Focus on Portrait of Emilia Pia da Montefeltro and analyze the History.
The rear of the work has an inscription saying "Emilia Pia da Montefeltro" and a seal with a fragmentary line, usually interpreted as "[Fo]ntico tedescho di V[enezia]", i.e. the Fondaco dei Tedeschi in  Venice.
The painting was perhaps part of the ducal collection of Urbino, brought to Florence in 1625 as a part of Vittoria della Rovere's dowry. Later it was in Vienna, then in Erlenbach, near Zurich, and was later sold to the Kleinberger Gallery in New York, USA, whence it arrived to the current seat.
The identification with the subject (the wife of Antonio da Montefeltro, described in Baldassarre Castiglione's Book of the Courtier)  is confirmed by a medal attributed to Adriano Fiorentino. However, the attribution to Raphael remains disputed, in a similar way than the Portrait of Elisabetta Gonzaga of the Uffizi. Emilia Pia was in fact a confidant of Elisabetta Gonzaga, and perhaps her portrait was executed to emulate the former's.
Baldassarre Castiglione Florence Zurich Erlenbach Raphael Uffizi Emilia Pia Urbino ducal collection Kleinberger Gallery Vittoria della Rovere New York Antonio da Montefeltro Venice Fondaco dei Tedeschi Vienna Elisabetta Portrait of Elisabetta Gonzaga Book of the Courtier