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108 Cedar Cliff Rd, River...

house view

porch

Est $ 561,220/mo

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108 Cedar Cliff Rd, Riverside, Connecticut, 06878

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8

Bed

14

Bath

13163

Sqft

Overview

Property Type

Home

Property Status

Sale

Year Built

1930

Days on RealtySearch

-

Active Status

Active

Last Sold

$7,800,000 in 1994

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 In...

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Neighborhood

108 Cedar Cliff Rd is located in neighborhood in the city of Riverside,CT

Property History

Date

2026-05-18

Event

Listed

Price

$100000000

Price/Sq Ft

13163

Source

Greenwich

Date

1994-07-27

Event

Sold

Price

$7800000

Price/Sq Ft

Source

Public Record

Date

1988-04-21

Event

Sold

Price

$4650000

Price/Sq Ft

Source

Public Record

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Name

Email

Phone

Comments

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Est

get pre-qualify

108 Cedar Cliff Rd, Riverside, Connecticut, 06878

Get Free FICO® Credit Score

8

Bed

14

Bath

13163

Sqft

Overview

Property Type

Home

Property Status

Sale

Year Built

1930

Days on RealtySearch

-

Active Status

Active

Last Sold

$7,800,000 in 1994

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 In...

More Details

Neighborhood

is located in neighborhood in the city of ,

Property History

Date

2026-05-18

Event

Listed

Price

$100000000

Price/Sq Ft

Source

View More Details

Request Info

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.

Presented by:

Leslie McElwreath

Brokered by:

Sotheby's International Realty - Greenwich Brokerage

Broker Location

,