Silivri, the ancient Greek Selymbria or Selybria (Greek: Σηλυ(μ)βρία), owed its historical importance to the natural harbor and the position on the major commercial roads. It was a colony of Megara founded on a steep 56 m high hill east of the bay, but excavations show that it was a Thracian settlement before it was a Greek colony.
According to Strabo, the city's name is a combination of the name of the mythological founder of the city, Selus, and the Thracian word that Strabo thought was used for polis, "bria". This, however, did not mean polis, and had another meaning.
Silivri is the birthplace of the physician Herodicus, and was an ally of the Athenians in 351 BC. Until the second half of the 2nd century BC, the city could preserve its autonomy, but after its neighbours Byzantium and Perinthos became more powerful, the city fell under their control during the next centuries. The settlement shrank into a village under the governance of the Roman Empire. In the early 5th century, the town was officially renamed Eudoxiopolis (Εὐδοξιόπολις) in Greek, during the reign of the Byzantine emperor Arcadius (377–408), after his wife Aelia Eudoxia, though this name did not survive. In 805 AD, the Bulgarian Khan Kroum pillaged the town. In the late 9th century, Emperor Michael III constructed a fortress on the top of the hill, the ruins of which still remain, during an era in which the Byzantine Empire suffered attacks by Saracen corsairs and Russians. With the Fourth Crusade, and the fall of Constantinople to the Latin Empire in 1204, the fortress fell in quick succession to the Latin Empire, Bulgarian, back to the Latins and finally was recaptured by the Byzantine successor state of the Empire of Nicaea in 1247, who were finally able to recapture Constantinople and restore the empire in 1261.
In 1346, the Ottomans became an ally of the pretender for the Emperor John VI Cantacuzenus (1292–1383), and helped him against his rival John V Palaeologus (1332–1391). The same year, Sultan Orhan I married Theodora, the daughter of John VI in Selymbria.
In 1399, Selymbria fell to the Ottomans, marking their complete encirclement of Constantinople by land in Europe. Many contemporary observers believed from then on it was a mere matter of time before the Ottomans took the Byzantine capital. However, after their disastrous defeat at the hands of Timur the Ottomans returned Selymbria and several other possessions to the Byzantines in 1403. It was sometimes attacked by the Ottomans in later years, but was not captured.
During the Fall of Constantinople in 1453, Silivri, along with Epibatos, stood up against the Ottoman armies, and surrendered only after the city had fallen. Selymbria extended out of the walls only during the Ottoman era because the non-Muslim residents like Greeks, Armenians and Jews lived within the city walls, and the Turks built their houses outside the walls at the coast. While the non-Muslims were engaged mostly in growing grapes, vinification and silk production, the Turks earned their life by fishing and making yogurt. The town remained a summer resort during the Ottoman time, as it was during the Byzantine era.
On the order of Suleiman the Magnificent, architect Mimar Sinan built 1562 a stone bridge with 33 arches just west of Silivri. The historical bridge, called "Uzunköprü" (The "Long Bridge"), is still in use today, however one arch is not visible due to sedimentation.
Prior to World War I, some Silivrian Jews immigrated to the town of Camagüey, Cuba. Russians occupied Silivri on February 5, 1878 for 1 month until 3 March 1878. Bulgarians occupied it on November 16, 1912 for 9 months until May 30, 1913.
According to the Ottoman population statistics of 1914, the kaza of Silivri had a total population of 16.470, consisting of 10.302 Greeks, 3.759 Muslims, 1.427 Jews, 781 Armenians, 103 Bulgarians and 98 Roma people.Kemal Karpat (1985), Ottoman Population, 1830-1914, Demographic and Social Characteristics, The University of Wisconsin Press, p. 184-185
During the war, many more Sephardim in the city left as conditions worsened due to the war. Many of these Turkish Jews emigrated to the United States settling primarily in New York and Seattle. Others went to Palestine, France and South America.
According to the Treaty of Sèvres, Silivri became a part of Greece on July 20, 1920. However, Italians took it over from the withdrawing Greek troops on October 22, 1922, according to the Armistice of Mudanya. Finally, Turkish forces entered Silivri on November 1, 1922. It was part of Çatalca province between 1923–1926 and was bounded to Istanbul Province in 1926. It was enlarged with joining of Gümüşyaka (formerly Eski Ereğli) village from Çorlu district.