The demolitions of Palestinian homes, most of which were still under construction, drew condemnation from the European Union and UN officials.
Israel says the homes south of Jerusalem were built too close to its separation barrier cutting off the occupied West Bank, posing a security risk, and the demolitions were approved by its supreme court following a lengthy process.
Palestinian leaders expressed outrage at the demolitions in the Sur Baher area, which straddles the occupied West Bank and Jerusalem.
They note that most of the buildings were located in areas meant to be under Palestinian Authority civilian control under the Oslo accords of the 1990s.
Before dawn Monday, hundreds of Israeli police and soldiers sealed off buildings in the area while residents and activists were dragged out.
A statement from Israeli defence ministry unit COGAT said "12 buildings and two building foundations were demolished," adding that they were "built illegally".
Israel's supreme court "ruled that the buildings may be demolished as they constitute a security danger to the area of the security fence," the statement said.
UN humanitarian agency OCHA said a preliminary assessment showed 24 people, including 14 children, were displaced.
More than 300 people were affected by the demolitions, it said.
Prior to the demolitions, OCHA said the buildings were to include some 70 apartments. It said those being displaced were from three households.
On June 18, a 30-day notice was given by Israeli authorities informing of their intent to demolish the buildings.
Residents fear another 100 buildings in the area in a similar situation could be at risk in the near future.
Israel occupied the West Bank and east Jerusalem in the 1967 Six-Day War. It later annexed east Jerusalem in a move never recognised by the international community.
It began construction of the separation barrier during the bloody second Palestinian intifada, or uprising, in the early 2000s and says it is necessary to protect against attacks.
Palestinians see it as an "apartheid wall" and a potent symbol of the Israeli occupation.