Roccalbegna is home to several notable fortifications, such as theCassero Senese (built in the 13th century by theAldobrandeschi, renovated in the 15th century) and theRocca Aldobrandesca, located on the hill overlooking the town and theAlbegna river (whence the town's name). Outside the town there is the largecastle of Triana (known from 760), also owned by the Aldobrandeschi and then by theSforza of Santa Fiora; it has maintained its medieval line of walls. The hamlet of Cana has also an Aldobrandeschi-built line of walls from the 13th century.
Also notable is the Romanesque-Gothic church ofSanti Pietro e Paolo (13th-14th centuries, modified in the 18th century). It has a large Gothic portal surmounted by arose window. It houses some parts of a polyptych byAmbrogio Lorenzetti (c. 1340), aPietà byAlessandro Casolani and a 15th-century small fresc ofMadonna with Saints.
