(1) Objective: To evaluate and compare the depth of cure (DOC) of two bulk-fill flowable composites (Filtek Bulk Fill Flowable Restorative and Tetric EvoFlow Bulk Fill), two conventional flowable composites (Filtek Supreme XTE Flowable Restorative and G-ænial Flo X) and one high-strength universal injectable composite (G-ænial Universal Injectable). (2) Methods: specimens were placed in a stainless-steel mold with an orifice of 4 mm in diameter and 10 mm in depth and light-cured for 20 s using a light emitting diode (LED) light-curing unit (LCU) with an irradiance of 1000 mW/cm²; depth of cure was assessed using the ISO 4049 scrape technique, and the absolute length of the specimen of cured composite was measured in millimeters with a digital caliper. The same procedure was repeated with 14 samples for each material under investigation, for a total number of 70 test bodies. Material roughness and hardness results were also investigated using, respectively, a 3D laser confocal microscope (LEXT OLS 4100; Olympus) at ×5 magnification and a Vickers diamond indenter (Vickers microhardness tester, Shimadzu^®, Kyoto, Japan) under 10-N load and a 30 s dwell time. SEM images at 3000 and 9000 magnification were collected in order to study the materials’ filler content. Statistical analysis were performed by a commercial statistical software package (SPSS) and data were analyzed using multiple comparison Dunnett’s test. (3) Results: The average DOC of both bulk-fill composites was more than 4 mm, as a range of 3.91 and 4.53 mm with an average value of 4.24 and 4.12 mm, while that of the conventional flowable composites was much lower, as a range of 2.47 and 2.90 mm with an average value of 2.58 and 2.84 mm; DOC of the high-strength injectable composite was greater than the one of traditional composites, but not to the level of bulk-fill materials, as a range of 2.82 and 3.01 mm with an average value of 3.02 mm. Statistical analysis revealed significant differences (p-values < 0.05) in the depth of cure between bulk fill flowable composites and other composites, while there was no difference (p-values > 0.05) between the materials of the same type. (4) Conclusions: Bulk-fill flowable composites showed significantly higher depth of cure values than both traditional flowable composites and high-strength injectable composites.