An emerging challenge for nanoscale measurements is to capture and quantify the magnitude of structural changes in response to environmental changes. Certain environmental parameters can affect the nanoscale morphology of samples, such as changing the pH, solvent polarity, ionic strength, and temperature. We prepared test platforms of n-octadecyltrichlorosilane ring nanostructures to study surface morphology changes at the nanoscale in selected liquid media compared to dry conditions in air. Particle lithography combined with organosilane vapor deposition was used to fabricate nanostructures of regular dimensions. Multi layer nanostructures of OTS were used as a test platform for scanning probe studies of solvent-responsive properties where the sides of designed ring structures expose a 3D interface for studying the interaction of solvents with molecular side groups. In dry, ambient conditions, nanostructures of OTS were first imaged using contact mode atomic force microscopy (AFM). Next, ethanol or buffer was introduced to the sample cell, and images were acquired using the same probe. We observed substantial changes in the lateral and vertical dimensions of the ring nanostructures in AFM topography frames; the sizes of the rings were observed to swell by tens of nanometers. Even after heat treatment of samples to promote cross-linking, the samples still evidenced swelling in liquid media. This research will have consequences for studies of the properties of nanomaterials, such as solvent-responsive organic films and polymers.