Set well back from the road, this house faces generally to the southeast— The rear elevation overlooks an open expanse of lawn and the gazebo is set within a small grove of trees to the northwest.

29 Fairgrounds Road is a long, two-story house with several one-story additions. Sheathed in brick and prefabricated wood panels, it utilizes irregular groupings of windows and cantilevered projections of the second floor in its horizontally massed design. There are open screened porches on the right of the facade and at the rear. The latter porch is joined to a greenhouse.

This modern well-preserved house was designed by Douglas William Orr (1892-1966), a major architect who practiced in New Haven from 1919 until his death. Born in Meriden, Connecticut, he was educated at Yale. The International-style design for this house represented quite a departure for Orr, who for most of his career specialized in the Colonial Revival and Art Deco styles. It was built for Sumner McKnight Crosby, a professor of art history at Yale University, and is still owned by the family. LeRoy Fraser, a developer in Woodbridge, who laid out this subdivision in the late 1920s, sold the lot to Crosby in 1940. Although much of his development encompassed the old site of the annual Woodbridge-Bethany agricultural fair, this property had belonged to 'Morris F. Tyler and it still contains a barn associated with his estate, as well as an unusual landscape feature, now a gazebo at the rear of the house. The structure was once the cupola of the Lyceum at Yale, which was built in 1804 on the old campus and demolished in 1901. At the time Tyler was the Yale treasurer and he rescued the cupola and had it brought here by horse and wagon.