Woods of Bailey Hobson

“Set on expansive, wooded lots within the historic Hobson pocket, the Woods of Bailey Hobson carries the name of the first family to settle DuPage County.”

The Woods of Bailey Hobson sits in central Naperville, in the wooded pocket west of Olesen Drive and north of Hobson Road. It takes its name from Bailey Hobson, recognized as the first permanent settler of DuPage County, who arrived along the West Branch of the DuPage River in 1830 and built one of the region's first grist mills a few years later. That mill once stood at the site now preserved as Pioneer Park, on the neighborhood's southern edge, and Hobson Mill Drive carries the name into the streets today.

The homes here were built largely between the late 1970s and the late 1980s, custom and traditional residences set well back on generous, wooded parcels beneath a mature tree canopy. Colonial and Tudor Revivals sit alongside one-off custom builds, and many of the original homes have been refreshed and expanded over the decades since.

What distinguishes the Woods of Bailey Hobson within the broader pocket is scale, larger homes on expansive lots that give the streets a more open, estate-like feel while keeping the wooded character that defines the Hobson area.

Day to day, the enclave sits against the river corridor. Pioneer Park and the West Branch of the DuPage River trail run along its edge, with Veterans Park a short way down the same trail. Downtown Naperville, the BNSF Metra line, and the I-88 corporate corridor are all a short drive away, a practical balance for buyers weighing an established, private setting against easy access across the western suburbs.