Oakland is a town in Orange County, Florida, United States.

During the Civil War, the Post Office at Oakland was the only one operating within the present-day boundaries of Orange County, as Orlando's was closed from 1861 to 1866.

During a time of great growth in the region during the 1880s, Oakland emerged as the center of commerce in west Orange County.

However, a fire in the business district and a subsequent period of freezes in rapid succession throughout the 1890s, along with the growth of nearby Winter Garden, seemed to ensure that Oakland would remain as little more than a sleepy village.

In 1940, Oakland surpassed nearby Maitland in population, ranking at #6 in the county.

[7] As of the 2020 United States census, there were 3,516 people, 857 households, and 719 families residing in the town.

[12] As of the 2010 United States census, there were 2,538 people, 753 households, and 654 families residing in the town.

14.2% of all households were made up of individuals, and 3.2% had someone living alone who was 65 years of age or older.

Compared to the 2000 Census, Oakland has become more family dominant, with a decrease in both its share of senior citizen population and non-family households.

Oakland has seen an explosion of wealth compared to the American Community Survey numbers last released with the 2000 Census.