The elder brother of the artist, Freedlander was also raised in New York, attended its public school, and then entered the Massachusetts Institute of Technology, Cambridge, Massachusetts, where he began the study of architecture, receiving his degree in 1889. The following year he continued his study at the Ecole des Beaux-Arts in Paris. In 1895 Freedlander with two colleagues were the first Americans to be awarded formal degrees in architecture from the French institution. He then promptly returned to New York to established his professional practice.
Freedlander enjoyed a highly successful career. He quickly established his reputation by winning a series of architectural design competitions: the Saint Louis (Missouri) Club headquarters, 1897; the National Home for Disabled Volunteer Soldiers, Johnson City, Tennessee, 1904; the Portland (Oregon) Auditorium, 1911; and in 1912 the contest for the design of the Perry Memorial at Put-In-Bay, Ohio, on Lake Erie. In 1928 his submission to the competition for the Museum of the City of New York was successful, and this, his best known work, was completed in 1930.
Freedlander's practice was largely confined to New York and near-by communities. Among his major projects within the city were the Harlem Hospital, 1907; the French Institute, 1929; and the Bronx County Courthouse, 1934. One of his most conspicuous projects, the Fifth Avenue traffic towers, the first of which was erected in 1929, does not survive. Further afield he built the White Plains, New York, municipal building in 1927, and the spa at Saratoga Springs, New York, in 1935.
Freedlander was also active in civic and arts organizations. He was at one time president of the Society of Beaux-Arts Architects, of the Societ‚ des Archtectes Diplomes par le Gouvernement Francais, and of the Fine Arts Federation; and a member of the New York Architectural League, National Sculpture Society, and Municipal Art Society. He was elected a fellow of the American Institute of Architects in 1926.
