Gilpin, Van Trump & Montgomery, Inc. provided insurance sales and service to property owners. The business was established in 1865 in Wilmington, Delaware, by businessman James Woolley (1818-1886). By the early-to-mid twentieth century, the company specialized in real estate sales and service, as well as mortgages, becoming Delaware's only full-service real estate organization. The records include minutes, corporate histories, publicity material, as well as information on company properties, and documents the company's rise from a small insurance company to a large, multi-service insurance, real estate, mortgage, and investment firm.