What if you woke up every morning to sunlight dancing off the Long Island Sound, with sailboats gliding past your backyard and the scent of saltwater drifting through open French doors? That was daily life for Kathie Lee Gifford at Cedar Cliff, the sprawling estate in Greenwich, Connecticut, that she shared with her late husband, NFL legend Frank Gifford. This wasn’t just a house. It was a 2.91-acre gated waterfront peninsula where Mediterranean elegance met New England coastal charm. And right now, it’s listed for $100,000,000 — one of the most ambitious residential listings the state has ever seen. Let’s take a real walk through Kathie Lee Gifford’s Cedar Cliff estate, room by room, memory by memory.
Kathie Lee Gifford’s Cedar Cliff Estate at a Glance
| Detail | Info |
|---|---|
| Location | 108 Cedar Cliff, Riverside section of Greenwich, Connecticut |
| Community | Indian Head Association — gated peninsula |
| Lot size | 2.91 acres |
| Waterfront | 1,250 feet of direct frontage on Greenwich Cove / Long Island Sound |
| House size | 13,163 square feet across 29 rooms |
| Bedrooms / Bathrooms | 8 bedrooms, 14 bathrooms (9 full, 5 half) |
| Architectural style | Mediterranean villa |
| Built | 1930 by railroad magnate Henry F. Shoemaker |
| Purchased by Giffords | 1994 for $7.8 million |
| Current listing | $100,000,000 (as of 2025) |
| Listing agent | Leslie McElwreath, Sotheby’s International Realty |
| Standout amenities | Private beach, deepwater dock, pool and spa, tennis court, 20-seat private theater, wine cellar, billiards room, 10 fireplaces, greenhouse, recording studio, full-property generator |
The Home’s Gilded Age Roots
Before it was Kathie Lee Gifford’s house, Cedar Cliff belonged to Henry F. Shoemaker, a railroad magnate with a taste for grand European architecture. He built the mansion in 1930, pulling inspiration from Italian and Spanish villas. Think stucco walls, a red-tiled roof, wrought-iron balconies, and arched windows that frame the Sound like living art. The estate became so iconic that the street itself took on the Cedar Cliff name — a rarity that speaks to the property’s stature in Greenwich history. Sotheby’s listing describes it as a “Gilded Age legacy,” and walking through the front door, you understand why.
The terracotta floors, exposed wood beams, and hand-painted tile details carry old-world glamour that has survived nearly a century. In its early decades, the property served as a backdrop for the Cedar Cliff Beach Club, a social gathering point for Greenwich’s waterfront community. What strikes you immediately is the light. It pours in from every angle — especially at the back of the house, where floor-to-ceiling windows blur the line between indoors and out. The towering cedar trees that give the estate its name wrap the property in total seclusion, even though New York City is just a short drive down the coast.
The Heart of the Home — Living and Entertaining Spaces
Cedar Cliff is a 29-room estate, and every room carries weight. The great room stops you in your tracks: a massive stone fireplace anchors one wall, while the opposite side opens onto the Sound through a wall of glass. The house has 10 fireplaces throughout — a detail that speaks to both the era it was built in and the warmth the Giffords brought to every corner.
The formal dining room is draped in crown molding and anchored by a chandelier that catches the sunset, with space for a table that seats twelve comfortably. Downstairs, the entertainment level includes a temperature-controlled wine cellar built to hold hundreds of bottles and a 20-seat private theater that the Giffords added as part of a three-story east wing constructed in the early 2000s. That wing also added a primary suite, an office, and additional living space designed around how the family actually lived.
There is also a billiards room that doubles as a quiet tribute to Frank Gifford’s legendary NFL career — his memorabilia lines the walls, preserved exactly as it was. The kitchen offers marble countertops, custom cabinetry, and a sunny breakfast nook overlooking the gardens. A greenhouse extends the growing season, and a screened porch provides a sheltered spot to watch storms roll across the Sound.
A House That Drew Everyone In
Cedar Cliff was never a quiet estate. It was a gathering place — the kind of house where people arrived and never wanted to leave.
“I used to have Neil Sedaka there all the time. Dolly Parton, Larry Gatlin, you name them. Kenny Loggins, Kevin Costner — everybody’s playing the piano and playing guitar,” Kathie Lee told PEOPLE magazine.
The guest list reads like an awards show seating chart. Regis Philbin and his wife, Joy, were regular dinner companions. Hoda Kotb’s 50th birthday celebration took place on the grounds. Even a young Donald Trump joined the Giffords for tennis matches on the estate’s court. Kathie Lee has described those years simply: “It seemed like we were always celebrating something.”
The Outdoor Oasis That Steals the Show
Inside is impressive. But outside is where Cedar Cliff really shows off.
The centerpiece is the pool and spa area, surrounded by stone patios built for long summer afternoons. Imagine floating on your back, staring up at the sky, with the sound of waves as your playlist. A regulation-size tennis court sits nearby, and beyond that, the grounds open into gardens dotted with mature trees dating back to the Shoemaker era. Hydrangeas, roses, and sea grass blur the edges between manicured landscaping and wild coastal beauty.
But here is the real jaw-dropper: the waterfront. The property sits elevated above the flood zone, with 1,250 feet of direct frontage on Greenwich Cove — a number almost unheard of for private Greenwich estates. A private pier with a deepwater dock stretches into the cove, giving the owner direct boat access to Long Island Sound. There is a private beach tucked below the bluff, and rebuilt sun decks that capture unobstructed views of the water in every direction.
At sunset, the sky turns cotton candy pink and the water shimmers gold. That is not a scene you buy. That is a scene you live.
The recently installed Ludowici terra cotta roof preserves the home’s original Mediterranean character while protecting it for decades to come, and a full-property generator ensures the estate runs without interruption through coastal storms.
The Emotional Goodbye and a New Chapter in Nashville
For Kathie Lee, selling Cedar Cliff was never about the money. It was deeply personal. After Frank passed away on August 9, 2015 — one week before his 85th birthday — the house began to feel different.
“I have my heart and soul, and blood, sweat, and tears in that house. And just memories galore,” she told PEOPLE. “But once Frank passed and my kids went off to start their own careers and start their own families, the music went out of the house for me.”
The couple’s two children — son Cody, 36, and daughter Cassidy, 32 — grew up within these walls. Kathie Lee and Frank raised them surrounded by the sound of waves and the glow of candlelit dinner parties. When both children left to build their own lives, the silence became impossible to ignore.
“Frank and I both came from very humble beginnings, and it was almost unbelievable to us that we would have the opportunity to not only live out our married life there together, but also to raise our children in such a magical environment,” she said.
By 2019, Kathie Lee had relocated to Nashville, Tennessee, where she built a professional recording studio and dove into songwriting and film projects. She has since completed her 37th book, trading the salt air of Greenwich Cove for the creative energy of Music City. The Connecticut estate, no longer her full-time home, was finally ready for a new chapter with someone else.
“We tell everybody that, thank God, we don’t need to sell it, but we’re ready to,” she said.
Why $100 Million Makes Sense in Greenwich
A hundred million dollars is a staggering number. But context matters.
In 2023, Copper Beech Farm — another Greenwich waterfront estate — sold for just under $139 million, setting the record for the highest residential sale in Connecticut history. That sale was handled by Leslie McElwreath of Sotheby’s International Realty, the same agent now representing Cedar Cliff.
“I plan to use the full resources of Sotheby’s International Realty to find the buyer for Cedar Cliff,” McElwreath said. “I also represented the seller of 100 Field Point Circle, the second-highest sale in Greenwich at $50 million. My proven track record, combined with the marketing expertise of Sotheby’s, will prove to be a winning combination.”
McElwreath describes the property’s setting as “extraordinary” — elevated high above the water with commanding panoramic views and direct waterfront access via a private pier and deepwater dock.
The broader Greenwich market supports the ambition. Demand for homes priced above $10 million hit a record in 2025, with 25 sales already recorded by mid-year and projections pointing toward 38 by year’s end. The median sales price in Greenwich climbed to $2.9 million in the first half of 2025 — nearly a million dollars higher than the previous year. Inventory is tightening fast, with fewer than 100 listings remaining. New construction in the luxury segment is moving quickly, too — 214 Clapboard Ridge Road sold for $43.5 million in just 42 days.
“High net-worth buyers do not compromise,” McElwreath said. “They seek exceptional properties in prime locations. Cedar Cliff is a one-of-a-kind opportunity and will attract buyers looking for privacy and resort-like amenities.”
Greenwich continues to pull wealthy buyers for three reasons: proximity to Midtown Manhattan, some of the lowest property taxes among Northeast luxury markets, and a peer community of high-net-worth families. Many are also turning to real estate as a wealth diversification play — and waterfront estates with this kind of frontage and history rarely come to market.
Key Takeaways You Can’t Miss
- Cedar Cliff is a 2.91-acre gated waterfront peninsula with 1,250 feet of direct frontage on Greenwich Cove — not just a mansion, but one of the most significant residential properties in Connecticut.
- The 13,163-square-foot Mediterranean villa was built in 1930 by railroad magnate Henry F. Shoemaker and carries nearly a century of Gilded Age history.
- Kathie Lee and Frank Gifford purchased the estate in 1994 for $7.8 million and spent over three decades transforming it with additions like the three-story east wing, a 20-seat theater, wine cellar, and recording studio.
- The property is currently listed for $100,000,000 with Leslie McElwreath of Sotheby’s International Realty, who previously handled Greenwich’s record-setting $139 million Copper Beech Farm sale.
- Greenwich’s luxury market is surging — record demand for $10 million-plus homes, rising median prices, and tightening inventory create strong conditions for a listing of this scale.
- Kathie Lee’s move to Nashville marked a creative new chapter in music, film, and writing — a transition she describes with gratitude rather than regret.
So, what do you think — could you see yourself watching the sun set over Greenwich Cove from that terrace? If you’re hungry for more celebrity home tours, check out our inside look at Martha Stewart’s Bedford farmhouse next. You won’t believe the garden setup.
