Closely comparable, particularly in the delicate and feathery handling of foliage and the strongly hatched shadows of the architecture, to Giorgione's View of the Castel San Zeno, Montagnana, with a seated figure in the foreground now in the Boymans-van Beuningen Museum, Rotterdam (G. Luitjen and A.W.F.M. Meij, From Pisanello to Cézanne, exhib. cat., New York, Pierpont Morgan Library, and elsewhere, 1990-1991, no. 56). The Rotterdam drawing is the only other one given to Giorgione. Its attribution dates back to Padre Sebastiano Resta, who owned it in the late 17th Century.
Both drawings illustrate Giorgione's interest in the famous sfumato effects of his contemporary Leonardo da Vinci, as noted by Giorgio Vasari in his otherwise rather biased account of the artist in his Life of Titian. The present drawing is in notably fresher condition than the Rotterdam sheet, which was the subject of an unfortunate attempt by Padre Resta at amateur restoration. In his notes on his collection, transcribed by the Richardsons in the Lansdowne manuscript at the British Museum, Resta declares 'e mi son ingegnato di lavarlo con aqua calda meglio che ho saputo' (A.E. Popham, 'Sebastiano Resta and his collections', Old Master Drawings, June 1936, p. 19).
The Tietzes noted that the city in the present drawing may be Castelfranco, and suggest that it may be a study from nature. The Rotterdam drawing, which was also traditionally identified as a view of Giorgione's native Castelfranco, is a view of the walls of the Castel San Zeno on the road between Montagnana, near Este, and Vicenza.
The present drawing was executed from nature by Giorgione, probably to be used in the background of one of his paintings, even though it does not feature in any of his surviving compositions. The view appears nonetheless in the background of two near contemporary Venetian pictures. It can be found, with minor differences, in the background of a painting of Saint Sebastian by a follower of Giovanni Bellini, perhaps close to Francesco Vecellio, formerly in the Thyssen Collection (F. Heinemann, Giovanni Bellini e i Belliniani, Venice, 1962, no. V445, fig. 871; Sotheby's, London, 27 November 1963, lot 112). It also appears, again slightly altered, in a painting of the Madonna and Child by Andrea Previtali datable circa 1504 formerly in a Berlin private collection (J. Meyer zur Capellen, Andrea Previtali, Doctoral Thesis, Würzburg, 1972, no. 8). Although uncommon, a number of pictures painted around 1500 show Venetic towns in the backgrounds of biblical subjects, for example Marescalco's Madonna with Saints John the Baptist and Catherine in the collection of the Cassa di Risparmio, Padua, which like the Rotterdam drawing shows the walls of Montagnana (R. Pallucchini, 'Una nuova opera del Marescalco', Arte Veneta, 1972, pp. 31-38).