The Oldsmar name dates to April 12, 1916, when automobile pioneer Ransom E. Olds purchased 37,541 acres (151.92 km2) of land north of Tampa Bay to establish a planned community.

[5] A number of archeological digs in the Oldsmar area revealed small campsites as well as permanent villages that date from the Archaic period (c. 8000 to 1000 BC).

[6][7] In 1916, Ransom E. Olds purchased 37,541 acres (151.92 km2) on the northern tip of Tampa Bay in order to design a planned community.

They also had plots planted with potatoes, turnips, beets, celery, and citrus fruits, among other crops.

Located in the heart of downtown Oldsmar, the building was built in the style of Mediterranean Revival using rare white Italian glazed bricks.

[11] Olds provided financial backing for the Kardell Tractor and Truck Company to move into town.

Renamed Oldsmar Tractor Company, Olds had hoped it would devise a machine to clear out palmetto roots, pine stumps, and other scrub, which all had to be removed by hand otherwise.

[17] Eventually, Oldsmar had dairy and agricultural farms and, in the early days, it was a common sight to see cattle and hogs running loose through the town.

Aside from peppers, tomatoes, corn, gladiolus, and grapes, a banana plantation was established but the winters proved too harsh and the crops failed.

Because Oldsmar sits on a plateau with an elevation never rising over 20 feet (6.1 m) above sea level, it was devastated by the storm.

[19] When he realized Oldsmar was not growing as anticipated, he began liquidating his assets by first selling unplatted parcels of land.

Harry A. Prettyman, a St. Louis promoter, and his associates continued to sell lots in town following Olds's departure.

[25] Major defense contractor and aerospace company Lockheed Martin has a facility in Oldsmar that employed over 600 people as of 2015.