108 Cedar Cliff RD, Riverside, CT 06878
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108 Cedar Cliff RD, Riverside, CT 06878
108 Cedar Cliff RD, Riverside, CT 06878
108 Cedar Cliff RD, Riverside, CT 06878
108 Cedar Cliff RD, Riverside, CT 06878
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$ 100,000,000
Est. payment /mo
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108 Cedar Cliff RD Riverside, CT 06878

8 Beds

11.5 Baths

13,163 SqFt


UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 13,163 sqft

Price per Sqft $7,597

MLS Listing ID 125034

Style Mediterranean

Bedrooms 8

Full Baths 9

Half Baths 5

HOA Y/N No

Year Built 1930

Annual Tax Amount $206,971

Lot Size 2.910 Acres

Acres 2.91

Property Sub-Type Single Family Residence

Source Greenwich Association of REALTORS®

Property Description

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.

Location

State CT

County Fairfield

Zoning RA-1

Rooms

Other Rooms Greenhouse, Pool House

Basement Finished

Interior

Interior Features Kitchen Island, Sep Shower

Heating Natural Gas, Forced Air

Cooling Central Air

Fireplaces Number 10

Inclusions Washer/Dryer, Call LB, All Kitchen Applncs

Equipment Generator

Fireplace Yes

Window Features Bay Window(s),Double Pane Windows

Laundry Laundry Room

Exterior

Exterior Feature Dock, Fountain

Parking Features Attached Garage

Waterfront Description Deep Water,LI Sound,Waterfront

Roof Type Other,Tile

Porch Terrace, Deck

Building

Lot Description Cul-De-Sac, Parklike

Sewer Septic Tank

Water Public

Architectural Style Mediterranean

Structure Type Stucco

New Construction No

Schools

Elementary Schools Riverside

Others

Senior Community No

Tax ID 05-1377

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108 Cedar Cliff RD