The F. W. Woolworth Company (Woolworth’s) first came to Middleborough in 1911, establishing a store in the American Building on South Main Street as Middleborough’s first chain department store. Increasing business prompted the company to have a building built to its own specifications on Center Street in 1927-28 (the building most recently occupied by Reedy's Archery), replacing the James Soule House which had originally stood on the site. This new building was built the same year that Woolworth’s principal Middleborough competitor W. T. Grant arrived in town.
The building was purpose built for Woolworth's to that company's specifications by Arthur Shactman of Brookline, the owner of the property in 1927-28. Woolworth's proposed leasing the building for a period of 20 years commencing May 1, 1928 and ending May 1, 1948, with an annual rent of $3,600 for the first 10 years and $3,900 for the remaining years. In return, Woolworth's required the building to be "the same in workmanship and materials as the premises now occupied by the lessee at 297-297A Harvard Street, Brookline, Massachusetts." Specifications for the building were incorporated directly into the lease between Shactman and Woolworth's.
Woolworth's closed its Middleborough store on December 24, 1971.