Vladimir Donskoy, known as the Brave, was born forty days after the death of his father, who died of the plague. At the age of four, he lost his older brother Ivan and became the sole heir to his father's estate, which significantly increased in 1359 due to his uncle's will, Grand Duke Ivan the Red.

In 1364, after the death of the young Moscow prince Ivan the Small, ten-year-old Vladimir became the second most important figure in the Moscow princely house, following his cousin, Grand Duke Dmitry Donskoy. Vladimir spent his childhood and youth in Moscow under the guardianship of the Metropolitan of Kiev and all Rus, Saint Alexius. In 1369, at the age of 16, Vladimir Andreevich participated in the defense of Pskov against the knights of the Livonian Order.

In 1371, Grand Duke Dmitry Ivanovich granted Vladimir Andreevich the Dmitrov and Galich principalities. In the autumn of the same year, Vladimir married Elena, the daughter of the Grand Duke of Lithuania Olgerd. In 1372 or 1373, the Grand Duke of Tver, Mikhail Alexandrovich, attacked Dmitrov, plundered it, and took many people to Tver. In 1374, Vladimir Andreevich restored the stone Dmitrov Kremlin and built a tower over the main gates.

It is believed that during this time, Vladimir met with the venerable Sergius of Radonezh. In the same 1374, he built an oak Kremlin in Serpukhov. According to other sources, the construction was carried out by his boyar Yakov Yurievich Novosilets. Sergius founded the Vysotsky Monastery near Serpukhov.

Vladimir Andreevich participated in wars against Tver (1375), Ryazan (1385), Novgorod (1392), strengthening the Grand Duchy of Moscow and defending the independence of Russian principalities from the Horde and Lithuanian troops.

In 1380, Vladimir led the right-hand regiment in the Battle of Kulikovo and, together with the voivode D. M. Bobrok-Volynsky, commanded the ambush regiment, which decided the outcome of the battle in favor of the Russians. In the battle, 63 vassals of Vladimir Andreevich were killed.

In 1382, Tokhtamysh, uniting the White and Golden Hordes, took revenge for Mamai's defeat. Vladimir defeated one of the Tatar detachments near Volok-Lamsky, after which Tokhtamysh left the borders of the Moscow principality. Serpukhov and Dmitrov were plundered and burned.

Vladimir Andreevich quickly restored his principality. His main residence was in Moscow, in the area of "Three Hills." He controlled the Serpukhov region, Dmitrov and Galich enclaves. In the 1380s, Vladimir began minting his own coins.

In 1385, he led the Moscow army against the Ryazan troops but suffered defeat. In 1388, a son, Yaroslav, was born to Vladimir in Dmitrov, and the Boris and Gleb Monastery was founded. Vladimir also laid the city of Yaroslavl on the banks of the Protva River.

In 1388, a conflict arose between Vladimir and Dmitry Donskoy. Vladimir wanted to maintain the ladder order of inheritance, but Dmitry left the throne to his son Vasily. Vladimir went to Torzhok, but in 1390 he made peace with Vasily, renouncing claims to Dmitrov and receiving half of Volokolamsk and Rzhev.

Vladimir the Brave led the defense of Moscow during the raid of Khan Edigei in 1408 and founded the city of Maloyaroslavets in honor of his son Yaroslav.