88 Cedar Cliff Road in Riverside, CT: Dan Gressel’s Waterside Tudor Mansion

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.