108 Cedar Cliff Road

Riverside, CT 06878

$100,000,000 PRICE
8 Beds
9/5 Baths
13,163 Sqft
2.91 Acres
1930 Built

Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside's prestigious Indian Head Association, this storied property occupies the historic grounds of railroad magnate Henry Francis Shoemaker's former compound--a Gilded Age legacy that later served as the backdrop for the iconic Cedar Cliff Beach Club of the 1920s. The estate bears the name Shoemaker originally gave his villa, 'Cedar Cliff'--a designation that eventually defined the very road on which it stands. Elevated high above the flood zone and offering 1,250+ feet of direct water frontag the property unfolds with extraordinary scale and privacy. A sweeping, manicured lawn rolls gracefully toward the shoreline, creating a striking foreground to the panoramic coastal vistas and an exceptional setting for grand-scale entertaining. Each of the eight oversized bedrooms is oriented to capture breathtaking water views, while interiors blend the romance of pre-war craftsmanship with modern refinement--soaring ceilings, intricate millwork, antique wood floors, a three-level elevator and a professional recording studio. The East Wing, constructed in the early 2000s, introduces a new dimension of contemporary luxury, anchored by a sophisticated primary suite and complemented by a custom office, wine cellar, and private theater capable of accommodating up to twenty guests. The grounds rival those of a world-class private resort. A substantial stone pier and deep-water dock provide immediate access to open water, while a seaside tennis court with pergola and lighting offers championship-level play. At the water's edge, a pool and spa are paired with a fully realized cabana featuring a fitness center, kitchenette, and changing rooms. Sculpted into the eastern landscape, a series of stone terraces with a bluestone bar directly overlook Greenwich Cove and the vast protected expanse of Greenwich Point Park. Meticulously maintained and thoughtfully enhanced, the estate includes a newly installed Ludowici terra cotta roof, rebuilt sun decks, custom East Wing windows, and a full-property generator--ensuring seamless comfort and continuity. With access to a private beach and watercraft facilities, and located less than an hour from Manhattan and minutes from Westchester County Airport, the property offers a rare convergence of seclusion, scale, and global accessibility. Cedar Cliff is a singular offering for the most discerning buyer--an incomparable experience of refined luxury, inviting residents and their guests to revel in the natural beauty of one of the finest estates on the East Coast of the United States.

Additional Information

ADDITIONAL INFORMATION

BASEMENT DESCRIPTION: Finished
ELEMENTARY SCHOOL: Riverside
MIDDLE SCHOOL: Eastern
ON MARKET DATE: 2026-05-18
SEWER: Septic Tank
STYLE: Mediterranean
TAX AMOUNT: $206,971
TYPE: Residential
YEAR BUILT: 1930

INTERIOR/EXTERIOR FEATURES

BEDS: 8
CONSTRUCTION MATERIALS: Stucco
COOLING: Central Air
EXTERIOR FEATURES: Dock, Terrace, Deck, Pool (Private)
FULL BATHS: 9
HEAT: Natural Gas, Forced Air
INTERIOR FEATURES: Kitchen Island
ROOF: Other, Tile

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Location for 108 Cedar Cliff Road, Riverside, CT

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Community

Riverside

Fairfield County, Connecticut

Riverside, one of Greenwich’s popular upscale, suburban neighborhoods, is situated between the town’s Cos Cob and Old Greenwich neighborhoods in lower Fairfield County. The vibrant, picturesque area...

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New Canaan Brokerage
26 Cherry Street
New Canaan, CT 06840
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Information provided by the Greenwich Multiple Listing Service, Inc. © 2026. Listing Courtesy of Leslie McElwreath of Sotheby's International Realty (203.869.4343). Data is updated as of 16:54 PM on 05/19/2026