Kathie Lee Gifford is ready to part with the sprawling Connecticut estate where she built a life with her late husband, NFL legend Frank Gifford — and she is aiming high with a staggering $100 million asking price.

The former “Today” show host and longtime television personality has listed Cedar Cliff, her nearly 3-acre waterfront compound in Greenwich’s exclusive Riverside enclave, in what could become one of the priciest residential sales ever recorded in Connecticut, according to a press release from the listing brokerage. 

If the estate sells anywhere near ask, it would rank among the state’s biggest trophy-home deals, trailing only a handful of ultra-luxury transactions including nearby Copper Beech Farm, which traded for roughly $138.83 million in 2023.

The Mediterranean-style mansion sits on a gated peninsula jutting into Long Island Sound, with more than 1,250 feet of shoreline wrapping around the property on three sides. 

The mansion spans over 15,000 square feet and includes eight bedrooms, sweeping lawns, a dock, private beach access, a tennis court, a pool, a spa, a movie theater, a wine cellar and a professional recording studio.

Kathie Lee and Frank Gifford purchased the property in 1994 for $7.8 million while she was co-hosting “Live! With Regis & Kathie Lee.” The estate traces its roots back to the early 1900s and once formed part of a grand compound owned by railroad magnate Henry Francis Shoemaker.

“Had I never gone into show business, I would have become an architect / interior designer,” Gifford told the Wall Street Journal in an interview. “It has been a passion of mine for as long as I can remember.”

The couple transformed the already-impressive estate over the years, adding a major east wing that introduced a new primary suite, a home office, a theater and a wine cellar. They also expanded the property’s entertainment amenities and created spaces for large gatherings overlooking the water.

“We also added a professional recording studio, where I continued my songwriting and broadcasting career,” she said.

The home became a gathering place for celebrities, athletes, television personalities and friends throughout the decades. Gifford recalled nights playing music with Dolly Parton and tennis matches involving Fred Trump and Donald Trump.

“It seemed like we were always celebrating something,” she said.

The estate also served as an extension of her television career. Segments for the “Today” show were filmed on the grounds multiple times, and Gifford hosted Hoda Kotb’s 50th birthday celebration at the property..

The late Regis Philbin and his wife Joy, who also lived in Greenwich, were frequent visitors over the years.

“I spent 15 years professionally with Regis and they changed my life,” she told the Journal, “but then we went on to have a 25-year friendship which went so much deeper afterwards.”

The home’s interiors combine old-world detailing with modern upgrades, featuring soaring ceilings, antique wood flooring, intricate millwork and oversized windows positioned to maximize water views from nearly every room. A three-level elevator connects the residence’s multiple wings.

Outside, the grounds resemble a private coastal resort. A deep-water pier and dock offer direct boating access, while a waterfront tennis court sits beside manicured lawns sloping toward the shoreline. The pool area includes a spa and cabana equipped with a fitness center, a kitchenette, changing rooms and a full bath.

The property also includes stone terraces overlooking Greenwich Cove and Greenwich Point Park, along with rebuilt sun decks, a newly installed terra cotta roof and a whole-property generator system.

According to Gifford, the family initially had no intention of leaving their smaller Greenwich farm until the arrival of their daughter. 

“But God had other plans, and her name was Cassidy,” she said.

When the couple first toured Cedar Cliff, she said the decision happened almost instantly.

“We gave each other what we call the ‘real-estate nod’ and acquired the home,” she said.

Frank Gifford, the Hall of Fame New York Giants star and longtime “Monday Night Football” broadcaster, died in 2015. Kathie Lee later relocated to Nashville in 2019 after departing NBC’s “Today.”

“Frank and I both came from very humble beginnings,” she said.

The couple referred to the edge of the property as “Praise Point,” where they would watch the sunrise and sunset over the Sound.

After Frank’s death, Gifford said the atmosphere of the home fundamentally changed.

“The house that had once seemed so full of life and of laughter and of music had suddenly gone silent to me,” she said.

She described her move to Tennessee as necessary for a fresh start.

“Moving to Nashville was the new beginning that I needed,” she said. “But I never stopped loving Cedar Cliff.”

Now, more than three decades after first buying the estate, she says the moment has finally come to let it go.

“We always knew in our hearts that we would know when it was the right time,” she said.

Listing agent Leslie McElwreath of Sotheby’s International Realty said the estate’s value lies not only in its scale and pedigree, but also in the rarity of its waterfront infrastructure and privacy so close to Manhattan.