$100,000,000
8 Beds
11.5 Baths
13,163 sqft (on 2.91 acres)
108 Cedar Cliff Rd, Riverside, CT 06878
Est. Mortgage $675,839/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 1930
2.91 acre lot
$7,597/sqft
Local Information
- Map ViewExplore the area around 108 Cedar Cliff Rd.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
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.
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.
Last check for updates: about 5 hours ago
Listing courtesy of Leslie McElwreath, (917) 539-3654
Sotheby's International Realty
Source: Greenwich MLS, Inc., MLS#125034
Also Listed on Greenwich MLS, Inc..
Home Details for 108 Cedar Cliff Rd
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Interior Details Basement: Finished |
Beds & Baths Number of Bedrooms: 8Number of Bathrooms: 14Number of Bathrooms (full): 9Number of Bathrooms (half): 5 |
Dimensions and Layout Living Area: 13163 Square Feet |
Appliances & Utilities Laundry: Laundry Room |
Heating & Cooling Heating: Natural Gas,Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas |
Fireplace & Spa Number of Fireplaces: 10Has a Fireplace |
Windows, Doors, Floors & Walls Window: Bay Window(s), Double Pane Windows |
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Exterior Home Features Roof: Other TilePatio / Porch: Terrace, DeckOther Structures: Greenhouse, Pool HouseExterior: Dock, FountainHas a Private Pool |
Pool Pool |
Frontage WaterfrontWaterfront: Deep Water, LI Sound, WaterfrontOn Waterfront |
Water & Sewer Sewer: Septic Tank |
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Days on Market: 125 |
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Year Built Year Built: 1930Year Renovated: 2025 |
Property Type / Style Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceArchitecture: Mediterranean |
Building Construction Materials: StuccoNot a New Construction |
Property Information Condition: AntiqueIncluded in Sale: Washer/Dryer, Call LB, All Kitchen ApplncsParcel Number: 051377 |
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Price List Price: $100,000,000Price Per Sqft: $7,597 |
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MLS Status: Active |
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Direction & Address City: Riverside |
School Information Elementary School: RiversideJr High / Middle School: Eastern |
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Listing Agent Listing ID: 125034 |
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Building Area Building Area: 13163 Square Feet |
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Lot Area: 2.91 Acres |
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Mobile Home Park Mobile Home Units: Feet |
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BasementMls Number: 125034 |
Around this home
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Riverside
At least 48 Trulia users voted on each feature.
92 % Say parking is easy
91 % Say it's dog friendly
90 % Say yards are well-kept
90 % Say people would walk alone at night
89 % Say kids play outside
87 % Say car is needed
87 % Say there's holiday spirit
86 % Say they plan to stay for at least 5 years
82 % Say it's quiet
75 % Say neighbors are friendly
74 % Say there's wildlife
71 % Say there are sidewalks
58 % Say it's walkable to restaurants
55 % Say it's walkable to grocery stores
53 % Say there are community events
52 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
Market trends in Greenwich
Last updated August 2026
Avg. sale price
$2.58M
$150KMoM
Sale-to-List Price
104.8%
1.0%MoM
Price per sq ft
$825
$1MoM
Available listings
152
30MoM
Home Value
Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.60 | Single-Family Home | $12,900,000 | 12/29/25 | 6 | 7 | 9,418 | |
0.33 | Single-Family Home | $4,475,000 | 08/17/26 | 4 | 3.5 | 6,915 | |
0.70 | Single-Family Home | $10,750,000 | 11/14/25 | 5 | 5 | 6,577 | |
0.88 | Single-Family Home | $7,750,000 | 07/15/26 | 6 | 6 | 8,364 | |
0.71 | Single-Family Home | $4,650,000 | 11/05/25 | 4 | 5 | 4,097 | |
1.04 | Single-Family Home | $8,300,000 | 04/06/26 | 6 | 8.5 | 9,485 | |
1.20 | Single-Family Home | $40,000,000 | 11/19/25 | 6 | 9.5 | 11,500 | |
1.05 | Single-Family Home | $9,750,000 | 10/17/25 | 6 | 7 | 8,896 | |
0.89 | Single-Family Home | $5,700,000 | 11/18/25 | 6 | 6 | 6,673 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.13 | $11,028,000 | 6 | 7.5 | 9,258 | Off Market | |
0.13 | $14,271,400 | 7 | 9.5 | 9,416 | Off Market | |
0.18 | $12,128,200 | 7 | 8 | 8,903 | Off Market | |
0.18 | $6,865,100 | 5 | 4 | 4,705 | Off Market | |
0.30 | $3,528,900 | 4 | 2.5 | 3,138 | Off Market | |
0.28 | $11,586,400 | 6 | 7.5 | 9,995 | Off Market | |
0.32 | $3,976,100 | 5 | 4 | 3,764 | Off Market | |
0.34 | $5,848,800 | 4 | 5.5 | 4,159 | Off Market | |
0.33 | $4,475,000 | 4 | 3.5 | 6,915 | Recently Sold | |
0.36 | $6,048,000 | 5 | 5.5 | 7,142 | Off Market | |
0.41 | $5,600,000 | 5 | 3.5 | 4,324 | For Sale |
Price and Tax history
| Date | Event | Price |
|---|---|---|
May 18, 2026 Source: Greenwich MLS, Inc. #125034 | Listed For Sale | $100,000,000 |
Jul 27, 1994 Source: N/A | Sold | $7,800,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $206,971 | $17,190,320 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Leslie McElwreath, Sotheby's International Realty
Agent Phone: (917) 539-3654
Listing data courtesy of Greenwich MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to
identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.
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Frequently asked questions about 108 Cedar Cliff Rd
- What is the estimated monthly payment for 108 Cedar Cliff Rd?Based on a $100,000,000 list price with 20% down at today's rates, the estimated monthly payment for 108 Cedar Cliff Rd in Riverside, CT is approximately $686,107 (about $545,199 principal & interest, $140,833 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- How does the list price for 108 Cedar Cliff Rd compare to homes in Riverside?108 Cedar Cliff Rd in Riverside, CT is listed at $100,000,000, about 3771% above the $2.58M median sale price in Riverside.
- What do residents say about Riverside?Residents describe Riverside, CT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See homes for sale in Riverside, CT.
- What are the closest schools to 108 Cedar Cliff Rd?The closest schools to 108 Cedar Cliff Rd in Riverside, CT are Eastern Middle School (rated 10/10), Greenwich High School (rated 10/10), Riverside School (Elementary, rated 10/10).
- Does 108 Cedar Cliff Rd have air conditioning?Yes, 108 Cedar Cliff Rd in Riverside, CT has air conditioning.
- Does 108 Cedar Cliff Rd have a pool?Yes, 108 Cedar Cliff Rd in Riverside, CT has a pool.
108 Cedar Cliff Rd, Riverside, CT 06878 is a 8 bedroom, 14 bathroom, 13,163 sqft single-family home built in 1930. 108 Cedar Cliff Rd is located in Riverside, Riverside. This property is currently available for sale and was listed by Greenwich MLS, Inc. on May 18, 2026. The MLS # for this home is MLS# 125034.