We present a multi-wavelength study of galaxy populations in the core of the massive, X-ray luminous cluster XMMU J2235 at z=1.39, based on VLT and HST optical and near-infrared photometry. Luminosity functions in the z, H, and Ks bands show a faint-end slope consistent with being flat, and a characteristic magnitude M* close to passive evolution predictions of M* of local massive clusters, with a formation redshift z>2. The color-magnitude and color-mass diagrams show evidence of a tight red sequence of massive galaxies, with overall old stellar populations, generally early-type morphology, typically showing early-type spectral features and rest-frame far-UV emission consistent with very low star formation rates (SFR<0.2Msun/yr). Star forming spectroscopic members, with SFRs of up to ~100Msun/yr, are all located at clustercentric distances >~250kpc, with the central cluster region already appearing effectively quenched. Massive galaxies in the core of this cluster appear to be in an advanced evolutionary stage in terms of both star formation and mass assembly. The high-mass end of the galaxy stellar mass function is essentially already in place, and the stellar mass fraction estimated within r500 (~1%, Kroupa IMF) is already similar to that of local massive clusters. On the other hand, morphological analysis of the massive red sequence galaxies suggests that they are smaller than similarly massive local early-types. While possibly affected by systematics and biases, this result might imply that, in spite of the overall early assembly of these sources, their evolution is not complete, and processes like minor (and likely dry) merging might still shape their structural properties to resemble those of their local counterparts, without substantially affecting their stellar mass or host stellar populations.[abridged] Comment: 14 pages, 9 figures, accepted for publication in Astronomy & Astrophysics