Built as a stable for Jonathan Mason's Mount Vernon Street houses (BH18), 24 Pinckney Street went through an early stage as a grocery store before achieving its present configuration. William Ralph Emerson's fanciful design provides an eye-catching display of windows illustrating his well-known concern for natural lighting. He deeply recessed the paneled doors and all of the windows, using heavy muntins to ensure that the facade not be reduced to a series of blank geometric voids. The design derived from the Queen Anne style, now blunted by the monochrome paint scheme. The remodeling was done for New England author Thomas Bailey Aldrich, for whom Emerson later designed a summer home in Maine.
The upper end of Pinckney Street has other late-nineteenth-century additions, but the predominant character represents the early 1800s. Speculative builders constructed the rows of brick houses with modest Federal and Greek Revival detailing. Laid out at the end of the eighteenth century, the street includes a formerly freestanding house, number 17, built in about 1800; it is oriented perpendicular to the street, with its front yard preserved. Gridley J. F. Bryant acquired and remodeled it in 1856 with bold Italianate motifs characteristic of his work. The present Federal entrance is a late-twentieth-century replacement.