A look at Kathie Lee Gifford’s $100 million Connecticut home

Former “Today” show host Kathie Lee Gifford is selling her sprawling 13,163-square-foot Connecticut home. The asking price? $100,000,000.

Dubbed “Cedar Cliff,” the Greenwich estate at 108 Cedar Cliff in the Riverside section of town, was once owned by railroad tycoon Henry F. Shoemaker. Kathie Lee Gifford and her late husband, football legend Frank Gifford, purchased the house in 1994 for $7.8 million . The 13,163-square-foot, 29-room estate has eight bedrooms and 14 bathrooms (nine full, five half).

“They added a substantial addition to the house to make it work for their lifestyle,” listing agent Leslie McElwreath of Sotheby’s International Realty said. That addition is the east wing of the house, constructed in the early 2000s, which includes a private theater and wine cellar.

The eight bedrooms are similarly sized and have views of Greenwich Cove. The primary bedroom and two guest bedrooms have a balcony as well. The estate has a greenhouse, a screened porch, a sun room, a tennis court, and a billiards room currently containing Frank Gifford memorabilia. There are 10 fireplaces throughout the house.

Within the 2.91-acre gated peninsula is a spa, pool, and pool house.

McElwreath said “empty nester” Gifford is selling the property because “her children are grown and are married with their own children. Kathie Lee spends most of her time in Tennessee and is no longer using the house full-time.”

The house has a recently installed Ludowici terra cotta roof, sun decks that have been rebuilt, and there is access to a full-property generator as well as a private beach.

McElwreath said there are additional aspects that make this property worth the monstrous price tag.

“The setting is extraordinary. Elevated high above the water with over 1,250 feet of frontage, the property offers the rare combination of commanding panoramic views and direct waterfront access via a private pier and deep water dock,” she said.

McElwreath said the kind of buyer looking at this property is attracted to Greenwich for its high quality of life and proximity to Midtown Manhattan.

”High net-worth buyers do not compromise. They seek exceptional properties in prime locations. Cedar Cliff is a one-of-a-kind opportunity and will attract buyers looking for privacy and resort-like amenities,” McElwreath said.

The task of selling the estate was entrusted to McElwreath by Gifford after McElwreath represented the seller of Copper Beech Farm in Greenwich, which sold for just under $139,000,000 in 2023.

“[Copper Beach] is still the highest sale ever in Greenwich and the state of Connecticut. I plan to use the full resources of Sotheby’s International Realty to find the buyer for Cedar Cliff,” McElwreath said. “I also represented the seller of 100 Field Point Circle, the second highest sale in Greenwich at $50 million. My proven track record, combined with the marketing expertise of Sotheby’s, will prove to be a winning combination.”