This paper develops a comprehensive framework of Area Angle Monitoring (AAM) to monitor the stress of bulk power transfer across an area of a power transmission system in real-time. Area angle is calculated from synchrophasor measurements to provide alert to system operators if the area angle exceeds pre-defined thresholds. This paper proposes general methods to identify these warning and emergency thresholds, and tests a mitigation strategy to relieve the area stress when the area angle exceeds the threshold. In order to handle the limited coverage of synchrophasor measurements, this paper proposes methods to estimate phase angles for boundary buses without synchrophasor measurements, which extends the application of AAM. AAM is verified for a power transmission area in the Western Electricity Coordinating Council system with both simulated data and synchrophasor measurements recorded from real events. A utility deployment to test the framework for monitoring area angle with live-stream and recorded synchrophasor data is described.