[3] Naumkeag was designed by architect Stanford White of McKim, Mead & White in 1885 as the summer estate for Joseph Hodges Choate (1832–1917), a prominent New York City attorney and American ambassador to the United Kingdom from 1899 to 1905, and his wife Caroline Dutcher Sterling Choate, an artist and advocate for women's education.

[4] The house is built in the Shingle Style with a wood-shingled exterior featuring brick and stone towers, prominent gables and large porch, and interiors with fine woodwork.

Colonial settlement of the Prospect Hill section of Stockbridge began with the town's founding as a Native American mission community in the 1730s.

[5] The future site of Naumkeag was probably acquired by New York lawyer David Dudley Field in the 1870s, and purchased by Joseph Hodges Choate in 1884.

Choate persuaded Field (whom he had opposed in the Boss Tweed legal cases) to part with 40 acres (16 ha) on the south side of the hill.

[6] The house underwent a variety of alterations and additions, some guided by architects George de Gersdorff (Joe Choate's nephew) and Charles Platt.

[6] Joseph Choate first offered the landscape design to Frederick Law Olmsted, but rejected his proposal to place the house halfway down the hill, where a favorite oak tree was located.

[6] Choate commissioned White's friend and sculptor Frederick MacMonnies to produce a work; the result was Young Faun with Heron.