Any good gentleman’s farm needs a superintendent to actually oversee all the labor being done to harvest crops and take care of the livestock (because a millionaire owner cannot be burdened to deal with such mundane matters…) When John Howard Whittemore, a successful industrial-era businessman purchased an old farm in Middlebury, Connecticut to spend summers and time out of industrial malaise, he knew that along with a summer home for his family, he would need to build other structures on the 300-acres of rolling hills. The famed architectural firm of McKim, Mead & White was hired by Whittemore to design many of the buildings on the grounds, from the main house, to the superintendent’s cottage to a boathouse. The firm designed this superintendent’s cottage (which currently looks to be getting a new roof) and the creamery in the rear. Both are great examples of the Shingle style in modest, agricultural structures.
Buildings of New England 
I see it rather as a modified Craftsman with, though hard to see, exposed rafter tails and a gabled dormer on the deeply sloping roof. I think Mckim, Mead and White gave this job to one of their junior partners who didn’t want too much “design” for the lower classes, ie. the bald “farmer’s porch” and the top-heavy dormer. Just saying.
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