Kathie Lee Gifford’s Greenwich Estate Just Listed for $100 Million and It Is One of the Most Extraordinary Properties We Have Ever Seen

Kathie Lee Gifford’s legendary Greenwich estate just listed for $100 million — and it is, without question, one of the most extraordinary properties we have ever seen on Zillow.

Known as Cedar Cliff — a name so iconic it literally defines the road it sits on — this is a 13,163 square foot waterfront mansion perched atop a gated 2.91-acre peninsula in Riverside, Connecticut, with 1,250 feet of direct water frontage and panoramic views stretching from Long Island Sound all the way to the Manhattan skyline. It is currently the most expensive home listed in all of Connecticut.

And it has a recording studio. And a private deep-water dock. And a waterfront tennis court. We are going to need a minute.

📍 108 Cedar Cliff Rd, Riverside, CT 06878
💰 $100,000,000
📐 13,163 sq ft | 2.91-acre gated peninsula
🛏 8 bedrooms | 14 bathrooms
📅 Built 1930
🌊 1,250+ feet of direct Long Island Sound waterfront
🎾 Waterfront tennis court
🎙 Recording studio
🏆 Most expensive listing in Connecticut

The History Behind Cedar Cliff

This property’s story goes back well over a century. The estate 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 name Shoemaker gave his villa, Cedar Cliff, eventually defined the very road on which it stands. Kathie Lee and Frank Gifford called it home for decades, raising their family here while Frank was one of the most recognizable faces in sports broadcasting. It is, in every sense, a storied piece of American history.

The Estate Is Something Else

Cedar Cliff offers eight bedrooms, formal entertaining spaces, a three-level elevator, a recording studio, wine cellar, private theater, and an East Wing with a primary suite and office. Every one of those eight oversized bedrooms is oriented to capture the water views. The interiors blend pre-war craftsmanship with modern refinement — soaring ceilings, intricate millwork, and the kind of detail you simply cannot find in new construction.

Step outside and it only gets better. Outdoor amenities include a deep-water dock, stone pier, waterfront tennis court, pool and spa, cabana with fitness center, and multiple terraces overlooking Greenwich Cove. The sweeping manicured lawn rolls all the way down to the shoreline. The setting is genuinely unmatched on the East Coast.

The Most Expensive Listing in Connecticut

Cedar Cliff is currently the most expensive home being offered in Connecticut. At $100 million for a property with this kind of history, this scale, and this location — a gated peninsula with Manhattan skyline views, 1,250 feet of waterfront, and a legacy that spans over a hundred years — it is easy to understand why.

We have looked at a lot of homes. This one is in a category entirely its own.

Currently listed via Leslie McElwreath 917-539-3654, Sotheby’s International Realty

👉 See the full listing on Zillow