Chalfin entered Harvard College in 1894 but left after two years to become an artist, enrolling at the Art Students League of New York to study painting.

After graduating in 1898, he was accepted at the École des Beaux-Arts in Paris, where he studied painting with Jean-Léon Gérôme, a historic genre painter who had previously taught Thomas Eakins.

In 1910, Chalfin began his most notable and successful project collaborating with F. Burrall Hoffman on the landmark Villa Vizcaya for the industrial magnate James Deering.

Deering was an heir of the International Harvester fortune and had acquired substantial land on Biscayne Bay in present-day Miami, Florida.

[4] Little is documented of Chalfin's later career; he produced several drawings for unrealized houses on Miami Beach[5] and decorated the apartment of actress Lillian Gish, friend of James Deering.