Enterprise is an unincorporated community in Volusia County, in the U.S. state of Florida, and its former county seat. Situated on the northern shore of Lake Monroe, it is flanked by the cities of DeBary and Deltona. Enterprise was once the head of navigation on the St. Johns River and at various times, the county seat for three different counties: Mosquito, which was renamed as Orange; and lastly, for Volusia, which was formed from part of Orange County.

In 2006, Volusia County government approved a historic overlay which designates Enterprise as an "area of special concern" as a historic village. This establishes a defined historic district within the community and ensures that any development must follow strict guidelines.

In 1565, Pedro Menéndez de Avilés explored the St. Johns River, perhaps reaching Lake Monroe. At the time of contact with Europeans, the area was home to the Mayaca Indians, who lived in small villages. They collected snails and shellfish, hunted turtles, deer and alligators, and gathered roots, nuts and berries for food. The Enterprise midden or shell mound accumulated over thousands of years from the debris of cooking and toolmaking by the ancestors of the Mayaca. Beginning in the First Spanish Period, Florida Indians fell victim to European diseases, forced labor, missionization, and slave raids from the English militia of the Carolinas allied with invading tribes from the north. By the 1760s, Florida's native cultures, including the Mayaca, Timucua, Apalachee, Ais, Surruque, Calusa, and Tequesta, had been decimated. Later called Seminoles, Indians from Alabama and Georgia moved in to fill the void left by native Florida tribes.

Following the acquisition of Florida by the United States in 1821, the Seminole had conflicts with encroaching settlers and troops throughout the Seminole Wars, when the United States tried to remove the Seminole to Indian Territory. In 1835, the Seminole burned Palatka, a major port on the St. Johns River, then the major artery into Central Florida. Consequently, the US built Fort Kingsbury, a stockade defense, in 1838 at Enterprise in the area of what is now Thornby Park, across the lake from Fort Mellon, built in 1836 at Mellonville (now Sanford).

To displace the Seminole, in 1842 Congress passed the Armed Occupation Act, granting 160 acres (0.65 km²) to settlers who would clear, cultivate and hold 5 acres (20,000 m²) for five years. Over 200,000 acres (800 km²) south of Palatka were opened for development. One of more than 1,000 who applied was Cornelius Taylor from San Pablo (now Mayport), a former timber agent and first cousin to General Zachary Taylor. In 1841, he and about 20 others founded "Enterprise" at Fort Kingsbury, which had been abandoned after six weeks, and filed for homestead the next year.

Taylor built an inn atop the shell midden to attract visitors traveling by shallow-draft steamboat from Palatka, the furthest upstream that ocean-going vessels could navigate. Orange groves were planted, and a gristmill established, together with a sawmill to cut southern live oak, prized by the U.S. Navy for warships. In 1843, Enterprise became county seat of "Mosquito County". The latter was renamed as "Orange County" in 1845, and the county seat was moved to Mellonville. An epidemic believed to be smallpox claimed Taylor's oldest daughter and nine of his slaves in 1842, and he left in 1847.

In 1851, Jacob Brock bought land a mile west of the original settlement, where he built a wharf and laid out streets and lots. A steamboat captain with "a notable reputation for the lavish and original nature of his profanity", he had transported to Enterprise many invalids seeking the climate and sulfur springs, which were believed to be curative for a variety of ailments. In 1854, he completed The Brock House, a 2+1⁄2-story hotel with accommodations for more than 50. That year Volusia County was organized from territory of Orange County, and Enterprise was designated as its county seat. Brock operated the first regular steamboat passenger service from Jacksonville to Palatka, expanding to Enterprise.

It was a 206-mile (332 km) trip aboard the Darlington, which departed Jacksonville at 8:00 AM on Saturday, timed to receive passengers discharged from ocean-going ships. It would arrive and spend Sunday in Palatka, from which it departed at 5:00 AM on Monday morning, docking at Enterprise that evening. Only by daylight did prudent captains navigate the narrow, crooked upper part of the St. Johns River. Crew members had to watch for snakes, slithering aboard out of Spanish moss in overhanging trees, and also for alligators, which the crew shot before the reptiles could tangle with the paddlewheel. Soon, an additional danger would imperil the waterway—the Civil War.