The gate "Porta San Matteo" is located on the second walls circle of the town that was build during the 12th. Century; the walls originally present seven entrances to the town.

The gate is surmounted by a double arch, ogive and depressed, and is surrounded by six small arches that were build successively. This gate overlooks the first town suburbs, the road to Certaldo and the small tower "torrione dei frati".