527 Holloway St. was likely built near the turn of the century by the Gilbert family and sold to RM Jones, who lived at 521 Holloway, after Mr. Gilbert's death in 1908. Later, JJ Whitley moved into this house from 525 Holloway, next door. Subsequent residents included Herbert Mason, a bookeeper for Thomas and Howard, who lived here around 1920, and M. Donald Bright, a partner in Pritchard and Bright Clothing store at 122 West Main. (Which has a big bright green wall on one side these days)
This house was divided into a duplex at some point - it's impossible to make much out of the front porch in the above picture from 1964, but the change is evident in the picture from the mid 1970s, below.
It appears fairly well maintained, although the original 2-over-2 windows appear to have been replaced with single light windows (with loss of most of the pedimented casings,) and the porch rail replacement is too high with too-skinny balusters. At least they didn't replace the windows with Home Depot specials - the 6 over 6 with the fake plastic muntins (pane dividers).
Looking northeast, 2007