This study was focused on measuring the properties of twenty-three commercially available coatings formulated for exterior wood applications. The coatings were characterized by measuring their surface tension, solid content, viscosity, pH, and glass transition temperatures (Tg). Additionally, the wetting properties of coating droplets on wood substrates were measured. The contact angle of solvent-based and water-based coatings were characterized on untreated southern yellow pine wood samples using high-resolution image analysis and the Young–Laplace solution. An innovative image processing technique for determining the average diameter of coating droplets on wood was developed, and an iterative method to calculate the average contact angle using the Young–Laplace solution was applied. The water-resistance of the coated wood samples was evaluated during one week of water immersion tests. In general, solvent-based coatings had significantly lower contact angles and water uptake than water-based coatings. Water-based paint samples had the largest average contact angle (81°), and solvent-based transparent penetrating stains had the smallest contact angle (13.9°). A strong correlation was observed between the coating water uptake and their surface tension and solid content.