Fred A. Gregory and John J. Appel formed an insurance and real estate business in 1884, sharing a desk in an office at the corner of Market and Pennsylvania streets. In July 1909, the two men and their sons, Fred Appel and Frank Gregory, formed Gregory and Appel Inc. Within five years, they were working out of a new downtown office space. In addition to selling real estate and insurance, the men were also rental and loan agents. One of their early insurance clients was L. S. Ayres And Company department store in downtown Indianapolis.

John and Fred Appel purchased the interest of Fred Gregory in 1916, making the company a single-family business. In 1928, Fred Appel became president of the company when John Appel died. Gregory and Appel entered real estate development, constructing and selling six houses on North New Jersey Street in 1936. By World War II, the company had built over 250 homes in Indianapolis.

By the 1950s, the company had relocated its office to the building at 120 East Vermont Street. Fred Appel passed the company presidency along to his sons Alan and John C. Appel in 1964. Gregory and Appel continued its success over the next couple of decades, celebrating its centennial anniversary at the Indianapolis Museum of Art (see Newfields) in 1984.

By the 1990s, the company had a 50-person staff and specialized exclusively in insurance. In 1996, the company moved to its newly built headquarters in the Canal District. After a decade in this location, it moved once again, this time into the  historic Capitol View building, built as the home of the HCS Motor Car Company in 1919. Capitol View counted as the 10^th location of Gregory and Appel since its start in 1884.

Throughout the 2000s, the company received multiple awards for service. It was awarded the Indiana Century Award in 2007 by Governor Mitch Daniels. In 2016, the firm earned the Agency of the Year Award from the Independent Insurance Agents of Indiana. The company is family and  employee owned.

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