Kathie Lee Gifford has listed her Riverside, Connecticut, estate — known as Cedar Cliff — for $100 million, putting the 13,163-square-foot waterfront home on the market as the priciest dwelling currently offered in Greenwich.
The listing, held by Leslie McElwreath of Sotheby’s International Realty, promotes an eight-bedroom house with nine full baths and five partial baths sitting on nearly three acres in Riverside’s Indian Head Association. The property offers around 1,250 feet of direct water frontage and rests on a secluded road; all eight bedrooms look out over the water.
Built in 1930 and originally named Cedar Cliff by its first owner, a shoemaker, the estate was bought by Gifford and her husband Frank Gifford in 1994 for $7.8 million. The couple renovated and expanded the home, adding a new wing with a movie theater, wine cellar, primary suite and home office. The property also includes an elevator, a private recording studio, a deep-water dock, a pool and spa, a private tennis court and a fitness center.
Gifford described her additions in her own words: "We also added a professional recording studio, where I continued my songwriting and broadcasting career." She recalled entertaining there, saying, "I hosted Hoda’s 50th birthday party on our patio with our Today show family." The listing frames Cedar Cliff as "a singular offering for the most discerning buyer" and calls it "a Mediterranean villa of unrivaled pedigree and commanding presence."
The selling price — roughly thirteen times what the Giffords paid in 1994 — positions the estate as the most expensive home on the Greenwich market, according to the listing presentation and public market tallies. The sheer scale of water frontage, the number of bedrooms with waterfront views, and the collection of leisure amenities are the listing’s chief weighty facts; they are what agents will point to when courting ultra-high-net-worth buyers who prize both privacy and scale.
Context for the sale is compact but personal. After Frank Gifford died in 2015 and Kathie Lee left the Today show in 2019, she moved to Nashville. In interviews and remarks tied to the listing, she has been candid about how those changes affected her relationship with the house: "The house that had once seemed so full of life and of laughter and of music had suddenly gone silent to me," she said. Yet she has also said, "I never stopped loving Cedar Cliff."
That mixture of attachment and distance is the story’s tension. The estate is loaded with the kind of private production and entertainment spaces that made it a hub for celebrity gatherings — guests over the years included her Today colleagues and other notable figures — but Gifford’s life has since moved to another city and another rhythm. She described the move as "the new beginning that I needed," adding that after years tied to the property, it felt like "the right time" to sell.
Listing the house at $100 million tests whether demand for an exceptionally large Greenwich waterfront parcel with celebrity provenance will meet a correspondingly exceptional price. The facts are simple: a 13,163-square-foot, eight-bedroom home built in 1930 on nearly three acres with around 1,250 feet of water frontage and a catalog of rare amenities is now on the market, offered by Sotheby’s through Leslie McElwreath.
Why list now? The answer Gifford herself gives is clear: personal transition and a desire to begin a new chapter. "It seemed like we were always celebrating something," she said of the house’s years as a social center; choosing to sell was part practical and part emotional — a decision she framed as both an acknowledgement of loss and a move toward the future. Whether a buyer will pay a sum that cements Cedar Cliff as Greenwich’s record estate remains to be seen; for now, Gifford has put the property where its scale, history and provenance can find a new owner.
