Right after the Arts Academy became accessible for women in 1892 she entered it. Her teachers were Pavel Chistyakov, Vasily Mate and Ilya Repin. In 1898 the artist moved to Paris, where she studied under Filippo Colarossi and James Whistler.
 

Experimenting in the field of xylographie, Anna Ostroumova-Lebedeva started using colors and prints from several boards. She considered revival of color xylographie to be her lifework.
 

Anna Ostroumova-Lebedeva joined The World of Art (Mir Iskusstva) group in 1900 and by request of Sergey Dyaghilev made her first Petersburg series of 10 engraving in 1901. She worked in all genres of drawing and painting, including still life, portrait, and genre painting, but most of her prints were on urbanscape, mainly the views of St. Petersburg.
 

Anna Ostroumova-Lebedeva traveled across Europe a lot: she visited Italy (1903, 1906), France (1906), Germany (1911), Holland (1913), Belgium (1913), and Spain (1913). She worked as a book illustrator, contributed for the Zhupel journal (1905), inllustrated the books St. Petersburg (1912) by Vladimir Kurbatov and The Soul of St. Petersburg (1920) by Nikolay Antsiferov. 

After the revolution of 1917 the artist was a member of the expert committee of Narkompros (People's Commissariat for Education). Anna Ostroumova-Lebedeva taught at the Higher Institute of Photography and Photographic Engineering.

In 1924 she joined the Four Arts association. Anna Ostroumova-Lebedeva created the lithograph album St. Petersburg, and the series of wood engravings Pavlovsk. She taught at the Leningrad Institute of Painting, Architecture and Sculpture (from 1934). During the Leningrad blockade she stayed in the city and made several views of it, which are majestic and tragic in their stern simplicity. 
 

Anna Ostroumova-Lebedeva died in Leningrad in 1955.