168 N. Loudoun Street
Winchester, VA 22601
Open Tuesday-Thursday: 11am-11pm
Open Friday-Saturday: 11am-1:30am
Open Sunday 11am-5pm
1827 House – Northwest corner of Cork and Loudoun Streets
This house was built by Jacob Sperry who originally painted the date on the chimney. Legend tells us that when he completed the house he placed a series of boards across the two chimneys and stood on his head for a dangerously long time. It is a curious story but in researching the property I found something a bit more interesting (don’t I always?).
Around 1743 William Bobbins built on this site a small limestone cottage. Since Cork Street, at the time, was the southern most boundary of first unofficial plan for Winchester, recorded in 1744, this was the first residence lying within the city limits.
In 1748 Mr. Dobbins died and willed the property to his daughter and her husband. The problem is that the property legally belonged to Lord Fairfax and was deeded to James Wood in 1758, ten years after Mr. Dobbins’ demise. The heirs, as well as old Mr. Dobbins were therefore squatters on the property. Curiously nothing seems to have been done about it. Dobbins daughter and her husband died without children and, upon her death the stone cottage stood uninhabited until the first official conveyance of the property to John Conrad in 1817. It was the last lot within the original 1744 plan to be sold yet on it stood the first residence of the city. Furthermore, it was the last property purchased in the town with British Pounds.
Small wonder why Mr. Sperry stood on his head!