Nineteenth-century views of the Prince School reveal contrasts between the original design and current renovations and raise questions about the efficacy of the building's recycled persona for condominiums and commercial use. The simplicity and coherence of the two main brick stories are overwhelmed by the addition of a top-heavy attic roof, with its excess of windows, which replaces the clear lines of the original mansard. At ground level, the surviving single arched central entrance is flanked by two-story bay window shops, accessed by landscaped brick terraces. Despite these changes, the Prince School still characterizes George A. Clough's work as Boston's city architect.