108 Cedar Cliff Rd, Riverside, CT 06878
Property image
Property image
FOR SALE
3D VIEW
2.91 ACRES

108 Cedar Cliff Rd
Riverside, CT 06878

Riverside
  • 8 Beds
  • 11.5 Baths
  • 13,163 sqft (on 2.91 acres)

$100,000,000

Est. Mortgage $653,421/mo*
Get Pre-Qualified

$100,000,000

Est. Mortgage $653,421/mo*
Get Pre-Qualified
8 Beds
11.5 Baths
13,163 sqft
(on 2.91 acres)

Home Highlights

Outdoor
Deck, Pool
Climate Control
Heating & Cooling
Price/Sqft
$7,597
Listed
76 days ago

Local Information

  • Map ViewExplore the area around 108 Cedar Cliff Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

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.

Home Details for 108 Cedar Cliff Rd

Interior Features

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

Exterior Features

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

Days on Market

Days on Market: 76

Property Information

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

Price & Status

Price
List Price: $100,000,000Price Per Sqft: $7,597

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: Riverside
School Information
Elementary School: RiversideJr High / Middle School: Eastern

Agent Information

Listing Agent
Listing ID: 125034

Building

Building Area
Building Area: 13163 Square Feet

Lot Information

Lot Area: 2.91 Acres

Mobile R/V

Mobile Home Park
Mobile Home Units: Feet

Miscellaneous

BasementMls Number: 125034
Last check for updates: about 11 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..

Market trends in Greenwich

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.1M
$340KMoM
Sale-to-List Price
102.7%
1.5%MoM
Price per sq ft
$801
$22MoM
Available listings
190
7MoM

Price History for 108 Cedar Cliff Rd

DatePriceEventSource
05/18/2026$100,000,000Listed For SaleGreenwich MLS, Inc. #125034
07/27/1994$7,800,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$206,971
Assessment$17,190,320
Home facts updated by county records

Comparable Sales for 108 Cedar Cliff Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
88 Cedar Cliff Rd, Riverside, CT
0.13
Single-Family Home
$13,250,000
08/15/25
7
9.5
9,416
142 Cedar Cliff Rd, Riverside, CT
0.13
Single-Family Home
$10,250,000
09/12/25
6
7.5
9,258
52 Carriglea Drive, Riverside, CT
0.60
Single-Family Home
$12,900,000
12/29/25
6
7
9,418
43 Jones Park Dr, Riverside, CT
0.70
Single-Family Home
$10,750,000
11/14/25
5
5
6,577
7 Indian Head Rd, Riverside, CT
0.88
Single-Family Home
$7,750,000
07/15/26
6
6
8,364
44 Indian Head Rd, Riverside, CT
0.71
Single-Family Home
$4,650,000
11/05/25
4
5
4,097
247 Riverside Ave, Riverside, CT
1.04
Single-Family Home
$8,300,000
04/06/26
6
8.5
9,485
579 Indian Field Rd, Greenwich, CT
1.20
Single-Family Home
$40,000,000
11/19/25
6
9.5
11,500
35 Club Rd, Riverside, CT
1.05
Single-Family Home
$9,750,000
10/17/25
6
7
8,896

Nearby homes

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Assigned Schools

These are the assigned schools for 108 Cedar Cliff Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Riverside
See Local Highlights
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.
  • Sharon Elkayam
    "It is a friendly community where the kids ride bikes and play together. The schools are good. The kids play in the front yards. "
    0
    Flag
  • Trulia User
    "Very dog friendly. Lots of great places to walk with a dog. Many dog owners. The beach in Old Greenwich is a fun place to meet other dog owners and allow them to play."
    0
    Flag
  • Trulia User
    "I95 is the worst and the Merritt parkway are very difficult to commute on. Good luck if you need to commute during peak times. "
    1
    Flag
  • Sharonelkayam
    "Kid and pet friendly. Nice neighbors and well kept homes. The schools are great. Good area for walking and running. Near trains and shopping area in Old Greenwich. Beach is also a few minutes away."
    1
    Flag
  • Jesselynn G.
    "The elementary school fairs/carnivals, trick or treating, fireworks at the park nothing else in particular but overall a great neighborhood "
    0
    Flag
  • Rebecca
    "People r always out walking their dogs. Cars know they have the right of way and will either slow or go around completely "
    0
    Flag
  • Rebecca
    "Cozy neighborhood feel. Folks say hello when u walk past them. Lots of kids on bikes and dogs on leash"
    0
    Flag
  • Msuppodvm
    "Many special events around families and children. Many resources available for families and kids. Excellent afternoon programs, many sports programs. "
    0
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  • Mirielramos
    "I love my neighborhood is peaceful and quiet, nice place to live, and have all close by, bank, supermarket, drug stores etc"
    0
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  • Mcm.captiva@gmail.com
    "I see lots of dogs being walked. and responsible dog owners cleaning up after their dogs. Some owners having invisible fenced and didn't playing in yards. "
    0
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  • Mcm.captiva@gmail.com
    "neighborhood charity 10K runs. Church carnival. patriotic displays. fireworks in park. outdoors music."
    0
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  • Mcm.captiva@gmail.com
    "I take train to GCT and it is a short walk to METRO North. The commuter trains run very reliably and often."
    0
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  • Kimberly.kois
    "Very family friendly , sporty , safe , neighborhood with great access to public transportation, elementary schools, parks, playground , beach , Old Greenwich town"
    0
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  • Rebecca
    "Close to the water....can walk into town...kids walk or bike to school....unspoken neighborhood watch "
    8
    Flag
  • Sophiecoko
    "Living in a coastal neighborhood is really special. I love seeing the kids biking to the beach without jackets on ready to sail, kayak or paddle board."
    0
    Flag
  • dryfly7
    "Beautiful Dogwood Park Association, 3 minute walk to highly rated North Mianus Elementary School"
    0
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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.
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.