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

11 hours ago 1

Former Tampa Bay Buccaneers quarterback Chris Simms has slashed another $600,000 from the price of his 300-year-old Greenwich, CT, estate—marking the second time he has lowered his ask since listing the property just over four months ago.

The 45-year-old—who retired from the NFL in 2010 following a spleen injury—and his wife, Daniella, put their longtime Greenwich abode on the market on Feb. 6 for $8 million, property records show.

At the time, the couple showed off a slew of images of the retreat covered in snow. However, in May, they decided to spruce up the listing by adding a fresh new set of photos that showed off the property in the spring—while also offering up an enticing $500,000 price cut.

Now, Simms and his wife are looking to further appeal to a buyer by bringing their asking price down to $6.9 million.

Simms, who works as an analyst for NBC Sports, snapped up the dwelling in 2019 for $2.5 million—just over a third of the price it is now listed for.

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Former Tampa Bay Buccaneers quarterback Chris Simms has slashed another $600,000 from the price of his 300-year-old Greenwich estate.Mike Coppola/Getty Images for Bleacher Ball

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It marks the second time he has lowered his ask since listing the property just over four months ago. Daniel Milstein Photography

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The 45-year-old—who retired from the NFL in 2010 following a spleen injury—and his wife, Daniella, put their longtime Greenwich abode on the market on Feb. 6 for $8 million, property records show.Daniel Milstein Photography

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Now, Simms and his wife are looking to further entice a buyer by bringing their asking price down to $6.9 million. Daniel Milstein Photography

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Simms, who works as an analyst for NBC Sports, snapped up the dwelling in 2019 for $2.5 million—just over a third of the price it is now listed for.Daniel Milstein Photography

But the property's illustrious history dates far beyond the Simms family's ownership. Built in 1725, it has since undergone many restorations and updates.

Still, the listing, which is held by Monica Webster of Douglas Elliman, highlights the home's impressive lineage, describing it as a "piece of Greenwich history" that sits on a very picturesque piece of land.

"A fully restored antique farmhouse offering approximately 3,669 square feet of refined living space, set on extraordinary level acreage with sweeping meadow views and an irreplaceable country setting across from protected conservation land with direct access to the Greenwich Riding Trails," the listing notes.

Upon entering the five-bedroom, five-bathroom dwelling, guests are greeted with an open floor plan that begins with a living area with a cozy fireplace, several windows, and wooden beams on the ceiling.

The chef's kitchen boasts state-of-the-art appliances, a white marble island, and white cabinetry.

Adjacent to the kitchen is a charming dining area with wooden beams on the ceiling and a wooden island.

The bedrooms follow the same minimalistic aesthetic as the rest of the home and feature enough room for a queen-sized bed while boasting small windows.

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But the property's illustrious history dates far beyond the Simms family's ownership. Built in 1725, it has since undergone many restorations and updates.Daniel Milstein Photography

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The listing, which is held by Monica Webster of Douglas Elliman, highlights the home's impressive lineage, describing it as a "piece of Greenwich history" that sits on a very picturesque piece of land.Daniel Milstein Photography

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The primary residence is described as "a fully restored antique farmhouse offering approximately 3,669 square feet of refined living space."Daniel Milstein Photography

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The dwelling features plenty of fitness-focused amenities, including a gym, spa center with a massage chair, and an outdoor entertaining area with a foosball table.Daniel Milstein Photography

"The residence blends historic authenticity with modern luxury, featuring wide-plank antique floors, exposed beams, preserved fireplaces, and original architectural details," the listing notes.

The bathrooms feature double vanities, a large glass-enclosed shower, a marble soaking tub, and sliding barn doors.

Elsewhere, there is a gym, spa center with a massage chair, and an outdoor entertaining area with a foosball table.

Throughout the home, modern aesthetics have been meticulously merged with historic charm, carefully preserving the property's original elegance, while also breathing new life into its antique bones.

"A thoughtful renovation delivers elevated comfort throughout, including a newly created primary suite with cathedral ceilings, floor-to-ceiling windows, a bespoke dressing room, and a private staircase to a serene, light-filled office and library retreat for everyday living," the listing goes on.

According to Robb Report, Simms and his wife have lived in Greenwich for many years, having previously sold another dwelling in the area for $2.7 million before relocating to their farmhouse.

They chose the farmhouse because of its impressive parcel, noting to the outlet that they wanted more space for their horses.

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Throughout the home, modern aesthetics have been meticulously merged with historic charm, carefully preserving the property's original elegance, while also breathing new life into its antique bones.Daniel Milstein Photography

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Before settling down in Connecticut, Simms enjoyed a lengthy career in the NFL, a career that began at the University of Texas at Austin, after which he was drafted by the Buccaneers as the last pick of the final round in the 2003 NFL draft.Daniel Milstein Photography

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Simms remained with Tampa Bay until 2008, when he was released by the team. He was later picked up by the Tennessee Titans, with whom he played for a year before moving to the Denver Broncos.Daniel Milstein Photography

However, they are now seeking a move to another state and want to pass their current dwelling to a new owner who will treasure it as much as they have.

“Being the steward of this remarkable home and property has been a true privilege. Our family has shared so many unforgettable moments here, from leisurely trail rides with our horses throughout the neighborhood to enchanting holiday celebrations in the historic barn," the couple told the outlet.

Before settling down in Connecticut, Simms enjoyed a lengthy career in the NFL, a career that began at the University of Texas at Austin, after which he was drafted by the Buccaneers as the last pick of the final round in the 2003 NFL draft.

Simms remained with Tampa Bay until 2008, when he was released by the team. He was later picked up by the Tennessee Titans, with whom he played for a year before moving to the Denver Broncos.

After a brief return to the Titans, the quarterback's career came to an end, with many pointing to a 2006 spleen injury as the reason for his retirement from the NFL.

He briefly tried his hand at coaching, signing with the New England Patriots in 2012 as an offensive coach, as well as a scouting expert, but he made a move into broadcasting after just a few months.

Simms and his wife, who met in high school, tied the knot in 2004 and share two children.

Kelsi Karruli is a senior celebrity reporter who joined Realtor.com in 2025. She writes about trends encompassing real estate and celebrity properties. She previously wrote for Daily Mail, True Urban Culture, and JMedia Corporation, where she specialized in covering celebrities, relationships, psychology, and gender issues. She has a bachelor's degree in journalism from Pace University, where she received the James Rose Award for excellence in journalism. When she isn’t updating readers on A-listers' moves, she is spending time with her cat, Mary, and cheering on the Albanian soccer team.

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