Inside Kathie Lee Gifford’s $100M Greenwich, Connecticut Estate

Kathie Lee Gifford Lists Lavish Greenwich Estate for $100 Million: Unpacking the Iconic “Cedar Cliff”

For decades, we’ve watched Kathie Lee Gifford move from the busy “Today” show studios to her quieter life in Tennessee. Now, she’s back in the Connecticut spotlight, listing her dazzling Greenwich estate, “Cedar Cliff,” for a jaw-dropping $100 million.

This waterfront property has deep roots and a flair for the dramatic. It gives us a rare peek into the luxury that’s surrounded one of America’s most familiar faces.

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A Storied Past and a Luxurious Present

You’ll find the estate at 108 Cedar Cliff, tucked into Greenwich’s sought-after Riverside area. Its history stretches back to railroad tycoon Henry F. Shoemaker.

Kathie Lee and her late husband, Frank Gifford, bought the place in 1994 for $7.8 million. That move set the scene for years of family memories and celebrity moments.

This isn’t your average home. At 13,163 square feet, it’s a showstopper, with 29 rooms that feel both grand and inviting.

Love space? There are eight bedrooms, each one a retreat, and many offer sweeping views of Greenwich Cove. You’ll also find 14 bathrooms—nine full, five half—so privacy and convenience are never an issue.

The original home got a thoughtful update in the early 2000s with a new east wing. The Giffords wanted more room for entertaining, so they added a high-end private theater and a serious wine cellar.

These new touches fit right in with the home’s classic style. The result is a space that feels both historic and fresh.

An Idyllic Peninsula of Unrivaled Waterfront Living

But honestly, the magic of “Cedar Cliff” isn’t just inside. The estate stretches across a 2.91-acre gated peninsula, offering a sense of privacy that’s tough to match.

With over 1,250 feet of water frontage, the views are nothing short of breathtaking. It’s the kind of place where you wake up to the sound of water and end your day with a sunset that never gets old.

Boating fans will appreciate the private pier and deep-water dock. If you’d rather stay on land, there’s a private beach—pretty rare in this neck of the woods.

Amenities Fit for a Star

Outside, the grounds are all about fun and relaxation. There’s something for everyone, whether you want to unwind or host a crowd.

* A greenhouse for anyone with a green thumb or just a love of plants.
* A screened porch—great for summer nights, minus the bugs.
* A sun room that’s perfect for lazy mornings or winding down in the evening.
* A tennis court for a quick match or two.
* A billiards room filled with Frank Gifford’s memorabilia, which adds a personal touch.
* A spa, a sparkling pool, and a pool house that make the place feel like your own private resort.

Inside, you’ll find 10 fireplaces that bring warmth and a sense of coziness to different rooms. The estate recently got a new Ludowici terra cotta roof and rebuilt sun decks for sunny afternoons.

A full-property generator keeps things running smoothly, no matter what.

The Expert Perspective and the Future of “Cedar Cliff”

Listing agent Leslie McElwreath of Sotheby’s International Realty has handled record-breaking sales in Greenwich, including the famed Copper Beech Farm. Now, she’s taking on the challenge of finding a buyer for this extraordinary property.

McElwreath mentions that Kathie Lee Gifford, now an “empty nester” living mostly in Tennessee, is selling because the estate no longer fits her full-time lifestyle.

She believes the substantial asking price makes sense, given the property’s exceptional setting and its rare waterfront access. Greenwich keeps attracting high-net-worth individuals who want both privacy and resort-style amenities, all close to the lively towns of Stamford and cultural spots in New York City.

The price tag might raise eyebrows, but honestly, the mix of history, luxury, and that unbeatable waterfront at “Cedar Cliff” could draw buyers from places as far south as Darien or as picturesque as Old Lyme. This estate stands as a true landmark in coastal Connecticut, just waiting for its next chapter.

Here is the source article for this story: A look at Kathie Lee Gifford’s $100 million Connecticut home

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