Bernardo di Matteo del Borra Gamberelli given to Bernardo and applied to his brothers, Antonio, Domenico, and Giovanni. Curiously, there is no record of Bernardo's entry into Florence's Guild of Stone and Woodworkers, although matriculation information exists for his brothers.
More than from any single master, Bernardo learned from the experimental atmosphere that suffused Florence in the 1420s. He seems to have been captivated by the "new wave" approaches being put into practice by Brunelleschi, Donatello, Ghiberti, and Masaccio. Perhaps more faithfully than their other followers, Bernardo Rossellino embraced and held true to the classical revival in both sculpture and architecture. Celebrated for his sculpture (the Leonardo Bruni Tomb, Empoli Annunciation group), he achieved particular distinction through his expanding role as an architect, achieving lasting fame for the work done or planned in Rome for Pope Nicholas V and, especially for the rebuilding of the town of Pienza for Pope Pius II. Part of his artistic importance also lay in his entrepreneurial skills which enabled him to assemble a large and highly successful workshop that dominated the stoneworking field in Florence during the 1450s and 1460s.
In 1433, Bernardo is recorded as being in Arezzo, employed by the Fraternita di Santa Maria della Misericordia to complete the facade of the Misericordia's headquarters. His first job presented a considerable challenge. The lower storey of this palace had been completed a half century earlier in the, then, popular Gothic style. Thus the problem confronting Bernardo was similar to that which Alberti encountered a quarter century later when asked to complete the facade of Santa Maria Novella. Bernardo's solution for the unfinished second storey was a three bay design which used a typically Gothic mixed-element frame in the central bay flanked by classical paired pilasters and aediculae, the features of which were taken from the most progressive sources available. Set within the Gothic frame of this second storey is a relief of the Madonna of Mercy, the protectress of Arezzo, spreading her mantle out over the community's citizenry. She is flanked by the kneeling saints Laurentius and Persentinus. Bernardo received his final payment for the project in June 1435, specifically for the two free standing figures of Saints Gregory and Donatus which occupy the aediculae on either side of the Misericordia relief. Rossellino's solution for the Arezzo palace facade fused Gothic and Renaissance elements in a deft, if somewhat awkward, combination aimed at achieving the Renaissance goal of unified harmony. He also clearly displayed, in this initial effort at both sculpture and architecture, a genius for the sort of creative eclecticism that became a major feature of the "Rossellino manner."
Bernardo Rossellino was back in Florence in 1436 to establish his own workshop and to join a crew of stonemasons already at work constructing the Aranci Cloister of the Badia. Payment records, supported by stylistic evidence, indicate that his principal contributions (1436–38) to this project included a handsome stone doorframe and an unusual cross window, both of which are identifiable today. It also is possible that he proposed the addition of the pilaster strips which divide the surfaces of the loggias of the two-storey courtyard into a systematic grid. Documents indicate that Bernardo assumed a more decisive role at the suburban monastery of Santa Maria alle Campora whose cloister (1436) challenges that of Michelozzo at San Marco as the first such structure to have been erected in accordance with a Renaissance aesthetic. In 1444, he received a commission to sculpt two altar figures for the oratory of the Annunciation in the church of St. Stephen in Empoli. In these two representations of the Virgin Annunciate and of the Archangel Gabriel, we find a further development of the artist's decoratively graceful and classical style as well as a recognition of the sculptural styles of Donatello, Ghiberti, and Michelozzo.
Although the stock in trade of the Rossellino shop would have been the supply of building material and simple tasks of stonemasonry, several projects, combining sculptural and architectural features, were of particular significance during the 1440s. One, undertaken in the Palazzo Pubblico of Siena called upon him to design a grand entry way into the Sala del Concistoro. This richly decorated and gracefully classical doorframe is arguably the finest example of the type done in the first half of the fifteenth century and it is certainly one of the most sumptuously elegant of the entire Renaissance. Another project was the triumphal arch wall tomb erected in Florence's church of Santa Croce for the historian and humanist scholar Leonardo Bruni (d.1444), who had served as the State Chancellor of Florence. No documentation survives for the tomb, but two early 16th-century sources credit Bernardo Rossellino for the project and his authorship generally has been accepted. There, however, has been debate concerning the dating of the tomb, with some supporting a date in the late 1440s and others, believing that Bernardo could not have conceived its classical character prior to his stay in Rome, preferring a date after 1455. There is, however, nothing in its design that would preclude the earlier dating. In fact the Bruni Tomb seems a logical continuation of the classicizing manner which Bernardo recently had displayed in his design for the Concistoro door frame in Siena. Accordingly, the Bruni Tomb might best be dated to the years 1446-48. Bernardo Rossellino's Bruni Tomb consisted of a shallow wall niche framed by pilasters and topped by a semi-circular arch. The effect suggests a triumphal arch leading to both the immortal fame desired by the humanist scholar and spiritual deliverance sought by the pious Christian. Bruni's sarcophagus is placed within the niche and it, in turn, supports a brocade-draped bier upon which rests Bernardo's portrait effigy of the statesman. A tondo containing the Madonna and Child flanked by half-length angels appears within the arch above the bier, while two large angelic putti, bearing Bruni's coat-of-arms ascend the archivolt. Bernardo drew upon a variety of sources in arriving at his design for the tomb, including 14th-century wall tombs in Rome done by members of the so-called Cosmati school, as well as the recently executed tomb of Baldassare Coscia (Antipope John XXIII) by Donatello and the Brancacci tomb by Michelozzo. What sets the Bruni tomb apart and established it as the "standard" upon which so many subsequent later Renaissance tombs were based (including that for Carlo Marsupini executed a few years later for Santa Croce by Bernardo's probable pupil, Desiderio da Settignano) was its sense of unity.

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