He studied painting (1946-1947) at the Athens School of Fine Arts with Dimitrios Biskinis, Epameinondas Thomopoulos and Umbertos Argyros, and sculpture (1947-1954) with Michalis Tombros. He continued at the Academies of Fine Arts in Florence (1954-1957) and Rome (1958-1961), with Pericle Fazzini and Venanzo Crocetti respectively. In Italy, he associated with prominent artists, such as Giacomo Manzu, Marino Marini, Giorgio de Chirico, Giorgio Morandi and Henry Moore. He travelled to European cities to study in museums. In 1958, he established the first bronze casting workshop at the Athens School of Fine Arts and from 1969 to 1985 was professor at the department of sculpture, at which time he introduced the systematic teaching of theoretical texts.

His work has been presented in solo exhibitions, and a retrospective exhibition was held at the National Gallery in Athens in 1995. He also participated in group exhibitions, including Panhellenic exhibitions, the 1961 Alexandria Biennale, in which he won the gold medal, and the 1979 Sao Paulo Biennale.

A great admirer of Renaissance art with the human figure always as his starting point, Dimitris Kalamaras in his early work remained faithful to the visible reality. Expressionistic elements emerged in his compositions in 1954-1965, and later on his work became more structural, built in geometric volumes – the outcome of extensive study and meticulous measurements, consistent with his faith in order, harmony, symmetry, and in everything that is based on the number principle.