The original wood structure that stood here (built sometime after 1900) burned in May 1928. It was at the time occupied by H.S. Pendergraft Motor Company (first a Dodge dealership and then a Chevrolet dealership) and service station.
Sometime between 1928 and 1933, a small brick building was built on the site; it housed Squires Grocery Store and Burroughs Auto Service.
By 1930, the MacMillan Motor Company (Chevrolet) was utilizing the property, and fully moved to the property in October 1934. In 1935 MacMillan sold the business to Nolan-Simmons Chevrolet which then became Nolan-Tufts Chevrolet (or vice versa?); part of the structure also housed the Myrick Cash Store.
In late 1941, Jack Hazzard obtained the property and building to house his automobile dealership business, the Hazzard Motor Company. The structure was greatly remodeled and expanded in 1948 by/for Jack Hazzard for his business.
View south west, still under construction, 1948 (screenshot from the film "This is Chapel Hill")
The showroom and salesroom were in the front of the structure, on Franklin Street, with the service bays and garage entrances along Roberson Street.
In 1956, Hazzard sold the company, and it became Harriss-Conners Chevrolet.
April 21, 1958 (photo by Bill Prouty/CHW)
1962 ad (note change to modern style phone number)
In 1963 Orville B. Campbell purchased the building to produce the Chapel Hill Weekly newspaper, and apparently nicknamed it the Bentley Building (after his mother's maiden name).
Campbell moved the Chapel Hill Weekly a few doors down Franklin Street circa 1973. By 1975, the structure's rear housed a variety of businesses and the front was used by the Chapel Hill Telephone Company (operated by UNC), and from 1977 to 1981 it was the local offices for the Southern Bell Telephone Company.
After Southern Bell
moved across Franklin Street, Bear Mayhew Realty
and Swozy's Computer Service
occupied the structure for a few years. From 1986 to 1988 Algonquin Books
occupied the building, followed by House Hunters, Inc
. and then Coldwell Banker/Realty
. Circa 1991 the Chapel Hill Board of Realtors
moved into the building.
There's been some window shenanigans (with faux shutters and all) with the last renovation of the structure, but otherwise the exterior of the struture has kept many if not most of its historic/fauxlonial architectural details.
View south west, June 2019 (via Google Streetview)