Kathie Lee Gifford is selling Cedar Cliff, the Riverside waterfront estate she owned with her late husband, Frank Gifford, for $100 million, putting one of Greenwich’s more distinctive private properties before a small group of buyers able to compete at the top of the national housing market.
The Giffords bought the estate in 1994 for $7.8 million. Gifford, who moved to Nashville, Tenn., is ready to part with the property after years of family ownership. Cedar Cliff sits on roughly 2.9 acres in Riverside, with a large Mediterranean-style house from the 1930s, eight bedrooms and more than 15,000 square feet.
Leslie McElwreath of Sotheby’s International Realty is marketing the property. McElwreath, who handled the $138.83 million sale of Copper Beech Farm, the Connecticut residential record, said Cedar Cliff belongs in a narrow category because it combines a gated peninsula, direct waterfront, private association setting, dock, beach and long ownership by one prominent family.
“The valuation reflects an extraordinary convergence of attributes that would be nearly impossible to replicate today,” McElwreath said. “Foremost among them is the land itself: nearly three private acres set on a gated peninsula with more than 1,250 feet of direct waterfront.”
The land is only the first argument for the price. Cedar Cliff includes rolling lawns, a pool, pool house, tennis court, stone terraces, sun-filled patios, a spa, a deep-water dock and a private beach. Those elements are not unusual one by one in Greenwich luxury listings. Their combination on a peninsula in Riverside is the rarity McElwreath is asking buyers to value.
McElwreath described Cedar Cliff as “nestled within one of Riverside’s premier residential enclaves” inside the Indian Head Association. She said the home’s position allows water views from almost every window and gives the property both sunrise and sunset exposures, a geographic advantage that becomes part of the estate’s appeal.
“I know of no other property in the area that enjoys such a singular and extraordinary setting—where panoramic water views, unmatched privacy, and the beauty of both sunrise and sunset come together in such a rare and captivating way,” McElwreath said.
The house gives the land a second selling point. McElwreath described the residence as a Mediterranean-style villa with an elevator, professional recording studio, wine cellar, home theater and an East Wing anchored by a primary suite. The Giffords expanded and maintained the home for family life, entertaining and creative work.
“Meticulously maintained and thoughtfully expanded by Kathie Lee and Frank, the residence blends an elegant, timeless Mediterranean façade with a warm, inviting interior designed for both relaxed family living and sophisticated entertaining,” McElwreath said.
The Giffords renovated the house over time and added a three-story wing. The property was a setting for charity events, television appearances and private gatherings during the family’s years there. The home’s public aura came through two careers: Frank Gifford’s life in football and broadcasting, and Kathie Lee Gifford’s long run on national morning television.
Frank Gifford played for the New York Giants, later became a football broadcaster and was inducted into the Pro Football Hall of Fame in 1977. Kathie Lee Gifford became known nationally through her years with Regis Philbin and later Hoda Kotb. Their shared history at Cedar Cliff gives the listing name recognition, but McElwreath said the marketing should not lean too heavily on celebrity.
“The celebrity connection is certainly meaningful, but it is not the primary story,” McElwreath said. “Kathie Lee and Frank Gifford are deeply admired, and their long stewardship contributes to the home’s legacy. However, the true focus remains on the property itself—its incomparable setting, architectural significance, and rarity.”
Cedar Cliff’s history reaches earlier than the Gifford years. The estate was part of a Shoemaker family compound in the early 20th century, placing it within a longer chapter of Riverside waterfront ownership. That older provenance gives the sale local significance beyond its asking price.
“Carefully stewarded by the Gifford family for decades, the estate carries with it a sense of history, legacy, and cultural significance,” McElwreath said. “Its connection to Kathie Lee and Frank Gifford adds an intangible layer of emotional resonance that transcends real estate alone.”
The listing arrives as Greenwich continues to occupy a rare position in the ultra-luxury market. McElwreath said today’s buyers at this level are looking beyond square footage. They want privacy, architectural integrity, lifestyle, prestige and a form of scarcity that cannot be produced by new construction alone.
“Today’s luxury buyer is more sophisticated, and discerning than ever before,” McElwreath said. “They are no longer simply purchasing a residence; they seek privacy, lifestyle, prestige, and assets of genuine scarcity that cannot be replicated.”
For Greenwich residents, the sale places a familiar name beside a larger question about the future of legacy estates. Large waterfront properties often remain in families for generations, away from the public market. When they surface, they offer a measure of how buyers value land, privacy and history in a town where all three are increasingly scarce. It also creates a practical test of how much buyers will pay locally for a private site that cannot be recreated in the current Greenwich real estate market cycle.
“Cedar Cliff is more than a notable listing; it is an important moment in Greenwich real estate,” McElwreath said. “Properties of this caliber are rarely made available to the public.”
A sale near the asking price would place Cedar Cliff among Connecticut’s most significant residential transactions. It would also reinforce the premium attached to Greenwich waterfront property when acreage, views, privacy and provenance align. McElwreath said the Gifford family’s role in the property is part of that value, but not the whole of it.
“After decades of thoughtful stewardship by the Gifford family, Cedar Cliff is ready for its next chapter,” McElwreath said.
