The Picchetti Brothers Winery, also known as the Picchetti Ranch, contains a complex of seven buildings built between 1880 and 1920, which retain their original design details. The Picchetti bothers, Secondo and Vincenso, for whom the ranch was named, were among the first settlers on a ridge which they named "Monte Bello" or "beautiful mountain." They were among the earliest settlers to plant grapes on this ridge which was later to become one of Santa Clara's important vineyard areas. Vincenzo and Secundo Picchetti settled on Montebello ridge in 1877 and purchased an initial 160 acres for $1,500. The ranch went from the original 160 acres to 500 acres by 1904. Vincenzo Picchetti built the first house on the property about 1882, followed by a larger residence in 1886. Both homes, plus the stone winery, were in the Picchetti family until 1976. Instrumental in establishing the Montebello School in 1892, Vincenzo served on the first school board and supplied a room for a teacher at his ranch. Vineyards were the life blood of the town of Cupertino's early economy, although grape parasites destroyed many of the vines in the region in the 1890s. Cupertino remained largely rural until the suburban explosion of the 1960s.
Upon Vencenzo's death in 1904, sons Antone and John ran the winery and ranch. The front porch of the main house was once screened in and acted as an aviary. Later John had numerous aviaries built - one of those aviaries still stands in front of the homestead house. The setting remains intact as part of the Midpeninsula Regional Open Space District. The Santa Clara County Historical Heritage Commission provided funding for the restoration of the winery building. Today the Picchetti ranch and winery on Montebello Road remain as evidence of a thriving viticulture industry in early Cupertino.