A display apparatus is provided. The display apparatus includes: a video processor which, in a multi-view mode, processes a plurality of contents and generates a plurality of content views, a display which displays the plurality of content views, a sync signal generator which generates a sync signal regarding the plurality of content views, a communicator which transmits the sync signal, and a controller which, upon communicating with a glasses apparatus, transmits information on a target content view which is controllable from among the plurality of content views to the glasses apparatus. Accordingly, a newly-connected glasses apparatus may be directly synchronized with a target content view.