Kathie Lee Gifford’s $100 Million Mansion Sale Marks the End of an Era

Kathie Lee Gifford is making headlines again — not for a television comeback or a new entertainment project, but for putting one of Connecticut’s most recognizable celebrity estates on the market for a staggering $100 million.

The former “Today” show host and longtime daytime television icon has officially listed her sprawling waterfront property, known as Cedar Cliff, in Greenwich, Connecticut. The move closes a deeply personal chapter tied to both her legendary television career and her decades-long marriage to late NFL Hall of Famer Frank Gifford.

The estate, located at 108 Cedar Cliff Road in Greenwich’s exclusive Riverside neighborhood, has become one of the most talked-about luxury real estate listings in the United States this year.

A Celebrity Estate With Decades of History

Kathie Lee and Frank Gifford purchased the property in 1994 for $7.8 million, a figure that now looks modest compared to the current asking price. More than three decades later, the estate is being marketed for nearly 13 times what the couple originally paid.

The Mediterranean-style mansion sits on approximately 2.9 acres at the edge of a peninsula overlooking Long Island Sound. The property boasts roughly 1,250 feet of shoreline, giving it a rare combination of privacy, open water views, and resort-style living.

Originally built in the 1930s, Cedar Cliff occupies land once associated with railroad magnate Henry Francis Shoemaker. Over time, the estate evolved into one of the most recognizable private homes in Greenwich.

The property’s name itself carries historical significance.

According to the listing, Cedar Cliff is “a designation that eventually defined the very road on which it stands today.”

Inside the $100 Million Property

The mansion spans approximately 13,163 square feet and contains eight bedrooms, nine full bathrooms, and five half-bathrooms.

But the scale of the estate extends far beyond its bedroom count.

Among the property’s luxury amenities are:

• A professional recording studio
• A 20-seat private theater
• Wine cellar
• Swimming pool and spa
• Fitness center
• Tennis court
• Deep-water dock and private beach access
• Multiple stone terraces overlooking the water
• Elevator servicing multiple floors
• Rebuilt sun decks and a terra cotta roof
• Whole-home generator

A three-story east wing added by the Giffords became one of the home’s defining features. The wing houses the primary suite, home office, theater, recording studio, and wine cellar — all designed with expansive waterfront views.

Sotheby’s International Realty described the property in dramatic terms:

“Cedar Cliff is a singular offering for the most discerning buyer—an incomparable experience of refined luxury, inviting residents and their guests to revel in the natural beauty of one of the finest estates on the East Coast of the United States.”

Another section of the listing adds:

“The grounds rival those of a world-class private resort.”

More Than a Mansion: A Home Filled With Celebrity History

For decades, Cedar Cliff served as both a family residence and an entertainment gathering place.

According to reports, the Giffords hosted countless gatherings on the estate’s expansive lawn, including Hoda Kotb’s 50th birthday celebration. Over the years, celebrity guests reportedly included Dolly Parton, Kevin Costner, Regis Philbin, Kris Jenner, and Donald Trump.

The home also played a central role during Kathie Lee Gifford’s rise as one of America’s best-known television personalities.

From 1985 to 2000, she co-hosted “Live! with Regis and Kathie Lee” alongside Regis Philbin, helping redefine the daytime talk-show format. Later, she became a beloved fixture on NBC’s “Today” show during her 11-year run with Hoda Kotb from 2008 to 2019.

Gifford’s career extended beyond television. She built a reputation as a singer, songwriter, actress, and author while earning multiple Daytime Emmy nominations and eventually a Daytime Emmy win with the “Today” team. In 2021, she received a star on the Hollywood Walk of Fame.

Why Kathie Lee Gifford Is Selling Now

The decision to sell the property appears deeply tied to changes in Gifford’s personal life.

Frank Gifford died in 2015 at age 84. Several years later, Kathie Lee relocated to Tennessee, where her daughter Cassidy lives, and began focusing more heavily on songwriting, writing projects, and a quieter lifestyle outside New York media circles.

The emotional weight of the home reportedly shifted after Frank’s death.

In interviews connected to the listing, Gifford reflected on how the once lively estate eventually grew quieter as her children moved on and family life changed.

Yet she also emphasized her creative connection to the property.

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

That passion became visible through the extensive renovations and expansions carried out over the years.

Could the Sale Break Connecticut Real Estate Records?

The asking price instantly placed Cedar Cliff among the most expensive residential listings in Connecticut history.

Industry observers are now watching closely to see whether the property can approach the state’s record-setting luxury sales figures. A nearby Connecticut estate reportedly sold for nearly $139 million in 2023, setting the benchmark for the region’s ultra-luxury market.

If Cedar Cliff sells anywhere near its asking price, it would become one of the most significant celebrity home transactions on the East Coast in recent years.

The listing is being managed by Leslie McElwreath of Sotheby’s International Realty, Greenwich Brokerage.

The Broader Trend Behind Celebrity Mega-Listings

Gifford’s listing also reflects a broader luxury real estate trend in which celebrities increasingly cash out long-held legacy properties.

Waterfront estates with privacy, large acreage, and proximity to New York City have become especially valuable among ultra-high-net-worth buyers. Greenwich, Connecticut, in particular, has emerged as a magnet for finance executives, media personalities, and wealthy remote workers seeking large estates outside Manhattan.

Properties like Cedar Cliff occupy a rare category because they combine:

• Historic pedigree
• Extensive waterfront access
• Resort-style amenities
• Celebrity ownership history
• Relative proximity to New York City

That combination makes homes like this difficult to replicate — even in the luxury market.

A Symbolic Goodbye to a Television Era

For many longtime television viewers, the sale represents more than a real estate story.

Kathie Lee Gifford’s public identity became intertwined with the Connecticut home during the peak years of daytime television. It was the backdrop to decades of commuting into Manhattan studios, celebrity entertaining, and family life with one of America’s most recognized sports broadcasters.

Now, as Gifford continues her life in Tennessee and focuses on faith-based projects, music, and writing, the sale of Cedar Cliff signals the closing of one of the last remaining physical connections to that chapter of her career.

Whether the property ultimately achieves its ambitious $100 million asking price remains to be seen.

But regardless of the final number, Cedar Cliff has already secured its place as one of the most iconic celebrity homes ever to hit the Connecticut market.