Experimental studies of dropwise condensation have generally indicated that higher heat transfer coefficients correspond to smaller mean sizes for droplets growing through condensation on the surface. Recent investigations of dropwise condensation on nanostructured surfaces suggest that optimizing the design of such surfaces can push mean droplet sizes down to smaller values and significantly enhance heat transfer. This paper summarizes a theoretical exploration of the limits of heat transfer enhancement that can be achieved by pushing mean droplet size to progressively smaller sizes. A model analysis is developed that predicts transport near clusters of water droplets undergoing dropwise condensation. The model accounts for interfacial tension effects on thermodynamic equilibrium and noncontinuum transport effects, which become increasingly important as droplet size becomes progressively smaller. In this investigation, the variation of condensing heat transfer coefficient for droplet clusters of different sizes was explored for droplet diameters ranging from hundreds of microns to tens of nanometers. The model predictions indicate that the larger droplet transport trend of increasing heat transfer coefficient with decreasing mean droplet size breaks down as droplet size becomes smaller. The model further predicts that as drop size becomes smaller, a peak heat transfer coefficient is reached, beyond which the coefficient drops as the size continues to diminish. This maximum heat transfer coefficient results from the increasing importance of surface tension effects and noncontinuum effects as droplet size becomes smaller. The impact of these predictions on the interpretation of dropwise condensation heat transfer data, and the implications for design of nanostructured surfaces to enhance dropwise condensation are discussed in detail.