Kathie Lee Gifford’s Connecticut Estate in Greenwich Lists for $100M

This article takes a look at Cedar Cliff, the waterfront Greenwich estate once owned by Kathie Lee Gifford and her late husband Frank Gifford. It digs into the home’s storied past, its luxury renovations, and the current listing price that’s turning heads in Connecticut’s high-end real estate scene.

From its Mediterranean flair to a dramatic pier and private beach, Cedar Cliff has become one of Fairfield County’s most buzzed-about properties. There’s a reason neighbors keep talking about it.

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A Greenwich Icon: Cedar Cliff’s pedigree and architecture

Cedar Cliff rests on nearly three acres at the tip of a peninsula in Greenwich’s Riverside neighborhood. It’s tucked inside the private Indian Head Association.

The villa’s history stretches back to the early 1900s, once part of railroad magnate Henry Francis Shoemaker’s estate. Its white stucco and terracotta roof give it that classic Mediterranean look—timeless, honestly.

Perched above Greenwich Cove, Cedar Cliff was always meant to impress. Water views fill almost every room, catching the eye of buyers from Connecticut and beyond.

Origins and design

The estate’s architecture blends old-school charm with modern comfort. Built on three levels, the home’s big windows frame the Long Island Sound instead of a city skyline.

Its Riverside location drops Cedar Cliff right into a cluster of Connecticut towns known for luxury—Norwalk, Darien, and just a quick drive to Stamford or New Canaan.

Renovation and expansion

Things really changed after Kathie Lee and Frank Gifford bought the place in 1994 for $7.8 million. They took on a major renovation, adding a three-story east wing with a deluxe primary suite, a 20-seat movie theater, a private office, a wine cellar, and even a professional recording studio.

Now, the home covers about 13,100 square feet. There are eight bedrooms, nine full baths, and five powder rooms spread across three floors, all connected by an elevator.

Interior splendor and amenities

Step inside and you’ll find antique wood floors, soaring ceilings, and detailed millwork. Ten fireplaces anchor the living spaces, while big windows pour in natural light and those signature water views.

Key features at a glance

Eight bedrooms and nine full bathrooms, plus five powder rooms
Three-level layout with an elevator for easy movement
Three-story east wing including a primary suite, a 20-seat theater, a recording studio, and a wine cellar
Formal living spaces and casual lounges surrounded by water views
Terraces and expansive grounds overlooking Greenwich Cove

Grounds, waterfront living, and recreation

The grounds are designed for outdoor living and sports. There’s a pool and spa with a pavilion that includes a fitness center, kitchenette, full bath, and changing rooms. It’s basically a retreat for wellness and entertaining.

A lighted tennis court with a viewing pergola begs for daytime matches or evening games, and the terraces give you plenty of spots to soak in the coastline.

The lawn stretches out to more than 1,250 feet of shoreline. It ends at a stone pier and a deep-water dock, with private beach access for lazy summer days or water adventures.

The setting feels exclusive, but it’s still close to Connecticut towns like Westport, Fairfield, and Wilton, with all their top-notch amenities within reach.

History, market context, and what’s next

Frank Gifford died in 2015, and after that, Kathie Lee Gifford moved to Tennessee. Still, Cedar Cliff stands as a symbol of their life together in Connecticut’s luxury scene.

The estate now sits on the market with Sotheby’s for $100 million. If it gets anywhere near that price, it’ll rank among the state’s most expensive home sales.

Greenwich keeps drawing buyers who want high-end waterfront homes. Folks from nearby cities like Norwalk, Darien, Stamford, and New Canaan, plus those from Fairfield County—think Shelton, Bridgeport, Wilton—keep their eyes on this market.

Cedar Cliff isn’t just another house. It’s a kind of measuring stick for what people expect from coastal luxury around here.

If you’re watching Connecticut real estate, whether you’re serious about buying in Darien or New Canaan or just like following the buzz, Cedar Cliff keeps popping up as a benchmark for waterfront living in the state.

Here is the source article for this story: Kathie Lee Gifford’s Connecticut Home Lists for $100 Million

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