Objective: Advances in sensor miniaturisation and computational power have served as enabling technologies for monitoring human physiological conditions in real-world scenarios. Sleep disruption may impact neural function, and can be a symptom of both physical and mental disorders. This study proposes wearable in-ear electroencephalography (ear- EEG) for overnight sleep monitoring as a 24/7 continuous and unobtrusive technology for sleep quality assessment in the community. Methods: Twenty-two healthy participants took part in overnight sleep monitoring with simultaneous ear-EEG and conventional full polysomnography (PSG) recordings. The ear- EEG data were analysed in the both structural complexity and spectral domains; the extracted features were used for automatic sleep stage prediction through supervised machine learning, whereby the PSG data were manually scored by a sleep clinician. Results: The agreement between automatic sleep stage prediction based on ear-EEG from a single in-ear sensor and the hypnogram based on the full PSG was 74.1% in the accuracy over five sleep stage classification; this is supported by a Substantial Agreement in the kappa metric (0.61). Conclusion: The in-ear sensor is both feasible for monitoring overnight sleep outside the sleep laboratory and mitigates technical difficulties associated with scalp-EEG. It therefore represents a 24/7 continuously wearable alternative to conventional cumbersome and expensive sleep monitoring. Significance: The ‘standardised’ one-size-fits-all viscoelastic in-ear sensor is a next generation solution to monitor sleep - this technology promises to be a viable method for readily wearable sleep monitoring in the community, a key to affordable healthcare and future eHealth.