Kathie Lee Gifford Just Listed Her Beloved Greenwich Estate For $100 Million (She Bought It In 1994 For $7.8 Million)

Kathie Lee Gifford is ready to part with one of the most meaningful pieces of her life.

The former "Live! With Regis and Kathie Lee" and "Today" host has listed her longtime waterfront estate in Greenwich, Connecticut, for $100 million. If the home sells anywhere near that asking price, it would rank among the most expensive residential transactions in Connecticut history.

That is a staggering number on its own. But it becomes even more remarkable when you consider what Kathie Lee and her late husband, football legend Frank Gifford, paid for the property.

In 1994, the Giffords bought the estate for $7.8 million.

Today, 32 years later, Kathie Lee is asking $100 million.

That is a potential paper gain of $92.2 million before renovations, upkeep, taxes, commissions, and other costs. Put another way, the asking price is nearly 13 times what the couple paid for the home during the height of Kathie Lee's run on "Live! With Regis and Kathie Lee."

The estate, known as Cedar Cliff, is located in the Riverside neighborhood of Greenwich, roughly 40 miles north of New York City. It sits on about 2.9 acres at the tip of a peninsula that juts into Long Island Sound. The property has more than 1,250 feet of water frontage on three sides, plus a private beach, dock, pool, poolhouse, tennis court, and a Mediterranean-style mansion with more than 15,000 square feet of living space. Here is a video tour of Cedar Cliff:

Kathie Lee has owned the home for more than three decades. It was where she and Frank raised their children, Cody and Cassidy. It was where she commuted from during her years on morning television. It was where the couple entertained famous friends, hosted charity events, filmed "Today" segments, and built a family life that mixed old-school show business, sports royalty, faith, music, and waterfront Connecticut glamour.

Now, after moving to Nashville, she says the time has come to sell.

A $7.8 Million Purchase During The Peak Of "Live!"

Kathie Lee and Frank Gifford bought Cedar Cliff in 1994. At the time, Kathie Lee was one of the most famous women on daytime television thanks to "Live! With Regis and Kathie Lee." Frank was already a sports icon: a former New York Giants star, Pro Football Hall of Famer, and longtime broadcaster on "Monday Night Football."

The couple had been living on what Kathie Lee described as a small farm in Greenwich. They had a young son, Cody, and after their daughter Cassidy was born in 1993, they began looking for a larger home on the water.

When they saw Cedar Cliff, they knew.

The property already had extraordinary bones. It dated back to the early 20th century, when it had been part of a larger compound owned by the wealthy Shoemaker family. The main house was built in the 1930s in a Mediterranean style, with white stucco, red roof tiles, and sweeping views of Long Island Sound.

The Giffords bought it for $7.8 million, then spent years making it their own.

What Comes With A $100 Million Greenwich Estate?

Cedar Cliff is not just a large house with a big price tag. Its value is tied to a rare combination of location, frontage, acreage, history, and amenities.

The estate includes:

• A roughly 15,000-square-foot Mediterranean-style mansion
• Eight bedrooms
• About 2.9 acres
• More than 1,250 feet of waterfront
• A private beach
• A deep-water pier and dock
• A swimming pool
• A poolhouse
• A tennis court
• A fitness center built beneath the pool
• A movie theater
• A home office
• A wine cellar
• A professional recording studio
• A prayer garden
• A gazebo and outdoor entertaining spaces

The Home Kathie Lee And Frank Built Together

After buying Cedar Cliff, the Giffords renovated and expanded the estate over many years. They added a three-story east wing with a new primary suite, movie theater, home office, and wine cellar. Kathie Lee also added a professional recording studio, allowing her to continue songwriting and broadcasting work from home.

The estate became more than a trophy property. It was a family home, a work space, and an entertainment venue. Kathie Lee has recalled hosting charity events, screenings, and gatherings with friends including Regis and Joy Philbin, Dolly Parton, Hoda Kotb, and Kevin Costner. Segments of "Today" were also filmed in the backyard.

Frank Gifford died in August 2015 at the age of 84. After his death, Kathie Lee continued living at Cedar Cliff, but the house changed emotionally. What had once been a lively family home filled with music, guests, children, and television friends became much quieter, especially after her children settled in California.

In 2019, after leaving "Today," Kathie Lee moved to the Nashville area and began a new chapter in Tennessee. She held on to Cedar Cliff for years, but she has now decided it is time to let the property go.

The Math Behind The Listing

If Kathie Lee gets the full $100 million asking price, the raw numbers are staggering. She and Frank bought the estate for $7.8 million in 1994. A sale at $100 million would represent a $92.2 million increase and nearly 13 times the original purchase price.

That does not mean she would pocket that entire amount as profit. The Giffords spent heavily renovating the estate, and a property of this size carries enormous costs for taxes, insurance, maintenance, staffing, landscaping, and repairs. A sale would also involve brokerage commissions and closing costs.

Still, the listing shows how dramatically the ultra-luxury Greenwich market has changed. A $7.8 million waterfront mansion was already a major purchase in 1994. Three decades later, rare waterfront estates in Greenwich can be priced like the top homes in Malibu, Manhattan, or the Hamptons.