Returning to the right side of the street, the Frazier-Greenleaf House, built prior to 1790, was originally a two-story house. The second owner, Col. John Greenleaf added the third floor and mansard roof in 1811. John Quincy Adams courted Mary Frazier here while he was studying law with the famous Newburyport jurist Theophius Parsons in the late 1780's. Miss Frazier rejected Adam's advances, however, because her family and friends felt that his prospects were "none to good."

The Swain-Doyle House at No. 30 Green Street, across the street, is a typical Federal period house in wood, built in 1808. Important features to note are the decorative caps over the windows, the enriched classical cornice just below the roof, and the railing around the roof, which helps to hide the shallow slope of the roof. The Ionic porch was a later addition. Standing here, you can see elements of the three orders (or styles) of Greek architecture on the porches of No. 32 - Doric; No. 30 - Ionic; and No. 37 Corinthian.

The next house, the Bradbury-Spalding House, has a gambrel roof and five windows across the front, typical of the mid to late 18th century Georgian house. The doorway looks like a miniature classical temple, with Doric pilasters supporting an entablature and triangular pediment. An entablature is one of the two elements of a classical order, the other element bring the column on which it rests, It is the horizontal member, here decorated with triglyphs (three vertical channels) and metopes (the blank spaces in between). You can see here that the pediment is made up of three cornices in the shape of a triangle. Also note the pediments over the dormer windows.

The house was built after 1786 by Theophilus Bradbury, a member of Congress during Washington's administration and a justice of the Massachusetts Supreme Court in 1797. Under Spalding ownership, many literary and professional people gathered here; and the Spalding women tutored local students for college in the Spalding School. Another distinguished owner was Wallace Nutting, the well-known authority on antiques.