This RootsWeb entry says:
John Madison (or Maddison), a ship's carpenter, arrived in Virginia from England in 1653. For paying the passage of twelve immigrants, including himself, he was granted six hundred acres of land through the "headright" system, a system which allowed anyone fifty acres of land for each immigrant whose passage from England he paid. Usually, those immigrants were indentured servants, who worked for a certain number of years in exchange for their passage. Madison's land was on the Mattapony River, at a place called Mantapike, and for the next thirty years, he continued acquiring land through the "headright" system. By 1683, around the time of his death, his estate consisted of nineteen hundred acres on the York and Mattapony Rivers.

After his death, his son John continued enlarging the family estate, becoming a prominent landholder and serving as sheriff and justice of the peace in King and Queen County. In 1714, he and a neighbor, Daniel Coleman, patented two thousand acres of land on the upper Mattapony River. His three sons, John, Henry, and Ambrose, moved to this land, which was forty miles above Mantapike, and began working on their own estates. Of these sons, Ambrose, the grandfather of President James Madison, proved to be the most important Madison in this generation.