In the mid 1960s, Rosa Esman established Tanglewood Press Inc., devoted to publishing original limited edition prints and objects. Working with such artists as Christo, Eva Hesse, Jasper Johns, Donald Judd, Roy Lichtenstein, Claes Oldenburg, Robert Motherwell, Robert Rauschenberg and Andy Warhol, Tanglewood Press produced such pioneering portfolios as New York Ten (1965), Seven Objects in a Box (1966), Ten Landscapes by Roy Lichtenstein (1967), Ten from Leo Castelli (1967), Christo's Double Show Window (1972), and Seven Objects '69 (1969). Under the name of Original Editions, the company also published in 1965 11 Pop Artists, which included such famous prints as Roy Lichtenstein's Sweet Dreams Baby, and Andy Warhol's series on paper of Jackie.

Rosa Esman Gallery opened in 1972. After several years, first in the East 80s then on 57th Street, the Gallery moved to SoHo in 1980, where it remained a magnet location until the early 90s. The Gallery represented young emerging artists and also dedicated itself to post World War I avant-garde art. It mounted several exhibitions devoted to works from the Russian Revolution era, as well as important Dada material from a private collection.

In 1994, Rosa Esman founded Ubu Gallery with partners Jack Banning and Adam Boxer, specializing in Surrealist works from the late 20s onward, and in vintage avant-garde photography.

In the year 2000, Rosa Esman left Ubu Gallery in order to work independently and specialize in works on paper and small sculpture from after World War II. Emphasizing Pop and Minimalist works from the 60s and 70s, as well as contemporary art, Esman maintains a continuing interest in the avant-garde movements of the 20s and 30s.

Rosa Esman is a member of the Art Dealers Association of America.