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). Originally located at 4 East Sixth Street. Over a period of nearly twenty years, the business slowly outgrew the talents of just one executive. In 1883, John A. Montgomery (1868-1927) was hired to assist Woolley in the services provided by the company. Upon the death of Woolley In 1886, Montgomery consolidated the business with that of Ferdinand L. Gilpin’s (1846-1927) insurance agency, also located in Wilmington. Following this pattern, Montgomery and Gilpin absorbed the insurance agency of Edwin A. Van Trump (1868-1924) in 1904, forming the partnership of Gilpin, Van Trump & Montgomery.

The company incorporated in 1909 and moved its offices to the Du Pont Building. As brokers, they held contracts of major insurance companies such as the Aetna Casualty & Surety Company, Metropolitan Life Insurance Company, and others. In 1918, the company formed J. A. Montgomery, Inc., a separate corporation with offices located in New York City that provided insurance to certain large corporate customers, while Gilpin continued to broker contracts of other insurance companies.

After the death of Montgomery in 1927, the presidency of the company passed to his son, John A. Montgomery Jr. (1898-1932), who tragically died in an airplane accident in 1932. Following these events, ownership passed to a new, younger group in management, which resulted in the election of a Board of Directors that included Robert H. Richards (1873-1951), C. Douglass Buck (1890-1965), and Francis V. du Pont (1894-1962). The board elected Richards as company president and Willard T. White (1898-1970) as executive vice president. In 1941, Gilpin, Van Trump & Montgomery, Inc. was re-activated as an affiliated organization that specialized in real estate sales and mortgages. By 1946, the company was approved to provide FHA loans and, by 1950, became a mortgage loan correspondent for Metropolitan Life Insurance Company; an additional branch facility for insurance and mortgage business was established in Dover, Delaware, in 1966.

In April 1971, a branch office for the Real Estate Sales Department opened in the company-owned Mill Creek Shopping Center at the intersection of Limestone Road and Kirkwood Highway. Gilpin developed both commercial and residential land, and quickly expanded its residential sales operations and intensified its development activities. The company grew to include residential brokerage, mortgage banking and servicing, property management, commercial/industrial sales, office leasing, land development, and corporate relocation services. Accordingly, Gilpin was the only full-service real estate organization in the state of Delaware. In January 1995, Gilpin, Van Trump & Montgomery, Inc. sold its residential real estate sales operation, known as Gilpin Realtors, to Patterson-Schwartz & Associates, Inc. Shortly thereafter, Gilpin formed a partnership known as the Gilpin Mortgage Company, which merged the residential mortgage sales operations of Gilpin and Patterson-Schwartz. The new partnership operated under Gilpin management. Gilpin, Van Trump & Montgomery, Inc. continues operations as a commercial real estate owner and developer in New Castle County, Delaware.