The oldest written mention of the Oostendorper watermolen (Oostendorp watermill) - a corn and oil mill on the Buurserbeek - is found in a deed from 1487. The mill was then located about 1 km downstream. In 1547-1548, the double mill was rebuilt at its current location. It also received its current name then, which comes from Johan ten Oostendorp who was the miller in 1547.

During the Eighty Years' War (1566 - 1648), the water mill was destroyed. In 1633, Willem Ripperda tot Weldam received permission to build the Oostendorper mill on the current site. Two years later, the mills were back in operation. During the next two centuries, they passed from one owner to another several times, by inheritance or by sale.

In 1946, a flood of water washed away the oil mill; it had been rebuilt four years later. In the late 1980s, the Oostendorper watermolen was thoroughly restored and made millable again. Volunteer millers regularly grind grain and crush oil. The municipality of Haaksbergen owns the mill. It is the oldest double water mill in the Netherlands.