Chris Simms Lists a Restored Antique Farmhouse Estate in Greenwich for $8M

Chris Simms is trading in Greenwich for a new chapter out of state, and with that comes a freshly listed $8 million estate at 640 Round Hill Road that reads like the town’s greatest hits: historic bones, modern polish, and enough land to make the word “acreage” feel like an understatement. The fully restored antique farmhouse spans approximately 3,669 square feet on about 4.01 level acres, with sweeping meadow views and a true country setting directly across from protected conservation land—with immediate access to the Greenwich Riding Trails.

Inside, the house keeps its character front and center—wide-plank antique floors, exposed beams, preserved fireplaces, and original details—while a design-forward renovation brings the comfort up to modern luxury standards. The newly created primary suite is positioned as a standout: cathedral ceilings, a dramatic wall of floor-to-ceiling windows with electric shades, a bespoke dressing room with custom cabinetry, and a private staircase up to a light-filled office that feels like its own retreat.

The layout is built for both everyday living and entertaining, with six bedrooms and five full baths, plus a beautifully finished lower level featuring a substantial recreation room with a fireplace, an additional bedroom, a full bath, and direct exterior access. Outdoors, the property leans into its “host and unwind” potential with a historic party barn and a pool house with a kitchenette—spaces that make holiday weekends and summer nights feel automatic rather than aspirational.

For equestrian buyers (or anyone who just wants that Greenwich lifestyle without needing a second property), the setting is as functional as it is picturesque: three horse stalls with a tack room, plus three paddocks. The Simms put it simply: “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.” Monica Webster of Douglas Elliman holds the listing.

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