[1] By 1746, a 55-acre tract of the upper Charleston peninsula had been subdivided from a larger parcel and sold to John Drayton who used the land as a farm known as "Pickpocket."
In 1823, Mrs. Sophia Francis Perry Shepherd granted four lots in what she envisioned as “Shepherdboro” to the Episcopal Church.
Legal fights between the family and the city delayed sales but began in 1898 and picked up pace in 1902 when commercial real estate companies were used to market the development.
[1] In 2012, the Preservation Society of Charleston held a special tour of the Wilson's Farm neighborhood.
The build out of the neighborhood bridged an earlier period during which builders followed local customs (resulting in several traditional Charleston single houses) and a modern era during which builders followed national trends (resulting in American foursquares and variants).