While brick and stone houses of the late nineteenth and early twentieth centuries predominate along W. Main Street, there are some earlier buildings. This three-bay, two-story brick house on a high basement was built for James P. Carroll, an affluent minister and hymn writer. It is a transitional building with windows that are Greek Revival in both their form and large size but with the small panes and the stuccoed lintels above the first-floor openings that hark back to Federal design. The entrance is sheltered by a one-story, central, pedimented Doric portico. This house and the Alderson House (c. 1850; 113 W. Main), with its Doric frontispiece, are local versions of mid-nineteenth-century housing with touches of style from pattern books.

Opposite, Lebanon Middle School (1940; 131 W. Main), built as the town's high school, is a two-story brick Colonial Revival building with a pedimented two-story central portico and a multitiered cupola. It sits on a nine-acre campus.