19 High Street

Middlefield, CT 06455

Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center chimney Colonial while enjoying the comfort of a beautifully designed 2008 addition. The original 1750 home is not currently livable and is ready for renovation, providing the next owner the chance to restore an authentic piece of Connecticut history at their own pace. Everyday living takes place in the thoughtfully designed 2009 addition featuring 2,963 square feet of living space, a spacious country kitchen with an oversized island, soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, the impressive barn and detached garage provide exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Major improvements-including the addition, detached garage, septic system, 200-amp electrical service, lease solar, and new windows in the original home-have already been completed, allowing you to focus on restoring the historic heart of this remarkable property. Whether you're passionate about historic preservation or simply searching for a property unlike any other, this is your opportunity to restore a landmark while enjoying the comforts of modern living from day one.

Listing courtesy of Debbie Huscher of Real Broker CT, LLC Office Phone: (855) 450-0442 Broker Contact: (860) 918-4580



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Last checked: 2026-08-31 12:01 AM UTC.