The City of DeLand is a town with a rich history and a close community, bound together by its unique heritage. Henry A. DeLand founded DeLand in 1876, with the purchase of a $1,000 plot of land. He decided to move to the area after visiting his brother-in-law, O.P. Terry, who was living in an area called Persimmon Hollow. Mr. DeLand was a prosperous businessman in New York, but chose to move to Persimmon Hollow.

Mr. DeLand's plan was to develop the area by convincing settlers to come to DeLand and buy land from him. If they didn't like the area they could sell the land back to Mr. DeLand within the first two years of settlement. He became a generous benefactor to the settlers, enabling them to build schools and churches. The settlement was located near what is now Woodland Boulevard and New York Avenue. One winter there was such a bad freeze that the settlers of DeLand lost their crops. These people could no longer stay in DeLand, so Mr. DeLand bought all land back from them.

The following year, the Volusia County Court house was moved from Enterprise to DeLand, a big step for such a small area. The courthouse was rebuilt in the same spot in 1927 and is considered to be one of the most beautiful in the state of Florida.

A major development and contributor to the furthering of prosperity for the DeLand area was the construction of roads. In 1916, Woodland Blvd was bricked in one direction to Old Daytona Road and in the other direction to Orange City. New York Avenue was also bricked down to the St. Johns River. The following year, a road was built to connect DeLand, Daytona and New Smyrna. In 1960, International Speedway was rebuilt with four lanes going to Daytona.

In the 1920's, DeLand left the same prosperity as much of the rest of the country. DeLand had its first tremendous growth spurt, both in population and building. A new style of Mediterranean architecture was seen. Subdivisions were opened all over the area and sidewalks were installed downtown. The city limits were expanded west to the river, east to lake Winnemissett, and south to Orange Camp Road and north to Daytona Road. The expansion of the city lasted but a few years. In 1928, the great depression brought hard times to the city. Subsequently, it was reduced to one square mile. DeLand recovered the economic hardships and has continued to prosper even today.