Condensation is an important process in both emerging and traditional power generation and water desalination technologies. Superhydrophobic nanostructures promise enhanced condensation heat transfer by reducing the characteristic size of departing droplets via coalescence-induced shedding. In this work, we investigated a scalable synthesis technique to produce functionalized oxide nanostructures on copper surfaces capable of sustaining superhydrophobic condensation and characterized the growth and departure behavior of the condensed droplets. Nanostructured copper oxide (CuO) films were formed via chemical oxidation in an alkaline solution resulting in dense arrays of sharp CuO nanostructures with characteristic heights and widths of ≈1 μm and ≈300 nm, respectively. To make the CuO surfaces superhydrophobic, they were functionalized by direct deposition of a fluorinated silane molecular film or by sputtering a thin gold film before depositing a fluorinated thiol molecular film. Condensation on these surfaces was characterized using optical microscopy and environmental scanning electron microscopy to quantify the distribution of nucleation sites and elucidate the growth behavior of individual droplets with characteristic radii of ≈1–10 μm at supersaturations ≤1.5. Comparison of the measured individual droplet growth behavior to our developed heat transfer model for condensation on superhydrophobic surfaces showed good agreement. Prediction of the overall heat transfer enhancement in comparison to a typical dropwise condensing surface having an identical nucleation density suggests a restricted regime of enhancement limited to droplet shedding radii 2.5 μm due to the large apparent contact angles of condensed droplets on the fabricated CuO surfaces. The findings demonstrate that superhydrophobic condensation typified by coalescence-induced droplet shedding may not necessarily enhance heat transfer and highlights the need for further quantification of the effects of surface structure on nucleation density and careful surface design to minimize parasitic thermal resistances.