A Former Buccaneers QB Has Been Trying to Sell His Historic Greenwich Estate for 3 Months With No Luck
A house built in 1725 has now had its price cut twice in four months. And it is still sitting.
Chris Simms and his wife Daniella listed their Greenwich farmhouse in February for $8 million. May mein $500K cut liya. Ab another $600K off, bringing the ask down to $6.9 million.
Total reduction: $1.1 million. And the clock is still running.
The House Behind the Number
Simms bought the property at 640 Round Hill Road in 2019 for $2.5 million. He and Daniella had already been Greenwich residents before this, having sold their previous home nearby for $2.7 million.
They moved here specifically for the land. Four acres. Direct access to Greenwich Riding Trails. Three horse stalls. A historic party barn.
A pool house. 3,669 square feet of restored farmhouse with wide-plank antique floors, exposed beams, and multiple fireplaces.
Five bedrooms. Five bathrooms. A chef’s kitchen with white marble. A primary suite with cathedral ceilings, floor-to-ceiling windows, and a private staircase to a library retreat.
The couple described living here as a “true privilege.” Trail rides with horses. Holiday celebrations in the barn. That kind of life.
Now they want out of state, and they want someone who will treasure it the same way.
Four Months. Two Cuts. No Deal.
The listing went live on February 6 at $8 million, held by Monica Webster of Douglas Elliman.
In May, they updated the listing photos, swapping snow-covered lawns for spring greenery and dropped the price by $500,000 to $7.5 million.
That did not move the needle either.
Now the ask is $6.9 million. Down $1.1 million from where it started. For a home Simms bought for $2.5 million six years ago, he is still looking at a significant return if it closes.
But the longer this sits, the more it tells you about where this specific buyer pool actually is.
Why Celebrity Name and Historic Charm Are Not Closing This Deal
This is the part most coverage misses entirely.
Per Q1 2026 Greenwich market data, the $10M-plus segment saw average days on market drop from 278 to 176, still nearly six months of waiting even in a tightening market.
The $6.9M to $8M range, where this property has been sitting, draws an even more deliberate buyer.
Round Hill and Mid Country estates in Greenwich run anywhere from $4 million to $25 million and above, which means this listing is not the only option at this price point. Buyers have choices, and they take their time.
A 300-year-old farmhouse with equestrian land appeals to a very specific kind of buyer, someone who values preservation over gut renovation. That is a narrow profile. Star power does not change the search timeline for that person.
This same dynamic plays out across luxury markets. Even a RHOBH star who spent over $1 million on luxury could not outrun the realities of what the market actually wants at a given moment.
If you want to track stories like this as they break, the WhatsApp channel covers luxury market moves before most outlets catch up.
Why This Matters
The real estate story is just the surface here.
In 2006, during a game against the Carolina Panthers, Simms suffered a ruptured spleen and underwent emergency surgery.
He lost five pints of blood and doctors said another 45 minutes without treatment could have been fatal. He came back, played on, and eventually stepped away from the game.
Then in late April 2026, Simms confirmed he was no longer part of Football Night in America, ending a decade-long run at NBC. Mike Tomlin was brought in as his replacement. Simms said it directly: “That hurt because I do love it.”
So in the same stretch of weeks, he is closing one chapter at NBC and trying to close another chapter at 640 Round Hill Road.
According to Greenwich real estate tracking data, even as the broader market saw a 36% year-over-year increase in median sale price through late 2025, upper-bracket homes remain the segment that takes the longest to find the right buyer.
The data for that is tracked here: Greenwich CT Real Estate Market, Charlie Vinci.
Two price cuts in four months on a property with real historical value says less about the home and more about what buyers at this level demand right now. The right number, the right features, and the right timing all have to line up.
For more on what is happening at the high end, check out this Fortune 500 CEO’s $20 million Bal Harbour condo and Elon Musk’s reported interest in a $300 million Miami Beach megamansion. Same story, different zip codes.
Key Takeaways
- Listed February 6, 2026 at $8 million
- First cut in May 2026 to $7.5 million
- Second cut brings the ask to $6.9 million, a total drop of $1.1 million
- Simms bought the property in 2019 for $2.5 million
- Built in 1725, 5 beds, 5 baths, 3,669 sq ft, 4 acres at 640 Round Hill Road, Greenwich
- Listing held by Monica Webster of Douglas Elliman
- Simms also departed NBC’s Football Night in America in April 2026
- Buyer identity has not been disclosed
What do you think: is $6.9 million a fair number for a 300-year-old home with this kind of land, or is the market just not there for historic estates right now? And should the new owner preserve it exactly as it is, or start fresh? Drop your take in the comments.
Wrapping Up
A home that survived three centuries and one NFL quarterback is still looking for its next owner. The Simms family gave it horses, holiday traditions, and genuine care. That counts for something.
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Disclaimer: This article is for informational purposes only. All details are based on publicly available reports and listing information at the time of publication.
