Designing remote health monitoring systems requires a multi-faceted perspective that takes into account requirements and contexts imposed by the medical application, technology, and end-user. We study such a design perspective in the context of remote and real-time edema monitoring. Edema (accumulation of fluid in certain soft-tissues) is regarded as one of the most important symptoms for systematic diseases such as heart failure. Monitoring edema allows patients and caregivers to understand the state of sickness and effectiveness of the treatments. This article proposes a novel low-power context-aware and real-time wearable platform capable of continuous assessment of ankle edema in remote settings. Our system keeps track of changes in subject’s ankle circumference as well as current body posture. An examination of our system with 15 subjects demonstrates the effectiveness and reliability of the proposed force-sensitive-resistor-based edema sensor (with an R2 of 0.87 for our regression model and intra-class correlation of 0.97) as well as an over 96 percent accuracy in activity monitoring that provide the means to perform reliable data validation on ankle circumference measurements in a continuous manner. Furthermore, we devise a novel derivative-free power optimization approach to maximize the battery lifetime resulting in improvement in battery lifetime by a factor of 2.13.