EXCLUSIVE: Former NFL QB Chris Simms Cuts the Price of His Greenwich Estate Again—Dropping His Ask by Nearly $2 Million

by Kelsi Karruli

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Former Tampa Bay Buccaneers quarterback Chris Simms has lowered the price of his Connecticut estate for a third time—dropping his original $8 million asking price by an additional $700,000.

The 45-year-old—who retired from the NFL in 2010 following a spleen injury—and his wife, Daniella, initially put their longtime Greenwich abode on the market on Feb. 6. Within a matter of months, they had dropped the price by $500,000.

A second price cut in June slashed a further $600,000 from the ask, while a third discount on Aug. 21 saw the athlete's original ask of $8 million lowered to $6.2 million, Realtor.com® can exclusively reveal.

Simms, who now serves as an analyst for NBC Sports, still stands to make a sizable profit on the dwelling he purchased for $2.5 million in 2019—even after he and his wife invested heavily in its restoration and renovation.

The property, which was originally built in 1725, has been updated extensively in the seven years since the couple took ownership.

640 Round Hill Rd, Greenwich, CT 06831
Former Tampa Bay Buccaneers quarterback Chris Simms has once again trimmed the asking price of his Connecticut property—this time by over a half-million dollars, bringing the price down to $6.2 million. (Daniel Milstein Photography)
A fireplace in a living area in Chris Simms equestrian estate in Greenwich Connecticut
The 45-year-old—who retired from the NFL in 2010 following a spleen injury—and his wife, Daniella, initially put their longtime Greenwich abode on the market on Feb. 6 for $8 million. (Daniel Milstein Photography)
A wooden table with chairs in Chris Simms equestrian estate in Greenwich Connecticut
Then, over the next several months, the couple attempted to entice buyers by sprucing up the listing images and reduced the price by over $1 million. (Daniel Milstein Photography)

Today, the property is hailed as a "piece of Greenwich history" with all the luxury of a modern mansion.

"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, which is held by Monica Webster of Douglas Elliman, notes.

The five-bedroom, five-bathroom dwelling features an open floor plan that begins with a living area with a cozy fireplace, windows, and wooden beams on the ceiling.

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

The charming dining area also has wooden beams on the ceiling and a wooden island.

The bedrooms follow the home's minimalistic aesthetic and feature enough space for a queen-sized bed while boasting small windows.

"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.

A fluffy white couch with an Hermes blanket in front of a fireplace in Chris Simms equestrian estate in Greenwich Connecticut
Simms, who now serves as an analyst for NBC Sports, snapped up the dwelling in 2019 for $2.5 million. (Daniel Milstein Photography)
Double sink counter with lights and a large mirror behind it at Chris Simms equestrian estate in Greenwich Connecticut
Originally built in 1725, it has since undergone many restorations and updates. (Daniel Milstein Photography)
640 Round Hill Rd, Greenwich, CT 06831
"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," the listing notes. (Daniel Milstein Photography)
640 Round Hill Rd, Greenwich, CT 06831
According to Robb Report, the couple chose the farmhouse for its impressive parcel, noting to the outlet that they wanted more space for their horses (Daniel Milstein Photography)

"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 states.

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

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

However, they are now moving to a new 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 now share two children.

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