In this study, the recovery of polyphenols from olive oil mill and winery waste was investigated. The performance of ultrasound assisted extraction (UAE), microwave assisted extraction (MAE), and pressurized liquid extraction (PLE) was assessed using ethanol–water mixtures, which are compatible with food, nutraceutical, and cosmetic applications. The extraction efficiency from olive pomace and lees samples was evaluated in terms of total polyphenol content (TPC), determined by high performance liquid chromatography (HPLC) and Folin–Ciocalteu assay. The effect of solvent composition, temperature, and time was analyzed by response surface methodology. Ethanol:water 50:50 (v/v) was found to be a suitable solvent mixture for both kinds of samples and all three extraction techniques. The performance of the extraction techniques was evaluated, under optimal experimental conditions, with a set of different representative samples of residues from olive oil and wine production. Overall, the best extraction efficiency for olive pomace residues was provided by MAE (ethanol:water 50:50 (v/v), 90 °C, 5 min), and for wine residues by PLE (ethanol:water 50:50 (v/v), 100 °C, 5 min, 1 cycle). However, the results provided by UAE (ethanol:water 50:50 (v/v), 30 min) were also suitable. Considering not only extraction performance, but also investment and operational costs, UAE is proposed for a future scaling up evaluation. Regarding olive pomace as a source for natural phenolic antioxidants, olive variety and climatic conditions should be taken into account, since both influence TPC in the extracts, while for winery residues, lees from red wines are more suitable than those from white wines.