Sweet cherry (Prunus avium) production is a key agricultural sector in southern Kyrgyzstan. However, its long-term sustainability is challenged by soil degradation, climate variability, and outdated orchard management. This research evaluated cherry productivity in seven experimental plots across southern Kyrgyzstan and neighboring Uzbekistan by examining soil properties (humus content, pH, and macronutrient levels), climatic conditions, tree age, and applied production technologies. The results showed that orchards with higher soil organic matter and near-neutral pH, particularly those in Dosmat (4.83% SOM, pH 7.0) and Mady (2.57% SOM, pH 7.4), produced 16–18 kg of fruit per tree. Productivity declined in older orchards (>19 years) and at high-altitude sites. In contrast, the Vodil plot in Uzbekistan achieved the highest yield (32.25 kg/tree) despite low soil organic matter (0.88%), owing to intensive fertilization, drip irrigation, and modern pest control, demonstrating how advanced agrotechnologies can compensate for suboptimal soil conditions. Conversely, orchards with minimal fertilization and irrigation, such as Vishenka-Osh (2 kg/tree), experienced substantial yield losses, underscoring the importance of adequate nutrient and water inputs. Satellite imagery and remote sensing further enhanced the assessment by providing early detection of plant stress and pest outbreaks. Overall, the findings indicate that sustainable cherry production in mountainous regions depends on an integrated strategy that combines soil fertility management, altitude-appropriate climate adaptation, and precision agriculture. Broader adoption of remote sensing, GIS-based planning, and decision-support tools can significantly strengthen resilience to environmental stress and align local practices with global sustainability goals. This research offers practical guidance for farmers and a strategic foundation for scaling climate-smart cherry production across Central Asia.