It all started in Savannah, GA, in the early 1900's when the late Larry Dimmitt, Sr. joined the automobile business selling and servicing the Peerless car. Prior to this, Mr. Dimmitt had pursued two other careers in the lumber business and in the railroad business. He was in the "Klondike Gold Rush" before the turn of the century. Before coming to Clearwater, Florida in the early 1920's he had been associated with the Liberty car and the White truck. Mr. Dimmitt was also the Buick distributor in the Georgia area and supplied 16 dealers.

After settling in Clearwater in 1924, Mr. Dimmitt purchased the Ford dealership, then located at the corner of Drew Street and Garden Avenue. He handled Fords and Lincolns until 1933 when he took over sales and servicing of Chevrolets, Cadillacs and LaSalles.

In 1931, the dealership operation was moved to 603 South Fort Harrison Avenue. The Dimmitt Organization grew as Clearwater expanded and in 1952, Larry Dimmitt, Jr. (Second generation dealer) took over from his father. The Chevrolet-Cadillac dual dealership continued to grow and expand and in 1965, a separate dealership facility was provided for Cadillac at 907 Cleveland Street. The Chevrolet Dealership prospered at the original Fort Harrison location. In 1972, Lawrence Dimmitt, III (third generation dealer) took over the Chevrolet dealership from his father, who then continued as the Cadillac dealer on Cleveland Street. In 1975 the Chevrolet and Cadillac dealerships exchanged facilities and Chevrolet remained at its new location at 907 Cleveland Street in Clearwater until the fall of 1985. In October, Dimmitt Chevrolet relocated to its new and current home located on a 14 acre park like setting in Countryside on U.S. Highway 19. In February 1986, the Cadillac dealership relocated to its new 14 acre site bordering south of Dimmitt Chevrolet.