The civilians traveled by bus and plane through Russia and Belarus, following a deal brokered by US first lady Melania Trump.
Ukrainian authorities imposed restrictions on disclosing the number of evacuees or the border crossing location. The measures are to safeguard those who chose to remain in Oleshky as well as to protect future humanitarian missions, the organisers said.
The ceasefire in Ukraine's southern Kherson region, which began at 3am local time on Tuesday, is expected to continue through to Sunday evening. The estimated 2000 remaining residents of Oleshky were offered the choice of traveling to Ukrainian- or Russian-held territory, or remaining in the city with replenished food and medical supplies.
Those who chose to return to Ukraine were taken to the Russian city of Anapa then flown to Homel in Belarus, from where they proceeded back home.
Relatives waited on Saturday at the Ukrainian-Belarusian border, along with aid tents, coffee stands and even provisions to feed the pets the evacuees were bringing with them. Volunteers from organisations, including the Red Cross, Doctors without Borders and the World Central Kitchen, were also there.
Liza Paliy, 19, who last saw her father over two-and-a-half years ago when she, her mother and sister fled from the occupied territory while he stayed behind, was among those waiting.
"We thought at that time that it would be a month, two maximum, and we would return, but unfortunately, two years have already passed," she said.
Daria Pavlyn also waited at the border in hopes of reuniting with her father, Mykhailo, whom she had not heard from in about a month.
He had planned to flee occupied territory with his family after a nearby strike killed two neighbours but stayed behind when arrangements to care for the family's home and animals fell through.
"We realised that, well, there was no (other) way, and he walked us to the road and that was it - that was the last time" they saw him, Pavlyn said.
She said that since then, he had feared making the arduous journey out, particularly without Russian documents.
Russia's ombudswoman and lead representative on the mission, Yana Lantratova, said buses also transported Oleshky residents who wanted to live in Russia. Russian media outlets on Saturday showed civilians arriving at a temporary accommodation site in Simferopol on the Ukrainian peninsula of Crimea, which Moscow annexed in 2014.
Russia and Ukraine have not specified how many people chose to leave the city, but the US first lady posted on social media Friday that the humanitarian convoy could safely evacuate more than 750 people.
Apart from Melania Trump, Pope Leo XIV - the first American pontiff - also pressed Russian and Ukrainian leaders to allow aid deliveries and civilian evacuations.
Ukrainian President Volodymyr Zelenskiy on Saturday welcomed US approval of Ukraine's purchase of 500 PAC-3 Patriot interceptors but urged partners to supply the weapons from existing stocks to protect the country this winter, warning the newly authorised US sale could take years to deliver.
"Right now, the Russians are attacking our energy infrastructure every single day. In just these past two weeks of October, there have already been more than 30 Russian strikes on critical parts of our power grid," Zelenskiy wrote on X.
The Trump administration said Friday that it had approved a proposed $2.1 billion sale of Patriot air defence interceptors, after Kyiv had accused the Pentagon of delaying deliveries of the vital munition needed to stop Russian ballistic missiles.
The US State Department said 500 Patriot missiles would be purchased for Ukraine with donations from Canada, Germany and Norway through a US program and that no American funds were involved.
