Kenya’s land sector stands at an inflection point. With 60–90% of rural land undocumented and urban informal settlements housing millions without formal tenure, traditional surveying methods cannot meet the scale of demand. Simultaneously, the Ministry of Lands has committed to Artificial Intelligence (AI) and Machine Learning (ML) as core tools for modernizing land administration. This article examines the convergence of two technological frontiers—advanced drone systems and agentic AI—and their transformative potential for the Land & Built Environment domain in Kenya. While drone adoption for aerial mapping is accelerating through initiatives like KISIP2 and the Konza National Drone Corridor, the next leap requires moving beyond passive data capture toward autonomous, decision-executing systems. Drawing on Kenyan case studies from Murang’a, Kajiado, and Konza Technopolis, this paper proposes a framework for deploying agentic AI–piloted drones capable of autonomous survey missions, real-time adjudication, and dynamic urban planning. It addresses technical requirements, regulatory pathways, and capacity-building imperatives, arguing that agentic systems offer Kenya a once-in-a-generation opportunity to leapfrog incremental digitisation and achieve fully autonomous land administration.