Television icon Kathie Lee Gifford has placed her waterfront Greenwich estate on the market with an asking price of $100 million. The property, located in the exclusive Riverside neighborhood, spans nearly three acres and features 13,163 square feet of living space. Leslie McElwreath of Sotheby’s International Realty holds the listing for the historic mansion known as Cedar Cliff. The estate boasts eight bedrooms, nine full bathrooms, and five partial bathrooms, with every bedroom offering direct water views.
Built in 1930, the property was originally commissioned by a shoemaker who christened it Cedar Cliff. The estate’s prominence grew to such significance that the road itself eventually adopted the property’s name. Today, Cedar Cliff sits on a secluded street within Riverside’s prestigious Indian Head Association, one of Connecticut’s most sought-after residential enclaves.
Extensive waterfront features and entertainment spaces
The estate commands approximately 1,250 feet of direct water frontage along Long Island Sound. Meticulously maintained lawns sweep down to the shoreline, creating an ideal setting for large-scale entertaining. The property includes a deep-water dock capable of accommodating substantial vessels, appealing to boating enthusiasts. An outdoor pool and spa complex provides additional recreational amenities, while a private tennis court offers athletic opportunities without leaving the grounds.
Inside the main residence, an elevator services all floors, ensuring accessibility throughout the expansive home. A private recording studio reflects Gifford’s musical background and creative pursuits. The fitness center allows residents to maintain workout routines in complete privacy. According to the listing description, Cedar Cliff represents “a singular offering for the most discerning buyer—an incomparable experience of refined luxury, inviting residents and their guests to revel in the natural beauty of one of the finest estates on the East Coast of the United States.”
Distinguished career in television and entertainment
Gifford established herself as a household name through decades of morning television success. She co-hosted “Live! with Regis and Kathie Lee” alongside Regis Philbin from 1985 to 2000, earning widespread recognition and numerous accolades. After stepping away from that program, she returned to morning television in 2008, co-hosting the fourth hour of NBC’s “Today” show with Hoda Kotb. That partnership continued for eleven years until her departure in 2019.
Born Kathryn Lee Epstein on August 16, 1953, in Paris, France, Gifford spent her early childhood abroad while her father served in the U.S. Navy. The family later relocated to Maryland, where she developed her passion for music and performing. Before pursuing television, Gifford cultivated a career as a singer and songwriter, interests she maintained throughout her broadcasting years.
Awards and industry recognition spanning multiple decades
- Multiple Daytime Emmy Award nominations for her television work
- Daytime Emmy win as part of the “Today” show team
- Induction into the prestigious Broadcast & Cable Hall of Fame
- Hollywood Walk of Fame star awarded in 2021
- Recognition as both a television personality and musical artist
Her multifaceted career encompassed not only hosting duties but also songwriting, acting, and authorship. Gifford wrote several books and composed music for various projects, demonstrating versatility beyond her television persona. Her contributions to daytime television helped define the format for morning talk shows, influencing countless programs that followed.
Greenwich real estate market context
The $100 million asking price positions Cedar Cliff among Connecticut’s most expensive residential offerings. Greenwich has long attracted wealthy executives, celebrities, and finance professionals due to its proximity to New York City and its reputation for privacy and exclusivity. The town’s waterfront properties command premium prices, particularly those within gated communities like the Indian Head Association.
Connecticut’s Gold Coast has seen fluctuating luxury real estate values in recent years, with waterfront estates experiencing particular volatility. Properties exceeding $50 million represent rare transactions in the market, requiring international buyers or ultra-high-net-worth individuals. The 1930 construction date adds historic character while the extensive renovations and modern amenities ensure contemporary comfort standards.
Property amenities designed for luxury lifestyle
The estate’s three-acre footprint provides substantial privacy despite its proximity to Greenwich’s commercial center. The manicured grounds require professional maintenance but offer unparalleled outdoor entertaining possibilities. The combination of formal gardens, waterfront access, and recreational facilities creates a resort-like atmosphere within a private residential setting.
The deep-water dock accommodates yachts and provides direct access to Long Island Sound, connecting residents to broader maritime destinations. The tennis court meets regulation standards for serious players while the fitness center includes professional-grade equipment. These amenities reduce the need for country club memberships or external recreational facilities, offering complete self-sufficiency within the estate’s boundaries.