This small populated, heavily wooded hamlet in northwest Southampton Town was virtually uninhabited by whites in colonial times. Among its early settlers were Dutch who settled in the area about the end of the 18th Century. They gave the location its name because it reminded them of Flanders, a region of Holland. In the 1800s, families from New York City and the 5 boroughs spent their summer months in Flanders. The community also produced cordwood, and loggers used it as a rest stop on their way to woodlots on the South Fork.
Before World War II, the few residents were mostly blue-collar people who had more in common with adjoining Riverhead than with most of their resort town. During the 1950s and 1960s, small suburban ranch-style homes on small lots popped up along Flanders Road. Many were summer places, but most are now year-round. In the past 20 years, Flanders has seen the influx of many new, costlier homes, especially along Pleasure Drive in the thick pine barrens between Route 24 and Sunrise Highway.