Wintertime sea surface heat flux variability across the Kuroshio Extension (KE) front is analyzed using data from the Kuroshio Extension Observatory (KEO) buoy in the Kuroshio recirculation gyre south of the KE front and from the Japan Agency for Marine-Earth Science and Technology KEO (JKEO) buoy in the north of the front. The coincident data used are from periods during two winters (2007 and 2008), when both buoys had a complete suite of meteorological data. In these two winter periods, the focus of this research is on three types of typical weather patterns referred to here as the northerly wind condition, the monsoon wind condition, and the normal condition. During the northerly wind condition, latent and sensible heat fluxes were large and often varied simultaneously at both sites, whereas during the monsoon wind condition the latent heat flux at the KEO site was significantly larger than that at the JKEO site. The difference between these heat flux patterns is attributed to the different airmass transformations that occur when prevailing winds blow across the KE front versus along the front. Reanalysis products appear to reproduce these heat flux spatial patterns at synoptic scales. It is suggested that the relative frequencies of these different types of weather conditions result in anomalous spatial patterns in the heat fluxes on monthly time scales.