In 2008, the Israeli human rights group Yesh Din successfully petitioned the Supreme Court to remove all the homes, on the basis that they were built on land owned by local Palestinians.
But new US President Donald Trump has pledged strong support for Israel, and his aides are more sympathetic to the settlement plan.
The worldwide community considers all Jewish settlements in the West Bank illegal, and the United Nations condemned construction plans last week.
Amona is the largest of about 100 unauthorised outposts erected in the West Bank without permission but generally tolerated by the Israeli government.
A Supreme Court ruling, which sided with the Palestinian claimants, ended months of attempts by government hardliners to legalize the outpost, instead ordering it to be evacuated by February 8.
The eviction operation came as Israel approved the construction of 3,000 new settlement homes at other locations in the West Bank. According to reports, several police were injured when protesters set off devices that spread pepper spray around, while at least one border guard refused to escort a family out of a house.
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Under the new law, settlers could remain on the land if they built there without prior knowledge of Palestinian ownership or if homes were constructed at the state's instruction.
Minor scuffles broke out between some activists and police as protesters tried to block officers from progressing.
"Thanks to the campaign in Amona, thousands of families will be rescued from being evicted from their homes".
The Palestinians claim both areas, occupied by Israel in the 1967 Middle East war, as parts of a future state. On the same date in 2006, Israeli police demolished nine homes in the outpost in a bid to evacuate the settlers. Though worldwide law terms these settlements as illegal, the Israeli government had contended this.
We once again warn against any unilateral actions that can be an obstacle to a negotiated two-State solution and call on both parties to return to meaningful negotiations on the basis of relevant Security Council resolutions, and in accordance with global law, in order to address all final-status issues.