Greenwich, Connecticut’s luxury market has been on fire over the past year, and Kathie Lee Gifford is looking to cash in on the action.
The former “Today” show host this week listed her waterfront estate at 108 Cedar Cliff in Riverside for a whopping $100 million — nearly 13 times what she and her late husband, former New York Giants player and sportscaster, Frank Gifford, paid for it in the early 1990s.
If the sale closes for that price, it would be among the most expensive deals ever achieved in the affluent suburb, long known for its popularity with wealthy commuters to New York City. Just three years ago, another estate in the area, known as Copper Beech Farm and sold by an LLC linked to billionaire Ray Dalio, set a new state record when it sold for close to $139 million.
While not unprecedented, Gifford’s asking price is likely aspirational. While the eight-bedroom mansion sits on a 3-acre lot with sweeping views of the Long Island Sound and the Manhattan skyline, a buyer interested in the property will likely tear down the existing Mediterranean-style home, according to Megan Sullivan, who recently joined Douglas Elliman as an individual agent after leading one of the region’s top teams at Sotheby’s International.
“There are just not that many properties in Greenwich that command that level, and this is not one of them,” Sullivan said.
She added that she expected the property to trade closer to $40 million based on other recent deals. Gifford’s listing broker, Sotheby’s International’s Leslie McElwreath, defended the price to the Wall Street Journal, arguing the property’s location and water access, including a pier, dock and private beach, justified the nine-figure ask.
Even if Gifford misses the mark, it’s hard to fault her for trying, given the Greenwich market’s momentum. Last year, 39 homes traded for more than $10 million, up almost double from the previous year, said Sullivan, who just represented the buyer in the $10.4 million sale of a five-bedroom abode that once belonged to Starwood Capital’s Barry Sternlicht.
But all that activity has wiped out much of Greenwich’s inventory, echoing a common problem across many of the region’s luxury markets. Sullivan said there are only about 100 to 105 homes on the market now, significantly fewer than the 600 to 700 listings during the spring market before the pandemic.
“There’s never, ever been a market like this on so many different levels,” Sullivan said.
Not so fast…
The Upper East Side townhouse market had a banner first quarter.
Deals for homes in the neighborhood totaled close to $283 million during the first three months of the year, up 80 percent compared to the same period in 2025, according to Leslie J. Garfield’s quarterly report.
The area’s sales volume was the highest in Manhattan, though it fell short of its fourth-quarter number, at $326 million in sales. The average sale price rose 70 percent to $16.6 million, while the number of transactions during the period, 17, remained on par with the year-ago numbers.
The report credits the uptick to several notable trades in the neighborhood last quarter, including the $47 million deal for billionaire Ron Perelman’s townhouse at 36 East 63rd Street.
Another big townhouse deal could be on the horizon. Earlier this month, the family of the former Treasury Secretary Steve Mnuchin listed their townhouse at 45 East 78th Street for $35 million.
NYC Deal of the Week
The most expensive sale to hit the city rolls this week was for a co-op at 775 Park Avenue, which traded to a trust tied to financier James Sterne for $16.3 million. The Upper East Side co-op was sold by Thomas Edelman, co-founder of an energy private equity firm, and his wife, philanthropist Ingrid Edelman.
Unit 6/7C, which hit the market in September asking $18 million, spans roughly 5,000 square feet and has five bedrooms and five bathrooms. It also features 11-foot ceilings, a wood-burning fireplace and an eat-in kitchen.
Brown Harris Stevens’ John Burger had the listing.
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