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In 1904, Alfred Yeomans was called upon by his uncle, Pennsylvania industrialist James Boyd I, to create a landscape plan for Boyd’s estate, Weymouth, in Southern Pines. Following that commission, Yeomans worked extensively in the region, including plans for the Weymouth Heights and Knollwood subdivisions. Again, working for the Boyd family, Yeomans designed the Weymouth Heights subdivision beginning in 1913. While Yeoman’s original schematic designs for individual lots and gardens appear to be largely unrealized, the subdivision’s tree-lined, curvilinear roads and generous lots with houses set back from the street are a departure from the orthogonal street grid often utilized in early town development. Yeoman’s work is most clearly visible in the undulating extension of Massachusetts Avenue, the gentle curve of Indiana Avenue and what is now Highland Road. The subdivision also includes a large array of mature trees, many of which are longleaf pines in old-growth forest.