The Chilson Bailey House · c. 1750 · Middlefield, Connecticut
The hard part's done.
A turnkey home to live in today, a 275-year-old homestead to make your own, and the room — and capacity — to grow into whatever comes next.
A turnkey home to live in today, a 275-year-old homestead to make your own, and the room — and capacity — to grow into whatever comes next.
Built around 1750 and carried on the town's records ever since, the Chilson Bailey House is a genuine piece of Middlefield history — a hand-hewn frame, a walk-in cooking hearth with its original beehive bake oven, wide-plank floors worn smooth by generations.
Most old houses are just old. This one has a name and a lineage — tied to the Bailey family whose roots run deep in Middlefield and neighboring Baileyville. That's provenance no new build can manufacture.
The bones tell the story honestly: exposed chestnut framing, raised-panel walls, a claw-foot tub, and a hearth big enough to stand in. It's a canvas, not a checklist — and because the home sits outside any historic district, you're free to restore it exactly the way you envision, with no review board looking over your shoulder.
Restored on the outside. Ready to be finished within.
Nearly 3,000 square feet of comfortable, modern living was added in 2008–09 — so you settle in from day one and restore the historic wing on your own timeline. Or never. The choice is yours.
A great room under a vaulted ceiling, anchored by a floor-to-peak stone fireplace and lit by an arched Palladian window. A sage-green country kitchen with a butcher-block island. Wide-plank pine floors throughout, a first-floor primary suite, and an enormous open loft above.
Look past the current listing and see what's actually here: a home with the infrastructure and the space to become a true 4–5 bedroom homestead, whenever you're ready.
Bedrooms of septic capacity (1,500-gallon system) — the room to expand is already permitted.
Square feet of historic wing waiting to be finished into bedrooms, studios, or guest quarters.
Level, usable acre — space for a garden, a workshop, an addition, a life.
Finish the wing into two or three more bedrooms and an in-law or guest suite, and you've turned a comfortable home into a compound — on your schedule, at your budget. Here's the canvas:
Not hayloft relics — a solar-topped barn and a detached garage, both usable with power already run, on a level 1.2-acre lot. Workshop, studio, garage for the collection, storage for every project.
A quiet, storied town in the middle of the state — farm stands and ski slopes on one side, a college town and the highway on the other.
The photos tell part of the story. Standing in that hearth tells the rest. Book a private walk-through and I'll walk you through the history, the wing, and everything this property could become.
Book a Private Walk-Through