Kathie Lee Gifford has placed her sprawling Connecticut estate on the market for $100 million, marking one of the most expensive residential listings in the state's history. The former television host, who moved to Tennessee after selling her previous home there, is parting with the Riverside property she shared with her late husband, NFL legend Frank Gifford.
The mansion, located in the exclusive Indian Head Association in Greenwich, spans 13,000 square feet and sits on land that once belonged to railroad magnate Henry Francis Shoemaker. Gifford purchased the property in 1994 for $7.8 million and oversaw extensive renovations that transformed it into a Mediterranean-style villa.
A Home with Gilded Age Roots
The estate's history stretches back to the Gilded Age, when the site housed the Cedar Cliff Beach Club in the 1920s. Gifford's renovations preserved that sense of grandeur while adding her personal touch. The result is a residence that feels both historic and intimate, with eight bedrooms and nine bathrooms spread across multiple levels.
During her years there, Gifford hosted a who's who of American culture, including Dolly Parton and Donald Trump. The property became a backdrop for her life after television, a place where she could entertain friends and family away from the cameras.
“This home was my sanctuary,” Gifford has said in interviews. “Every corner holds a memory.”
Waterfront Luxury and Privacy
The listing, handled by Sotheby's International Realty, highlights the estate's waterfront location on Long Island Sound. The grounds include expansive lawns, a pool, spa areas, and outdoor dining spaces designed to take full advantage of the coastal views. The property also offers private access to the Indian Head Association's amenities, including a beach club and tennis courts.
For Gifford, the sale represents the end of an era. She has already established a new home in Tennessee, where she has been focusing on her music and writing projects. The Connecticut mansion, once a hub for her East Coast life, now awaits a buyer who appreciates both its history and its potential.
In the world of celebrity real estate, this listing joins a growing list of high-profile sales. For context, the McDonald's dynasty recently sold a Palm Beach estate for $64.35 million, while Ken Griffey Jr. listed his Windermere lakefront mansion for $27 million. Gifford's asking price, however, places her property in a league of its own for Connecticut.
As the real estate market continues to evolve, this listing serves as a reminder that luxury homes are more than just investments—they are repositories of personal history. For Gifford, the decision to sell was likely bittersweet, but it also signals a new chapter. The question now is who will step into her legacy.
