Former NFL quarterback Chris Simms and his wife, Danielle, have sold their restored 1725 farmhouse at 640 Round Hill Road in Greenwich, Connecticut, for $5.5 million, according to NewsTimes and Coldwell Banker’s property listing. The couple bought the four-acre estate for $2.5 million in April 2019, restored it while preserving its historic character, and initially listed it for $8 million in February 2026 before accepting a lower offer.The sale closes a chapter on one of Greenwich’s more distinctive country properties. It combines a centuries-old farmhouse with equestrian facilities, a heated pool, a restored 18th-century barn, and direct access to protected conservation land and Greenwich’s riding trails.
A home with deep roots
The main house was built in 1725 and offers about 3,669 square feet of living space. Its restoration retained original architectural details, including exposed beams, wide-plank antique floors, and five fireplaces, while adding modern comfort and a more open, light-filled layout.The property includes five bedrooms and five full bathrooms. A newly created primary suite features cathedral ceilings, floor-to-ceiling windows, a dressing room, and a private staircase leading to an office and library retreat.The home also has a gym, a laundry room, a partially finished basement, and a five-car garage. Those features make it more than a historic showpiece, offering the kind of practical space expected in a modern luxury country home.
Why the Simmses bought it
The Simmses purchased the property in 2019 after selling another home in the area for $2.7 million. At the time, they were looking for more space for their horses, and the Round Hill Road estate offered the land, barn, and riding access they needed. The 4.01-acre property includes equestrian facilities with three stalls and a tack room. It also has a pool house, a studio, and a restored 18th-century barn, giving the estate a mix of recreational, practical, and historic appeal, as per the reports.The setting is a major part of its value. The home looks across sweeping meadow views and sits opposite protected conservation land, with direct access to Greenwich’s riding trails.
The restoration approach
The renovation was designed to preserve the farmhouse’s historic identity rather than erase it. The listing describes the result as a blend of historic authenticity and modern luxury, with antique materials and preserved fireplaces alongside contemporary amenities.That balance is often difficult to achieve in an old home. Buyers may want the charm of exposed beams and wide-plank floors, but they also expect reliable heating, cooling, updated bathrooms, and spaces that work for everyday life.The Simmses’ renovation appears to have addressed both sides of that equation. The house retains its farmhouse character, while the new primary suite, office, library, and gym bring it closer to the standards of a modern luxury property.
From $8 million to $5.5 million
The property first hit the market on February 6, 2026, with an asking price of $8 million. That figure represented a 220 percent increase over the couple’s 2019 purchase price, according to Coldwell Banker’s sales history. The price did not hold. It dropped to $7.5 million in May, then to $6.9 million in June, and again to $6.2 million in August.The home went under contract on September 10, about seven months after it was initially listed. It ultimately sold for $5.5 million, which is $3 million more than the Simmses paid for it, though that figure does not account for renovation costs, transaction expenses, or other carrying costs.
What the sale means
The result shows how ambitious pricing can meet resistance even in a high-end market like Greenwich. The property had strong features, including its age, acreage, equestrian facilities, and conservation-adjacent setting, but the market ultimately valued it below the original ask.It also highlights the financial reality of restoring historic homes. A $3 million gain on paper can look very different after accounting for the cost of a major renovation, property taxes, maintenance, and the time involved in preparing a home for sale.Still, the sale represents a successful transition for the property. The Simmses had said they wanted to pass the home to a new owner who would treasure it as much as they had, and the final price suggests there was still strong interest in its combination of history, land, and luxury.
A property with lasting appeal
The farmhouse’s appeal goes beyond its square footage. Its 1725 origins, restored barn, meadow views, and direct trail access give it a sense of place that newer construction often cannot replicate.For buyers seeking a country lifestyle within reach of New York, Greenwich remains a competitive market. The property’s location in Fairfield County, its access to riding trails, and its protected surroundings all add to its long-term appeal.The sale also marks a new phase for Chris Simms, who played in the NFL from 2003 to 2010 and now works as a football analyst for NBC Sports. He and Danielle had planned to move to another state, and the sale of the Greenwich farmhouse gives them the flexibility to begin that next chapter.
