EXCLUSIVE: Former Tampa Bay Buccaneers QB Chris Simms Slashes Another $600K From Price of 300-Year-Old Greenwich Estate

June 17, 2026 - 01:45

Former Tampa Bay Buccaneers quarterback Chris Simms has reduced the asking price on his 300-year-old Greenwich estate by another $600,000. This marks the second price cut since the property first hit the market four months ago.

The historic home, which blends colonial charm with modern updates, originally listed for a figure well above its current price point. Simms, who played in the NFL for seven seasons and later became a football analyst, has been trying to sell the estate since late last year. The latest reduction brings the total drop to over a million dollars since the initial listing.

Real estate records show the property sits on several acres in one of Connecticut's most sought-after towns. The house itself dates back to the early 1700s, offering a rare combination of antique character and contemporary renovations. Features include wide-plank floors, exposed beams, a gourmet kitchen, and multiple fireplaces.

Local agents say the market for high-end historic homes in Greenwich has softened recently, with many sellers adjusting expectations. Simms' repeated price cuts suggest he is eager to close a deal. The property is now listed at a price that some consider more realistic for its age and condition, though it remains a significant investment.

Simms purchased the estate several years ago and invested heavily in upgrades. Whether the latest reduction will attract a buyer remains to be seen, but the home remains one of the more notable properties currently available in the area.