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Street-level imagery contains personally identifiable information (PII), some of which is context-dependent. Existing anonymization methods either over-process images or miss subtle identifiers, while API-based solutions compromise data sovereignty. We present an agentic framework CAIAMAR (\underline{C}ontext-\underline{A}ware \underline{I}mage \underline{A}nonymization with \underline{M}ulti-\underline{A}gent \underline{R}easoning) for context-aware PII segmentation with diffusion-based anonymization, combining pre-defined processing for high-confidence cases with multi-agent reasoning for indirect identifiers. Three specialized agents coordinate via round-robin speaker selection in a Plan-Do-Check-Act (PDCA) cycle, enabling large vision-language models to classify PII based on spatial context (private vs. public property) rather than rigid category rules. The agents implement spatially-filtered coarse-to-fine detection where a scout-and-zoom strategy identifies candidates, open-vocabulary segmentation processes localized crops, and $IoU$-based deduplication ($30\%$ threshold) prevents redundant processing. Modal-specific diffusion guidance with appearance decorrelation substantially reduces re-identification (Re-ID) risks. On CUHK03-NP, our method reduces person Re-ID risk by $73\%$ ($R1$: $16.9\%$ vs. $62.4\%$ baseline). For image quality preservation on CityScapes, we achieve KID: $0.001$, and FID: $9.1$, significantly outperforming existing anonymization. The agentic workflow detects non-direct PII instances across object categories, and downstream semantic segmentation is preserved. Operating entirely on-premise with open-source models, the framework generates human-interpretable audit trails supporting EU's GDPR transparency requirements while flagging failed cases for human review.