[1] The Caleb Wiley House is set on the north side of North Street, a major east–west route through residential areas of northwestern Stoneham, amid 20th-century residential houses that are mostly on smaller lots.

It is a 2+1⁄2-story wood-frame house, five bays wide, with a side-gable roof, twin rear-wall chimneys, clapboard siding, and a granite foundation.

Its front door is sheltered by a portico that is early 20th century in appearance, and has flanking sidelight windows.

The house was built about 1826 by Caleb Wiley, at a time when North Street was lined with larger properties mainly in agricultural use.

The original 47-acre (19 ha) lot of this house has long since been subdivided into residences, but this property retains mature plantings, and the main house is relatively little-altered since its construction.