Grand Princess Anna Vasilievna of Ryazan (Russian: Анна Васильевна) (1451–1501) was a Russian noblewoman, Regent of the Ryazan Principality in 1483 and in 1500-1501, during the minority of her son and grandson. She was the only daughter of Grand Prince Vasily II of Moscow and the mother and grandmother of last Grand Princes of Ryazan Principality. Anna was born in Moscow to the family of Vasily II of Moscow, who was blinded five years before her birth during a time of troubles, and Maria Yaroslavna of Borovsk.
Before his death in 1456 Grand Prince Ivan Fyodorovich of Ryazan entrusted his friend Vasily of Moscow with temporary governing of the principality and taking care of his children Vasily and Theodosia until their maturity. But soon after Ivan's death Vasily of Moscow moved orphans to Moscow and appointed a voevoda to Ryazan. This decision started a process of joining of Ryazan Principality to the Grand Duchy of Moscow. Vasily II's heir Ivan III of Russia continued his father's policy towards Ryazan and Anna grew together with Ryazan prince Vasily.
When Anna grew up her mother has decided to marry Anna and Vasily. She asked her son Ivan III to delay annexation of Ryazan because it was not suitable to a Grand Princess to marry an ordinary nobleman even of princely descent. Ivan III agreed and allowed on Summer 1464 to return sixteen-year Prince Vasily to his family seat. But the same winter he came to Moscow to marry Anna and, after the wedding, the couple returned to Ryazan.
In 1467 Anna bore a son Ivan and until the death of her husband in 1483 did not participate in governing the principality and did not protest when her brother two times annexed Ryazan territories.
In 1483 Anna became the regent of her sixteen-year son. In her policy Anna tried to expand her domain, she visited often Moscow and due her diplomatic efforts the Pronsk principality was added to Ryazan. A major problem in Ryazan-Moscow relations was so-called ryazan ukraina, a huge steppe region in the basin of Don River. According to treaties, Ryazan was obliged not to settle in these lands, but many years Ryazan princes secretly colonized this area and during the Anna's regency this process become much more significant. Numerous immigrants received considerable privileges, being released for 3–7 years from taxes if agreed to remain in steppe for ever.