99 Main Street is more than a very handsome building commanding the harbor front. It is an icon of simplicity. Erected in the 1790’s shortly after a destructive fire, the building had commercial shops on the ground floor and residential uses on the upper story.
Architecturally, the edifice makes a singular statement. The proportions are simple and direct—the building’s configuration can be understood in a single glance. Note how the exterior walls directly support the roof and the roof ridge spans straight between the two end wall chimneys.
The reserved building silhouette is only the first impression. A closer look reveals elegant craftsmanship and details. The proportion of the windows is thoughtful and orderly. Notice how the windows graduate in size from larger on the first floor to smaller at the top floor. The two brick belt courses that wrap around the building provide a subtle horizontal articulation and echo the corner location at Green Street. The wood cornice is a beautiful dentil and modillion trim popular in Annapolis at the time. Dentil trim is so named because of the visual similarity to teeth. Modillion trim has repetitive small projecting brackets that originated in Greek architecture. The attractive Flemish bond brick pattern, the dramatically angled flat window arches, and tall thin chimneys further reflect the superior building craft achieved in late 18th century Annapolis.
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