Kathie Lee Gifford’s Connecticut Home Lists for $100 Million

When seeking an upgrade from a small farm for their growing family over three decades ago, Kathie Lee Gifford and her late husband, Frank, discovered a sprawling waterfront estate in the coastal Connecticut town of Greenwich.

The couple—she a former morning-show host of Today with Kathie Lee and Hoda and Live! With Regis & Kathie Lee, and he an NFL Hall of Famer and Monday Night Football sportscaster—was immediately drawn to the property’s extraordinary scale and distinctive Mediterranean beauty. “We felt as though we were stepping onto the grounds of a European villa,” Kathie Lee said in a People magazine interview. “It was just stunning.”

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The Giffords went on to acquire the place in 1994 for $7.8 million and then embarked upon an extensive renovation project. Most notably, they added a professional recording studio and a three-story east wing featuring a deluxe primary suite, a 20-seat movie theater, an office, and a wine cellar. Now, 32 years later, the property has come to market for a staggering $100 million, with the listing held by Leslie McElwreath of Sotheby’s International Realty, Greenwich Brokerage.

Known as Cedar Cliff and dating back to the early 1900s, the gated estate stands on the historic grounds of railroad magnate Henry Francis Shoemaker’s onetime compound. If it sells for close to the asking price, it will be one of the most expensive homes ever sold in Connecticut. The current record is held by Copper Beach Farm, also in Greenwich, which traded hands in 2023 for almost $139 million.

Perched on a nearly three-acre peninsula jutting into the Long Island Sound, the reimagined residence sits within the Riverside neighborhood’s esteemed Indian Head Association, about an hour northeast of Manhattan. It is anchored by a circa-1930s white stucco and terracotta-roof villa spanning roughly 13,100 square feet with eight bedrooms, nine full bathrooms, and five powder rooms. An elevator services all three levels, which are showcased by antique wood floors, soaring ceilings, detailed millwork, 10 fireplaces, and large windows overlooking the water from almost every room.

The landscaped grounds are a standout feature of the property, with a pool and spa set alongside a pavilion that includes a fitness center, kitchenette, full bathroom, and changing rooms. There’s also a lighted tennis court with a viewing pergola and a series of terraces atop Greenwich Cove and Greenwich Point Park. From there, a grassy lawn descends to more than 1,250 feet of shoreline, complete with a stone pier, a deep-water dock, and private beach access.

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After Frank’s death in 2015, she made a permanent move to Tennessee to focus on her singing and songwriting career, but Kathie Lee’s favorite memories of the home include entertaining friends from Regis and his wife, Joy, to Dolly Parton.

“The house that had once seemed so full of life and of laughter and of music had suddenly gone silent to me,” she told The Wall Street Journal. “Moving to Nashville was the new beginning that I needed. But I never stopped loving Cedar Cliff.”

Click here for more photos of the Greenwich residence.