[1] Once a residential neighbourhood thoroughfare flanked by lavishly ornate mansions with Arabesque and European themes of the city's coffee barons and industry entrepreneurs such as the Matarazzo family.

It was based on David Burnham's master plan for Chicago, and attempted to control urban growth of São Paulo.

The plan promoted the decentralization of urban areas, development of automobile routes, and construction low-cost and high-density housing.

The most important of the ones which still stand to this day is Casa das Rosas, near Praça Osvaldo Cruz in the very beginning of the long avenue.

Paulista Avenue underwent a massive renovation and verticalization effort beginning in the 1950s, a trend that followed president Juscelino Kubitschek's vision of rapid economic expansion of Brazil.

The change in economic, social, and cultural status of São Paulo, as exemplified by Paulista Avenue, attracted migration from poorer areas of Brazil and the subsequent appearance of favelas at the perimeter of the city.

Paulista is home to a small native forest park, the Parque Siqueira Campos (English: Siqueira Campos Park), commonly called Trianon, and to the São Paulo Museum of Art (MASP - Museu de Arte de São Paulo).

MASP is known not only for its excellent collection of European and national paintings, sketches, and sculptures by Renoir, Picasso and Modernist Brazilian authors, but also for the modern architecture of its building, whose exhibition room is made of a single block of concrete and glass windows suspended and supported by two vertical concrete columns so the view of 9 de Julho Avenue and the Cantareira mountain range north of here is not spoiled.

The empty space or vault covered by cobblestones is used by the Feira de Antiguidade—Antique fair—every Sunday, open movie projections and other cultural and public events.

The São Paulo Gay Pride Parade in May/June, the largest in the world, and the Saint Silvester Road Race on New Year's Eve take place on this avenue annually.