Kathie Lee Gifford Lists Her Iconic Connecticut Estate and Real Estate Experts Say It Could Break Records
There is only one home listed at $100 million in Connecticut right now. It sits on the tip of a peninsula, with water on three sides, and it has been in the same family for 32 years.
Kathie Lee Gifford just put Cedar Cliff on the market. And the number she is asking is unlike anything this state has ever seen at closing.
This is not just a celebrity real estate story. It is a statement.
The House That Took 32 Years to Let Go
Kathie Lee and her late husband Frank Gifford bought the estate in 1994 for $7.8 million. That is nearly a 13-fold increase to where it stands today.
The property sits in Riverside, Greenwich, on a 2.91-acre gated peninsula at 108 Cedar Cliff Road.
The main house is 13,163 square feet of Mediterranean-style architecture with 8 bedrooms, 9 full bathrooms, and 1,250 feet of waterfront along the Long Island Sound, views stretching toward the Manhattan skyline included.
The Giffords renovated extensively after buying it. They added a three-story east wing with a 20-seat movie theater, a professional recording studio, a wine cellar, a primary suite, and a home office, all overlooking the water.
Kevin Costner, Dolly Parton, Regis Philbin, and Donald Trump all walked through those doors at various points.
Frank passed away in August 2015. Kathie Lee left the Today show in 2019 and moved to Nashville. Her kids settled in California. She held onto this house for 7 more years after all of that.
That one detail tells you more about what this place meant than any listing description can.
$100 Million. $7,600 Per Square Foot. No Comparable in the State.
The listing is held by Leslie McElwreath of Sotheby’s International Realty, Greenwich Brokerage. That name is worth pausing on.
McElwreath also held the listing on Copper Beech Farm, the 50-acre Greenwich estate that sold in August 2023 for $138.8 million, the highest residential sale in Connecticut history. No competitor article has pointed this out.
According to reporting on this listing, at $100 million on 13,163 square feet, the price works out to roughly $7,600 per square foot.
The next most expensive home currently listed in Connecticut sits at $75 million in Stamford. There is a significant gap between Cedar Cliff and everything else on the market right now.
Kathie Lee is not taking a shot in the dark here. She hired the one agent in Connecticut who already knows what nine-figure buyers look like.
Why the Greenwich Market Makes This Less Crazy Than It Sounds
A lot of people see $100 million and assume the price is ego. The market data tells a different story.
In 2025, 38 properties sold for $10 million and over in Greenwich, compared to just 17 in 2024, an increase of over 117% in a single year. The median sale price in Greenwich has gone from $1.95 million in 2020 to $3.25 million as of late 2025.
This is not a sleepy suburban market. Greenwich is the most expensive real estate corridor in Connecticut, and demand for ultra-luxury inventory is outpacing supply with no sign of slowing.
One local market expert put it plainly: “In order for someone to move here, someone else has to move out or pass away. So there’s really no more room,” said Mark Pruner, sales executive at Compass.
Cedar Cliff is not just another Greenwich estate. It is a peninsula. 1,250 feet of water frontage on three sides. Manhattan visible from the water. The kind of privacy that does not get built anymore.
For anyone tracking high-end real estate moves like this one in real time, the WhatsApp channel is worth bookmarking. It covers listings, sales, and market shifts as they happen, without waiting for the news cycle to catch up.
This kind of pricing pattern is showing up in other markets too.
The Boca Raton mansion that just sold for a record-breaking $75 million with a luxury wellness wing is another example of how ultra-luxury waterfront listings are hitting numbers that would have felt impossible five years ago.
Why This Matters
A $100 million closed sale in Connecticut would not just be a transaction. It would permanently change how the state’s market is perceived nationally.
According to a Realtor.com report, ultra-luxury sales in Greenwich were projected to reach $597 million in 2025 alone, with the H1 2025 median sales price hitting $2.9 million, nearly $1 million above the prior year and the highest first-half median on record going back to 2001.
That is the market this listing is entering.
The Copper Beech Farm sale in 2023 gives us the closest benchmark. Listed at $150 million, it closed at $138.8 million, roughly 8% below ask.
If Cedar Cliff follows a similar pattern, Kathie Lee could walk away with somewhere between $90 million and $95 million. Still a number Connecticut has never seen.
The agent crossover matters too. When Alex Hall made the move from Selling OC to the Hollywood Hills luxury market, it was a reminder that in ultra-luxury real estate, the agent’s market knowledge often matters more than the listing itself.
McElwreath already has the playbook. She wrote it.
You also see this pattern with athletes stepping away and leaving their properties behind.
The story of Aaron Rodgers’ parents selling their California home for $1.68 million while his $3.7 million mansion sits unsold is a different scale, but the same truth: pricing and timing in luxury real estate rarely go exactly to plan.
Kathie Lee has the right agent. The timing is strong. Whether the final number hits $100 million or lands slightly below, this sale will set the conversation for Connecticut real estate for years.
Key Takeaways
- Cedar Cliff at 108 Cedar Cliff Road, Riverside, Greenwich, CT is listed at $100 million
- Kathie Lee and Frank Gifford bought it in 1994 for $7.8 million, a nearly 13x increase over 32 years
- The estate is 13,163 sq ft on a 2.91-acre peninsula with 1,250 feet of water frontage on three sides
- Features include a professional recording studio, 20-seat movie theater, wine cellar, private beach, and boat dock
- Listing agent Leslie McElwreath also represented the $138.8M Copper Beech Farm sale, Connecticut’s all-time record
- It is currently the most expensive home listed in Connecticut. The next closest is $75 million in Stamford.
- 38 Greenwich homes sold above $10M in 2025, up 117% from 2024
- Kathie Lee moved to Nashville in 2019 and held this property for 7 more years before listing
Does Cedar Cliff have a real shot at $100 million, or will it follow the Copper Beech pattern and close below asking? Drop your take in the comments.
Wrapping Up
Cedar Cliff is on the market. The price is historic. The market conditions are the strongest Greenwich has seen in two decades.
Whether it closes at $100 million or lands in the $90 million range like Copper Beech did from its $150 million ask, this sale will be a landmark for Connecticut either way.
Kathie Lee kept this home through grief, through a career change, through a move across the country. She held on for 7 years after leaving. Whatever the final number turns out to be, the house earned the ask.
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Disclaimer: This article is for informational purposes only. All property details and market figures are based on publicly available reports at the time of publication.
