Believed to have been erected in the 1860s for the Hon. Charles Connell, this Gothic Revival house was leased to Charles Bailey. C. Bailey worked as a shoemaker and carpenter from the 1870s until his death in 1902, and he is suspected to have been involved with the Bailey Brothers Boot and Shoe Store, which operated on Main Street prior to its destruction in the Great Woodstock Fire of 1877.

In December 1975, a fire ravaged the home’s interior. Thankfully, the exterior, with its intricate Gothic Revival bargeboards and finials, was unharmed. By the end of 1976, the interior was completely reconstructed.