Perched in timeless elegance atop a spectacular 2.91-acre gated peninsula, Cedar Cliff commands best-in-class views of the Manhattan skyline and the shimmering waters of Long Island Sound. Privately situated along a secluded road within Riverside’s prestigious Indian Head Association, this extraordinary Mediterranean villa occupies the historic grounds of railroad magnate Henry Francis Shoemaker’s former compound—a Gilded Age legacy that later became home to the celebrated Cedar Cliff Beach Club of the 1920s.
Elevated well above the flood zone and boasting more than 1,250 feet of direct waterfront frontage, the property unfolds with remarkable scale, privacy, and presence. A sweeping expanse of manicured lawn cascades gracefully toward the shoreline, creating a dramatic foreground to panoramic coastal vistas and an unrivaled setting for grand-scale entertaining.
Each of the estate’s eight generously proportioned bedrooms is oriented to capture breathtaking water views. Throughout the residence, soaring ceilings, intricate millwork, antique hardwood floors, a three-level elevator, and a professional recording studio blend the romance of prewar craftsmanship with modern sophistication.
The East Wing, completed in the early 2000s, introduces an additional layer of contemporary luxury. Anchored by an elegant primary suite, it also features a bespoke executive office, climate-controlled wine cellar, and a private theater accommodating up to twenty guests.
The grounds rival those of a world-class resort. A substantial stone pier and deep-water dock provide immediate access to open water, while a waterfront tennis court—complete with pergola and professional lighting—offers championship-caliber play. At the shoreline, a pool and spa are complemented by a fully appointed cabana featuring a fitness center, kitchenette, and changing facilities.
Address: 108 Cedar Cliff Rd, Riverside, CT 06878
Listing Price: $100,000,000 million
Square feet: 13,163
Bedrooms and Bathrooms: 8 bedrooms and 14 bathrooms
Zillow listing for 108 Cedar Cliff Rd, Riverside, CT
