Address
108 Cedar Cliff Road, Riverside, CT
Price
$ 100,000,000
Property Attributes
- MLS#125034
- TypeSingle Family
- Listing Status Active
- CountyFairfield
- CityRiverside
- AreaRiverside
- NeighborhoodRiverside
- Zip06878
- Style
- Year Built1930
- Taxes$ 174051
- Price$ 100,000,000
- Bedrooms8
- Full Bathrooms9
- Half Bathrooms5
- Sqr Footage13163
- Lot Size2.91 Acres
Data Source:
Greenwich MLS (GRWMLS)
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.
| Elementary School | Middle School |
|---|---|
| Riverside Elementary School | Eastern Middle School |
| Price History | |
|---|---|
| 5/18/2026 | Listed $100,000,000 |
General Features
| Sewer | Septic Tank |
|---|---|
| Heating | Natural Gas,Forced Air |
| Cooling | Central Air |
| Roof | Other,Tile |
| Zoning | RA-1 |
| Patio/Porch Features | Terrace,Deck |
| Architectural Style | Mediterranean |
| Construction Materials | Stucco |
| Exclusions | Call LB |
| Year Built | 1930 |
| Property Subtype | Single Family Residence |
| Waterfront Features | Deep Water,LI Sound,Waterfront |
| County | Fairfield |
| Property Type | Residential |
| Attached Garage | false |
| Other Structures | Greenhouse,Pool House |
| Full Baths | 9 |
| Status | Active |
| City | Riverside |
| MLS Area | 1 - Riverside |
| Lot Size Units | Acres |
| Lot Size Square Feet | 126759.6 |
| Elementary School | Riverside |
| Tax Annual Amount | 174051.99 |
| Middle/Junior High School | Eastern |
| Property Condition | Antique |
| MLS Area Minor | 1 - Riverside |
| Virtual Tour | https://players.brightcove.net/5782886755001/rJlOfaQNgQ_default/index.html?videoId=ref:sir_listings_00613355 |
| Standard Status | Active |
| Tax Assessed Value | 17190320 |
Interior Features
| Interior Amenities | Kitchen Island,Sep Shower |
|---|---|
| Basement | Finished |
| Total Fireplaces | 10 |
| Air Conditioning Y/N | true |
| Heating Y/N | true |
| Window Features | Bay Window(s),Double Pane Windows |
| Fireplace Y/N | true |
| Half Baths | 5 |
| Laundry Features | Laundry Room |
| Total Bedrooms | 8 |
| Total Baths | 14 |
Exterior Features
| Exterior Amenities | Dock,Fountain |
|---|---|
| Parking Features | Attached Garage |
| Lot Features | Cul-De-Sac,Parklike |
| Water Source | Public |
| Inclusions | Washer/Dryer, Call LB, All Kitchen Applncs |
| Lot Size Area | 2.91 |
| Building Area Total | 13163 |
| Lot Size Acres | 2.91 |
| Waterfront Y/N | true |
| Other Equipment | Generator |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 06878
Price
Taxes
Year Built
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