The earliest houses in the district are examples of Greek Revival architectural style. These houses were constructed during the 1860s and 1870s, a time when Greek Revival had declined in other areas but was still popular in Starkville. Queen Anne Style became more popular from the 1880s to 1900, resulting in several houses constructed in this style during the time period. Some of the most visually significant buildings in the neighborhood were constructed between 1900 and 1920. These houses, constructed in Colonial Revival and Four Square styles, represent the prosperity of the Starkville area during the time period in their large structures and ornate features. In the 1920s, after World War I, Bungalow style became popular for a short time. However, by the mid 1920s, Late Gothic Style took over as most popular. Each of these styles is represented by one or more houses in the district, showcasing a wide variety of different styles and influences throughout the years of the neighborhood's development. There is also one house that is a mixture of Greek Revival, Italianate, and Gothic architectural styles and one structure that features Jacobethan Style, one of only a few buildings in this style in the state of Mississippi.
During the 1860s and 1870s, the district became a popular residential location for many prominent merchants and civic leaders in the area. Throughout its history, Greensboro has been the home of three mayors, two alderman, a judge, a sheriff, and a state legislator. Many historical leaders of business, education, and economic development have also called Greensboro home, giving the district an important history that extends beyond the architecture of its buildings. Many of the original houses of these leaders and political figures remain preserved today, keeping the history of the region alive for future generations. Both the structures and their historic residents make Greensboro Street significant, placing the district on the National Register of Historic Places.