From the late 1860s through the end of the century, the Hunnewells commissioned houses for seven of their eight children and their families on the five-hundred-acre property. These included both new buildings and substantial colonial farmhouses that were remodeled. In 1871, John Hubbard Sturgis designed The Cottage (848 Washington Street), one of the earliest examples of Queen Anne architecture in the United States, varied in plan, massing, and materials to create a highly picturesque effect. This building was used by several sets of Hunnewell newlyweds while waiting for their permanent residence to be completed. In 1875, Henry Van Brunt provided a Stick Style design for the Walter Hunnewell House (37 Pond Street, Natick), which was remodeled and enlarged by Stanford White in 1881. Beginning in 1883, H. H. Hunnewell turned for architectural services to Shaw and Hunnewell (the firm of his son-in-law and son) for the remaining work on the estate. They designed Hill Hirst for the Robert Gould Shaws (1883–1884, 82 Pond Road, Natick) and The Oaks for the Arthur Hunnewells (1891, replacing an 1871–1873 house by John H. Sturgis destroyed by fire, 866 Washington Street, Wellesley; extensively remodeled 1937), both in the Queen Anne style. In 1894 they designed The Pines (828 Washington Street) in a Georgian Revival manner to replace an earlier house of the same name. In 1888–1891, Henry Sargent Hunnewell designed his own house, The Cedars (110 Pond Road, 1930s replaced, Frank Sewell Owens). H. S. Hunnewell, with some advice from Charles Eliot, also developed the grounds of The Cedars, a landscape as sophisticated for its time as his father's had been for midcentury. Although some of these buildings have become the property of Wellesley College (
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), many are still owned by Hunnewell descendants. With the controlled landscape, gatehouses, and other outbuildings, the estates still maintain much of their turn-of-the-twentieth-century character.