Kathie Lee Gifford Lists Connecticut Estate $100M After Nashville Move

Kathie Lee Gifford’s Cedar Cliff estate in Greenwich just hit the market for $100 million. That’s a jaw-dropping price tag, and it’s putting a spotlight on Connecticut’s luxury coastal real estate scene.

The 13,100-square-foot Mediterranean-style manor sits on almost three acres. There’s private water frontage on Long Island Sound, a secluded beach, and a dock—easily making it one of the most buzzed-about properties in the state.

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Buyers from New York and all along the Shoreline seem to be eyeing these kinds of waterfront homes, from Greenwich to Bridgeport and beyond.

Greenwich’s Cedar Cliff estate hits the market for $100 million

The estate centers on a 1930s home that Kathie Lee Gifford and her late husband Frank Gifford renovated from top to bottom. They also added an East Wing, which has a movie theater, a wine cellar, a primary suite, and a home office.

Inside, you’ll find formal entertaining spaces, a sunroom, and a wood-paneled game room with framed football jerseys. The design really tries to blend timeless elegance with modern comfort, which is what most Connecticut buyers want in Greenwich’s fanciest neighborhoods.

If you’re into boating or just love the ocean, the 1,250 feet of direct water frontage is a real highlight. There’s a private beach and a deep-water dock too.

Step outside and you’ll find a swimming pool, spa, and a seaside cabana with a fitness center and a kitchenette. There’s even a lit tennis court with a pergola, plus several terraces and balconies that look out over Long Island Sound.

The landscaping? It’s about as close to resort-quality as you can get. The grounds are private and sit high enough to avoid flood risks, all while offering those sweeping, postcard-worthy views.

Exclusive features that set Cedar Cliff apart

East Wing with a movie theater, wine cellar, primary suite, and home office

Professional in-home recording studio for Kathie Lee Gifford’s music and broadcasting work

Formal entertaining rooms, sunroom, and a game room with football memorabilia

Seaside cabana, fitness center, and kitchenette for easy poolside living

Private beach, deep-water dock, and 1,250 feet of Long Island Sound frontage

Outdoor luxuries: pool, spa, tennis court, terraces, and balconies

Privacy and raised grounds above flood zones with carefully manicured landscaping

Privacy, water frontage and a Greenwich landmark

Cedar Cliff stands out for its quiet, ultra-exclusive setting—something Greenwich buyers really crave. The property’s elevation gives it a secluded feel, yet it’s still close to all the town’s best spots.

The home’s renovations, along with its rich history (once owned by railroad magnate Henry Francis Shoemaker and the namesake for Cedar Cliff Road), add a layer of story that appeals to buyers who care about heritage and function. The listing points out that the house is perfect for big events, but you can still escape from the city whenever you want.

Kathie Lee Gifford’s Connecticut chapter and the sale timeline

Gifford has talked about her quieter life in Connecticut after Frank passed in 2015, saying it changed her family’s priorities. She moved to Nashville in 2019, and only decided to sell when it felt right.

Their son Cody and his wife lived in the Greenwich estate for a bit after moving back East in 2021—a time Kathie Lee called joyful—before the family decided to list the property. Leslie McElwreath of Sotheby’s International Realty is handling the sale, and Cedar Cliff now holds the title of the most expensive home on the Greenwich market.

A Connecticut luxury market snapshot: eight towns to watch

Cedar Cliff anchors Greenwich’s pinnacle price range. But several nearby towns keep drawing strong buyer interest in today’s market.

Along the coast, Darien, New Canaan, and Westport stand out for their top-tier schools and private, move-in-ready luxury homes.

Stamford and Norwalk have shown surprising resilience. Buyers who want water access and city perks keep these towns on their radar.

Further south, Fairfield and Bridgeport (with some pockets of high-end listings) round out the shoreline market. Waterfront living still drives much of the demand here—no surprises there, honestly.

Across Connecticut, from Greenwich to New Haven, buyers chase properties that blend refined design with a beach-and-boating lifestyle. It’s easy to see why these towns stay in the spotlight.

Here is the source article for this story: Former ‘Today’ Host Kathie Lee Gifford Lists Her Longtime Connecticut Estate for $100 Million—7 Years After Relocating to Nashville

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