Waste-grade cork samples of Quercus cerris were subjected to maceration extraction using 7 different solvents, including pure water (I), pure acetone (II), 75% aqueous ethanol (III), 75% aqueous methanol (IV), 75% aqueous acetone (V), 50% aqueous acetone (VI), and 25% aqueous acetone (VII). The extract yields, extract compositions, as well as antioxidant and antimicrobial activities of the extracts were analyzed. The results showed that maceration extraction was highly efficient, particularly with binary solvents resulting in up to 6% extract yield and up to 488 mg GAE/g extract total phenolic content. The extracts exhibited a variable antioxidant activity determined by DPPH and FRAP methods as well as antimicrobial activity against gram-positive bacteria and fungus determined by agar diffusion test. The CIELAB color parameters of extracts were correlated with maceration time, and the correlation was highest with pure water extracts. The FT-IR spectra of acetone-extracted cork revealed six key markers of phenolic compounds with the presence of peaks at approximately 2920 cm−1, 2850 cm−1, 1609 cm−1, 1517 cm−1, 1277 cm−1, and 1114 cm−1. The overall results suggest that the maceration of waste cork in binary solvents and pure acetone are green alternatives to conventional Soxhlet extraction for the production of polar extracts.