Townsend Winters, a resident of Steuben County, New York, purchased a four-hundred-acre tract of heavily forested land in York County, Pennsylvania, circa 1830, from the heirs of Reverend John Smith for two thousand dollars.

After clearing portions of the land, Winters began work on building a house there and planted an apple orchard.

As other settlers made their way to this area of the county, Winters cleared more of the land, and began sectioning it into individual lots, which he subsequently sold to the new arrivals.

That first community, which would later become known as the Borough of Winterstown, was initially named Apple Grove in recognition of the thriving orchard that Winters had planted.

[6] According to the United States Census Bureau, the borough has a total area of 2.3 square miles (6.0 km2), all of it land.