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Abstract Medicanes are cyclones with tropical characteristics in the Mediterranean basin. They typically show an eye with neighboring spiraling bands, but the surrounding region of maximum winds is not well documented, especially near the sea surface, due to limited available observational data. Estimating such characteristics accurately is essential for a better understanding of the specific fine‐scale wind structures and their relationship with the development mechanisms of medicanes. Here we first demonstrate the capacity of synthetic aperture radar (SAR) spaceborne instruments to diagnose important medicane structural characteristics. Building on an unprecedented collection of SAR high‐resolution observations and subsequent sea‐surface wind‐speed estimates, the eye patterns, heavy rainfall, convective cells, and boundary‐layer roll vortices are evidenced, with attributes comparable with those of tropical cyclones of similar intensities. Motivated by this resemblance, we estimate parameters characterizing the cyclone surface wind structure (the intensity, inner and outer size, and Rossby number) from high‐resolution observations of medicanes. We show that their inner size is of magnitude comparable with that of tropical cyclones of similar intensities. Conversely, typical outer sizes and Rossby numbers are found to be smaller. The misrepresentation of these characteristics in medium‐resolution global reanalyses brings into question their suitability and the application of diagnostic tools to these data to monitor the life cycles of medicanes. This invites us to develop dedicated observation‐based monitoring frameworks. Medium‐resolution scatterometers provide more reliable structural estimates despite the small medicane size. Along with SAR surface wind‐speed estimates, and complemented by upper‐level measurements, they may support future reanalysis efforts. Further investigation is needed to understand how the high‐resolution features reported in our work connect with kilometer‐ and subkilometer‐scale physical processes.