Connecticut’s Most Expensive Home Lists for $100 Million in Greenwich

Date of Publishing: June 13, 2026

Cedar Cliff Becomes the Most Expensive Home for Sale in Connecticut

A rare piece of Connecticut real estate history has entered the market with a staggering $100 million asking price. Known as Cedar Cliff, the landmark waterfront estate at 108 Cedar Cliff Road in Riverside has officially become the most expensive home currently listed for sale in Connecticut, setting a new benchmark for luxury property across the state.

Aerial front view of Cedar Cliff, Connecticut's most expensive home, overlooking Long Island Sound in Riverside — The iconic Cedar Cliff estate in Riverside, Connecticut, features nearly three acres of waterfront land and panoramic Long Island Sound views.

Positioned on a private 2.91-acre peninsula overlooking Long Island Sound, the Mediterranean-style compound commands more than 1,250 feet of direct waterfront and offers uninterrupted views stretching from Greenwich Harbor to the Manhattan skyline. Elevated above the flood zone and surrounded by water on three sides, the estate occupies one of the most coveted residential settings on the East Coast.

Listed by Leslie McElwreath of Sotheby’s International Realty, Cedar Cliff combines architectural heritage, resort-caliber amenities, and a legacy that spans more than a century.

A Gilded Age Legacy on One of Greenwich’s Finest Waterfront Sites

Long before it became one of Connecticut’s most celebrated private residences, the property formed part of the estate of railroad magnate Henry Francis Shoemaker. The grounds later served as the famed Cedar Cliff Beach Club during the Roaring Twenties, helping establish the shoreline as one of Greenwich’s most prestigious waterfront enclaves.

Aerial view of Cedar Cliff estate on a private waterfront peninsula with tennis court in Riverside Connecticut — Cedar Cliff Waterfront Peninsula Estate in Riverside Connecticut

Today, the estate remains privately tucked away within Riverside’s exclusive Indian Head Association, a coveted waterfront community known for its privacy, beach access, and proximity to Manhattan.

The home itself was originally constructed in 1930 and has been carefully expanded and modernized over the decades while preserving its timeless Mediterranean character. Terracotta rooflines, grand archways, and elegant proportions create an architectural presence rarely found in contemporary luxury construction.

Elegant waterfront sitting room at Cedar Cliff estate featuring panoramic Long Island Sound views in Riverside Connecticut — Large wood-framed windows and French doors connect this waterfront sitting room to Cedar Cliff’s landscaped grounds and sweeping Long Island Sound views.

Formal dining room at Cedar Cliff estate overlooking Long Island Sound and manicured waterfront grounds in Riverside Connecticut — Expansive picture windows frame panoramic water views from the dining room, overlooking Cedar Cliff’s landscaped lawns and private waterfront setting.

Eight Bedrooms Framed by Water Views

Spanning approximately 13,163 square feet, the residence offers eight bedrooms, fourteen bathrooms, and a series of formal and informal living spaces designed to maximize the property’s extraordinary setting.

Luxury primary bedroom at Cedar Cliff estate with panoramic Long Island Sound views in Riverside Connecticut — The waterfront primary suite at Cedar Cliff features floor-to-ceiling water views, private terrace access, and timeless coastal elegance overlooking Long Island Sound.

Luxury bathroom at Cedar Cliff estate featuring a freestanding tub and panoramic Long Island Sound views — A spa-inspired bathroom at Cedar Cliff showcases a freestanding soaking tub framed by sweeping waterfront views across Long Island Sound.

Virtually every major room enjoys sweeping water views. Soaring ceilings, intricate millwork, antique wood flooring, and classic pre-war craftsmanship create an atmosphere of understated elegance. The interiors balance historic charm with modern luxury, resulting in spaces that feel both grand and welcoming.

Elegant waterfront sunroom at Cedar Cliff estate with panoramic Long Island Sound views in Riverside Connecticut — Warm wood detailing and expansive arched windows frame breathtaking Long Island Sound views from one of Cedar Cliff’s waterfront living spaces.

A three-level elevator connects the residence, while a professional recording studio reflects the estate’s history as the longtime home of television personality Kathie Lee Gifford and her late husband, NFL Hall of Famer Frank Gifford. Over the years, the home welcomed numerous notable guests from the worlds of entertainment and sports.

A Private East Wing Adds Modern Luxury

One of the estate’s most significant enhancements arrived in the early 2000s with the addition of a substantial East Wing.

This newer section introduces a luxurious primary suite overlooking the Sound, accompanied by a custom office, climate-controlled wine cellar, and a private theater capable of seating up to twenty guests. The expansion transformed Cedar Cliff into a true modern compound while remaining architecturally consistent with the original residence.

Classic billiards room and private library inside Cedar Cliff estate in Riverside Connecticut — A richly detailed game room combines a private library, custom millwork, and a classic billiards table, reflecting the historic character of Cedar Cliff.

The result is a home equally suited for intimate family living or large-scale entertaining.

Resort Amenities Rival the World’s Finest Coastal Estates

The outdoor experience at Cedar Cliff rivals that of a private luxury resort.

Rear elevation of Cedar Cliff estate featuring landscaped terraces and waterfront gardens in Riverside Connecticut — The rear façade of Cedar Cliff opens to beautifully landscaped terraces, formal gardens, and outdoor entertaining spaces overlooking Long Island Sound.

A deep-water dock and substantial stone pier provide immediate access to Long Island Sound, allowing owners to move seamlessly between estate life and boating excursions. A waterfront tennis court with lighting and pergola offers championship-level play against a backdrop of open water.

Private waterfront tennis court at Cedar Cliff estate overlooking Long Island Sound in Riverside Connecticut — Cedar Cliff’s championship-style tennis court enjoys a spectacular waterfront setting with panoramic views across Long Island Sound.

Near the shoreline, a resort-style swimming pool and spa are complemented by a fully equipped cabana featuring a fitness center, changing facilities, and kitchenette. Multiple stone terraces descend toward the water, while a bluestone bar overlooks Greenwich Cove and the protected landscape of Greenwich Point Park.

Resort-style waterfront pool and cabana at Cedar Cliff estate overlooking Long Island Sound in Riverside Connecticut — The resort-style pool, spa, and waterfront cabana create a private retreat overlooking Long Island Sound at Connecticut’s most expensive home.

The expansive lawns create a dramatic visual connection between the residence and the shoreline, offering a setting capable of hosting events on a scale rarely achievable in the Northeast luxury market.

Manicured waterfront lawn and garden terraces at Cedar Cliff estate overlooking Long Island Sound in Riverside Connecticut — Expansive lawns, formal gardens, and stone terraces create a spectacular waterfront setting at Cedar Cliff with panoramic views across Long Island Sound.

A Trophy Property Less Than an Hour from Manhattan

Few estates combine privacy, waterfront access, and connectivity as effectively as Cedar Cliff.

The property offers private beach privileges, watercraft facilities, and quick access to Westchester County Airport. Midtown Manhattan can be reached in under an hour, making the estate an attractive option for executives seeking a primary residence or weekend retreat without sacrificing accessibility.

Waterfront view of Cedar Cliff estate with terraced gardens overlooking Long Island Sound in Riverside Connecticut — Perched above more than 1,250 feet of shoreline, Cedar Cliff commands panoramic Long Island Sound views from one of Connecticut’s most prestigious waterfront settings.

Its location within Greenwich is particularly significant. Fairfield County has become one of the strongest luxury housing markets in the United States, with Riverside’s 06878 ZIP code ranking among the nation’s most expensive residential areas.

Why Cedar Cliff Matters in the Connecticut Luxury Market

The $100 million asking price places Cedar Cliff in a category occupied by only a handful of trophy properties nationwide.

According to local reports, it currently stands as Connecticut’s most expensive active residential listing, surpassing every other property on the market by a considerable margin. If it approaches its asking price, the transaction would rank among the largest residential sales in Connecticut history.

More importantly, the estate represents something increasingly difficult to replicate: nearly three acres of private waterfront land, extensive shoreline frontage, deep-water access, historic provenance, and proximity to New York City.

For ultra-high-net-worth buyers seeking a generational asset rather than simply a luxury residence, opportunities of this caliber emerge only rarely.

Property Overview
108 Cedar Cliff Road, Riverside, Connecticut 06878