Chris Simms and his wife, Danielle, turned a 2019 purchase into a high-profile Greenwich, Connecticut, property listing, although the farmhouse ultimately sold after several price reductions.
The former NFL quarterback bought the home at 640 Round Hill Road for $2.5 million in April 2019. Seven years later, the couple listed it for $8 million, more than three times their original purchase price.
Known as the Charles Green House, the farmhouse dates to 1725. Its original structure was expanded in the 1950s and received local historic protection in 2005.
The 3,669-square-foot residence has five bedrooms and five bathrooms, plus wide-plank antique floors, exposed beams and preserved fireplaces. The property also includes a restored 18th-century barn, a pool house and roughly four acres.
The listing highlighted a newly created primary suite with cathedral ceilings and floor-to-ceiling windows, alongside an office and library that broadened the home’s appeal for prospective buyers.
Meadow views, protected conservation land and direct access to Greenwich riding trails give the estate a distinctive setting. Simms and Danielle reportedly wanted more room for their horses when they bought it.
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The $8 million asking price did not hold. The listing dropped to $7.5 million in May 2026, $6.9 million in June and $6.2 million in August.
The property went pending in September and was later reported sold. The final sale price has not been disclosed, leaving the couple’s eventual return on the investment unknown.
Simms played in the NFL from 2003 to 2010, spending time with the Tampa Bay Buccaneers, Denver Broncos and Tennessee Titans. He later moved into broadcasting and became an NFL analyst for NBC Sports.
The sale closes the Greenwich chapter for the Simms family, ending the run of a historic property that combined colonial character with extensive grounds.
