A lateral periodontal cyst (LPC) is a rare finding. Patients diagnosed with LPC younger than 40 years of age are not that common. Mostly asymptomatic LPCs can be discovered on routine radiographs as an oval radiolucency between two mandibular premolar teeth roots and can vary in shape and size. Most cases are treated with enucleation, bone curettage, or a combination of both, greatly depending on the surgeon’s preference. Because most LPCs are quite small, lesions do not require any regenerative procedures. In the presented case, because of cortical expansion of the lesion and loss of vital bone bridge surrounding two adjacent maxillary teeth, a guided bone regenerative procedure (GBR) with xenograft bone substitute was used. Despite that small lesions can heal on their own, nowadays the approach of full-mouth therapy (FMT), including direct soft or hard tissue reconstruction in the oral cavity, seems to be a wise treatment. The presented paper presents and describes an unusual LPC case with cortical bone expansion in a very rare maxillary canine–premolar region.