Traditional Mediterranean viticultural systems are increasingly vulnerable to climate-change-induced aridification. To empower local stakeholders, this study introduces an integrated Smart Farming framework deployed on Lemnos Island, Greece, combining cloud-based Google Earth Engine (GEE) dashboards with statistical scripting in R. To resolve canopy-scale omission errors (53.6%) caused by traditional low-density vineyards, regional Random Forest classifications were spatially overlaid with official 2025 administrative parcel registries. The multi-scale architecture operates via a unified, single-click parcel query executing across three interconnected modules: a Scientific module extracting 40-year climate-vegetation datasets (1986–2025) to track biomass versus surface temperature (NDVI vs. LST) and ecosystem deficits versus leaf moisture (dEVI vs. NDWI); a Farmer module integrating on-demand Sentinel-2 soil-adjusted indices (SAVI, NDWI) with live "Hephestos" weather station telemetry; and an Academic Validation module cross-referencing satellite precipitation against National Observatory of Athens database. Results demonstrated robust annual precipitation alignment between CHIRPS and ground station records (R² = 0.51; annual variance 2.6%; absolute deviation 11.2 mm). Long-term time-series analysis via Bai–Perron structural change tests confirmed a significant shift breakpoint (in 2000) accompanied by decadal vegetative curve advances across cultivars. At the parcel scale, coupling satellite surface thermal thresholds (LST > 32°C) and canopy moisture deficits (NDWI < 0.02) with live weather station data (precipitation = 0 mm) reliably triggered automated, cultivar-specific water and heat stress diagnostics on the user console. This hybrid framework proves that integrating administrative boundaries with multi-temporal remote sensing, time-series statistics, and live ground telemetry delivers actionable climate resilience metrics for arid viticulture.