The shortwave downward solar irradiance (SDR) is an important factor that drives climate processes and energy production and can affect all living organisms. Observations of SDR at different locations around the world with different environmental characteristics have been used to investigate its long-term variability and trends at different time scales. Periods of positive trends are referred to as brightening periods and of negative trends as dimming periods. In this study we have used 30 years of pyranometer data in Thessaloniki, Greece, to investigate the variability of SDR under three types of sky conditions (clear-, cloudy- and all-sky). The clear-sky data were identified by applying a cloud screening algorithm. We have found a positive trend of 0.38%/year for all-sky, ∼0.1%/year for clear-sky, and 0.41%/year for cloudy conditions. The consistency of these trends, their seasonal variability, and the effect of the solar zenith angle have also been investigated. Under all three sky categories, the SDR trend is stronger in winter, with 0.7, 0.4, and 0.76%/year, respectively, for all-, clear-, and cloudy-sky conditions. The next larger seasonal trends are in autumn—0.42 and 0.19%/year, for all and cloudy skies, respectively. The rest of the seasonal trends are significant smaller, close to zero, with a negative values in summer, for clear and cloudy skies. The SDR trend is increasing with increasing solar zenith angle, except under cloudy skies, where the trend is highly variable and close to zero. Finally, we discuss shorter-term variations in SDR anomalies by examining the patterns of the cumulative sums of monthly anomalies from the climatological mean, both before and after removing the long-term trend.