GREENWICH, CONNECTICUT — One of the most iconic waterfront estates in the Northeast has officially entered the market.
Television personality and former Today show host Kathie Lee Gifford has listed her longtime Greenwich residence, known as Cedar Cliff, for $100 million, making it the most expensive home currently available in Connecticut. Perched above Long Island Sound on nearly three private acres, the estate represents more than just a trophy property—it is a deeply personal family compound shaped over three decades by Kathie Lee and her late husband, NFL Hall of Famer and broadcasting legend Frank Gifford.
Purchased in 1994 for $7.8 million, the waterfront estate underwent extensive renovations and expansions under the Giffords’ ownership, evolving into one of the most significant residential offerings in Greenwich’s ultra-exclusive luxury market.
According to information reviewed by California Luxury Houses, the Mediterranean-inspired compound spans approximately 13,163 square feet and offers an extraordinary 1,250 feet of direct waterfront frontage overlooking Long Island Sound, with distant views stretching toward the Manhattan skyline.
A Rare Waterfront Legacy Estate in Greenwich
Waterfront properties of this scale and prominence rarely become available in Greenwich, a community long recognized as one of the most prestigious residential markets in the United States.
Situated on approximately 2.91 acres, Cedar Cliff occupies a commanding position above the shoreline, combining privacy, panoramic water views, and deep-water boating access—an increasingly rare combination along the Connecticut coast.
“Large waterfront compounds with this level of frontage are exceptionally scarce, even in Greenwich,” listing agent Leslie McElwreath told California Luxury Houses. “The estate offers a combination of scale, privacy, and direct water access that would be incredibly difficult to recreate today.”
Over the years, the Giffords transformed the residence far beyond its original footprint, commissioning major improvements that included a new residential wing housing a private theater, wine cellar, executive office, and an expansive waterfront primary suite.
The result is a multi-generational estate equally suited for large-scale entertaining, family gatherings, and private coastal living.
Designed Around Long Island Sound
While many luxury homes feature water views, Cedar Cliff was clearly designed to celebrate its waterfront setting at every opportunity.
Throughout the residence, oversized windows frame ever-changing vistas of Long Island Sound. Formal entertaining spaces, intimate lounges, and private living quarters are all positioned to maximize natural light and water views.
A dramatic living room serves as one of the home’s architectural centerpieces, where floor-to-ceiling windows wrap around the curved waterfront façade. Rich wood detailing and sophisticated finishes create a warm atmosphere while ensuring the surrounding scenery remains the focal point.
Nearby, the dining room continues the connection to the outdoors, pairing panoramic waterfront views with elegant yet relaxed design elements intended for both formal occasions and family celebrations.
“The home was thoughtfully expanded over many years,” McElwreath explained in comments shared with California Luxury Houses. “Every major addition was designed to strengthen the relationship between the residence and its extraordinary waterfront setting.”
Traditional millwork, custom detailing, antique flooring, and handcrafted finishes appear throughout the home, reinforcing its timeless character while maintaining a high level of sophistication.
Spaces That Reflect a Remarkable Family Legacy
Beyond its architectural appeal, Cedar Cliff tells the story of a family whose influence spanned television, professional sports, and American popular culture.
One of the home’s most distinctive spaces is a richly detailed billiards lounge dedicated to Frank Gifford’s extraordinary career. Memorabilia from his years with the New York Giants, broadcasting achievements, awards, and personal keepsakes are thoughtfully displayed throughout the room.
Elsewhere, a wood-paneled library offers a quieter retreat for reading and conversation, while a screened waterfront porch provides one of the estate’s most inviting gathering spaces.
California Luxury Houses reached out for additional comment regarding the property’s historical significance to the Gifford family but did not receive a response before publication.
The primary suite occupies a privileged position overlooking the water and includes a private waterfront terrace, spa-inspired bathroom, and expansive sleeping quarters designed to capture uninterrupted views from sunrise to sunset.
“This is a home that has been genuinely lived in and loved,” McElwreath told California Luxury Houses. “Every room reflects decades of family memories while still offering the amenities expected in a world-class luxury estate.”
Resort-Style Grounds With Deep-Water Access
Outside, the estate unfolds across manicured lawns, stone terraces, mature gardens, and a collection of recreational amenities more commonly associated with private resorts.
A curved swimming pool and spa overlook the Sound, accompanied by a Mediterranean-style pavilion designed for outdoor entertaining. Nearby, a waterside gazebo and shoreline bar create additional gathering spaces that embrace the property’s unique waterfront setting.
The estate’s full-size tennis court enjoys sweeping water views, while the surrounding grounds provide multiple locations for large events, private celebrations, and family recreation.
Perhaps the most significant amenity is the property’s deep-water dock and substantial stone pier.
Extending directly into Long Island Sound, the private marine facilities can accommodate larger vessels and provide immediate access to some of the Northeast’s most desirable cruising destinations.
“Boating enthusiasts immediately recognize the value of the dock and waterfront infrastructure,” McElwreath noted to California Luxury Houses. “Combined with the privacy and acreage, it creates a lifestyle opportunity rarely seen in this market.”
Why Greenwich Continues to Attract America’s Wealthiest Buyers
For decades, Greenwich has remained one of the premier luxury enclaves in the United States.
Residents enjoy proximity to New York City while benefiting from expansive estates, private country clubs, yacht clubs, elite schools, fine dining, luxury shopping, and a highly regarded quality of life.
The town’s Gold Coast location has long attracted business leaders, entertainers, professional athletes, hedge fund executives, and international buyers seeking both privacy and accessibility.
Properties with substantial waterfront frontage remain among the most coveted assets within the Greenwich real estate market, particularly those offering deep-water access and resort-caliber amenities.
A New Chapter for Cedar Cliff
Since leaving NBC’s Today show in 2019, Kathie Lee Gifford has increasingly focused her life and professional activities in Nashville.
At the same time, Cedar Cliff remains deeply connected to the legacy of Frank Gifford, whose presence is woven throughout the estate’s architecture, memorabilia collections, and decades of family history.
For a future owner, however, the opportunity extends well beyond celebrity provenance.
Cedar Cliff represents one of the most significant waterfront estates currently available anywhere in the Northeast—a rare combination of architectural elegance, boating access, resort amenities, and historical importance within one of America’s most prestigious residential communities.
With a $100 million asking price, the estate is not merely setting a new benchmark for Greenwich real estate—it is redefining the upper limits of Connecticut’s luxury housing market.