Hillcrest was first settled in the 1840's by Robert John Turner, a reformer from England. The Turner house, named "Bracondale", stood where Hillcrest Park is today.

By 1884, a small village grew up on the edge of the Turner estate, at the intersection of Christie and Davenport. This settlement became known as Bracondale Village. The Village consisted mostly of farmers and a few stores. Its first postmaster was Frank Turner, the son of Robert Turner.

In 1909, Bracondale Village was annexed by the City of Toronto. Shortly thereafter, Frank Turner's heirs subdivided the Bracondale estate and turned it into an exclusive subdivision named " Bracondale Hill Park".

The Turner family retained ownership of the Bracondale house until 1937, when it was sold to the City and demolished in order to make room for Hillcrest Park.