The son of a cavalry officer, Dimitri Ismailovitch was, from 1900 to 1907, a cadet in Ukraine, from 1907 to 1909 a cadet in St. Petersburg, and in 1911 participated in military maneuvers in France as a young lieutenant. It is interesting that a military career not only did not interfere with Ismailovitch’s passion for painting but rather encouraged it. As he himself recounted, it was in the cadet corps that he met such drawing masters as Lev Dmitriev-Kavkazski’s, whose classes he attended in St. Petersburg, and, while on maneuvers in France, he was able to visit the museums of Paris. All this knowledge and experience (along with his talent) allowed him to leave his military career at the end of the First World War and enter the Ukrainian Academy of Arts in Kiev (one of his teachers was Mykhailo Ivanovych Zhuk), where his first solo exhibition was held. Alas, the whirlwind of revolutionary events forced the artist to leave the Russian Empire. At the end of 1919, Ismailovitch was evacuated to Istanbul. At first things did not go well, and he even had to work at one of the local secondhands. As he himself wrote, he arrived in the city “with a box of paints as the only livelihood.” This box of paints undoubtedly served him well as the city inspired him to paint landscapes almost from the very first minute. Later, works on Byzantine themes (especially after the secretary of the American Embassy, Gardiner Howland Shaw, commissioned from him a copy of one of Kariye Mosque’s mosaics) and still life-paintings were added to the landscapes. It is worth noting that his friend Alexis Gritchenko greatly assisted him in his understanding of Byzantine art. At the same time, Ismailovitch was keen to continue the work of the Russian Archaeological Institute, which was forced first to suspend and then completely wind up its activities. The newspaper article recounting how the artist turned to Halil Ethem Bey with a request to take measures to preserve the Byzantine fresco in the Kemankeş Mosque, and the fact that he wrote a report on the state of the wall paintings in the Kariye Mosque at the request of the Byzantologist Viktor Lazarev, suggest that he did indeed prove himself to be a worthy successor of the Russian Archaeological Institute’s officials. As explained by Gerol’d Vzdornov: “Thanks to Ismailovitch, historians of Byzantine painting have the opportunity to imagine what Kariye’s mosaics and frescoes were like in the interval between their publication in 1906 by Fyodor Schmidt and the beginning of the restoration work of the American Byzantine Institute after the Second World War.” Nadia Podzemskaia examines this matter in detail in one of her articles.
In addition, Dimitri Ismailovitch was one of the leaders of the Union of Russian Painters in Constantinople. He was mainly involved in organising exhibitions and so was in regular communication with local representatives of the art world. He not only took an active part in the Union's collective exhibitions (including First Russian émigré artists in Istanbul exhibition and Exhibition of Russian émigré artists at Taksim Military Barracks where his bust by Roman Bilinski was presented), but also organised at least three solo exhibitions in Istanbul (the first was held at Mayak, Bursa Street 40 – now Sadri Alışık 40, on 20 November 1921; the second on 2 April 1924 in the premises of R.O.S., a Russian club on 15 Telgraf Street, now presumably Tel Sokak 19; the third at the end of October 1924 at Robert College). Here is what the newspapers wrote about his work in the 1920s: “The artist worked a lot and thoughtfully on the views of Constantinople, focusing on the reproduction of the immortal images of Byzantine church architecture with great love. There is a lot of taste in the choice of subjects and in the selection of colours. The old walls and porticoes of the temples on some of the canvases are just excellent, and they deserve more than just a one-day ‘refugee’ exhibition” (Anonymous, “Vystavka Kartin Ismailovitcha”, 1921). His other works, such as still-life paintings with Turkish bath attributes, Turkish crockery and clothing materials speak of a keen interest in local culture and good observation skills. Subsequently, recalling his Istanbul years, he wrote in one of his letters: “It was a very difficult time but an empty stomach never diminished my enthusiasm for painting.”

Approximately seven years in Istanbul turned out to be incredibly fruitful for Dimitri Ismailovitch, but nevertheless in March 1927 he left Turkey and moved to Rio de Janeiro. However, interest in his Istanbul works was so strong that he held an exhibition in Athens at the invitation of the Greek government before moving, and later held exhibitions in Washington and New York (at the request of a local museum). In 1928, after moving to Brazil, another solo exhibition of the artist was held at the Victoria and Albert Museum in London. In subsequent years, while living in Brazil, whose “charm of tropical nature” won him over, he continued to work tirelessly and every year saw the opening of a new exhibition of his works. In Brazil, he mainly improved himself in the portrait genre. According to Rafael Cardoso, "press coverage in Brazil often associated his work with Russian and Byzantine icons, as well as with religious mysticism" (Cardoso 2021, 237). Although it is known that "in the later period he also created non-figurative paintings, which he called 'exercises' and did not show at exhibitions" (Leykind 2019). In 1948, his solo exhibition took place in Bordeaux, France (at that time he was already a citizen of Brazil) where among other works his watercolors of ethnographic nature, depicting Turks, Greeks, Armenians and Arabs of Istanbul were presented. It is also known that he gave painting lessons: from among his students he especially singled out Maria Margarida de Lima Soutello (she worked under the name Maria Margarida), with whom he held several exhibitions. In 1954 he painted icons for the Russian Greek Catholic Church in Sao Paulo. It is also worth noting that he received a huge number and variety of awards and medals for participating in the Brazilian Salon of Fine Arts, and two of his works are permanent exhibits at the National Museum of Fine Arts of Rio de Janeiro (Museu Nacional de Belas Artes).