They were met by burning barricades, acrid smoke and spikes on the road in the settlement of Sanur, however burning tyres were soon extinguished and unarmed police were seen cutting wire next to the gates and entering.
The first settlers surrendered with little protest and began leaving on buses.
However there have been scenes of emotion with women breaking down in tears at the side of the road as police began pulling down rows of tents pitched near the main gate.
The West Bank operation comes after Israel finished evacuating all Jewish settlements in Gaza, in an historic pullout from land where Palestinians want a state.
Some 8,500 Jews had settled in the strip, home to 1.4 million Palestinians.
“Right now there are no Israeli settlements in the Gaza Strip,” said Maj-Gen Dan Harel.
In Netzarim, the last settlement to be evacuated, soldiers joined settlers in two hours of tearful prayers.
Then, men hugged each other and set off on a mournful last procession carrying on their shoulders the large candelabra, or menorah, they removed from the synagogue.
The Gaza evacuations took two weeks less than expected.
After the Gaza pull-out, the Israeli and Palestinian leaders spoke by phone – their first conversation for two months.
Palestinian President Mahmoud Abbas phoned Israeli Prime Minister Ariel Sharon to say he hoped the pullout would open a new page in relations and the two agreed to meet soon, Mr Sharon’s office said in a statement.
The two last met on June 21.
Mr Abbas called the withdrawal a “brave and historic decision,” the Israeli statement said.
US President George W Bush hailed the Gaza evacuation as an “historic step” that would bolster the search for peace in the Middle East.
At the behest of President Abbas, militants largely held their fire during the pullout.
Tens of thousands of Palestinians celebrated the evacuation at a Hamas rally late on Monday.
Clashes are expected at Sanur and Homesh, two of the four West Bank settlements yet to be cleared.
Pullout opponents had expressed plans to make the two remaining West Bank withdrawals so traumatic it will be much harder to ever consider giving up more settlements in the territory where Israelis see a much stronger biblical claim than to tiny Gaza.
Mr Sharon says further withdrawals will only come through talks with the Palestinians, which in turn depend on militants being disarmed under a US-backed “road map.” Israel has failed to meet its own road map commitment to freeze settlement building.
Approximately 3.8 million Palestinians live in the West Bank and Gaza.