A wheeled gate support is described herein. The wheeled gate support includes a front wheel in-line with a rear wheel, one or more side frames, and a post. The one or more side frames assemble to opposing sides of the wheels. The post has a bottom portion and a top portion. The bottom portion assembles to the one or more side frames to form a pivot point and the top portion is configured to assemble to one or more gate rails of a gate. The wheels can therefore pivot about the pivot point while rolling along the ground to assist a user with opening and closing a gate along rough or bumpy terrain. A wheeled gate support kit is also provided.