Beginning in 1896, sculptor Daniel Chester French made his summer home on this 122-acre property west of Stockbridge. Over the course of 44 years, he created a country estate that included a residence, two studios, an old barn, garden walks, and a tennis court. The Colonial Revival house, designed by Henry Bacon in 1901, was sited within a Beaux Arts site plan to take advantage of views of Monument Mountain and Mount Everett.
In 1898, French built his studio with a graveled terrace furnished with wicker chairs, Mexican ceramic urns, and plants in decorative planters. In an adjacent fruit orchard he created a garden, where straight walks divide the garden geometrically: the cross-axis is flanked by the studio, while the main axis terminates in a wrought-iron arch and a pair of white-glazed, terra cotta columns which mark the beginning of a woodland walk. Enclosed by a lilac hedge and hemlocks, the garden also included a pergola, marble benches, and statuary. A small square pool stocked with goldfish and yellow water lilies also adorns the lawn. In 1927, French and his gardener, Charles Dupuy, replanted the garden in a revised palette of pastel perennials.
Chesterwood opened to the public in 1955. In 1962, French's nephew, landscape architect Prentiss French, designed a new circulation pattern to better accommodate visitors. Today Chesterwood is owned by the National Trust for Historic Preservation, which uses the grounds as exhibition space for contemporary sculpture as well as works by French. It was designated a National Historic Landmark in 1965.