in Greenwich, CT, has come to market with a new offering price of $14.75 million—$10 million less than its initial asking price of $25.5 million. Designed by architect Douglas VanderHorn, the 2008 custom-built home honors early 20th-century architecture while offering breathtaking views of the Long Island Sound.
The property sits on 1.77 acres in the Indian Head Association, a prestigious gated community with private beach access. The estate takes inspiration from a 1920s Tudor-style cottage originally located on the site. The original structure, now transformed into a two-bedroom, two-bathroom guest wing, connects to the main house through a stone breezeway.
The main home, measuring over 9,000 square feet, features five bedrooms and six bathrooms. Its design highlights include custom millwork, a grand entryway with black-and-white marble flooring, an oak-paneled living room, and seven fireplaces.
Modern amenities include a state-of-the-art home theater, a gym, and a spacious lower-level family room. Outside, the property includes landscaped gardens, a pool and spa, a pool house, and multiple stone terraces for outdoor relaxation and entertainment.
Riverside: A Picturesque Neighborhood in Greenwich
Riverside, a charming neighborhood in Greenwich, is renowned for its historic appeal and scenic beauty. Located along the Long Island Sound, the area provides stunning waterfront views, convenient access to parks, and a strong sense of community. The Indian Head Association further enhances its appeal with exclusive amenities like a private beach.
Investor Dan Gressel’s 2008 Purchase
Investor and economist Dan Gressel acquired the property in 2008 for $11.75 million. Gressel, a proponent of free-market principles, grew up in Ohio and was inspired by statistician Milton Friedman’s columns in Newsweek. His interest in economics and politics deepened while studying as an undergraduate at Ohio State University. Gressel has been associated with Hedge Fund Teleos Management LLC, which at its peak managed over $750 million in assets.
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
