These houses on a hill south of the village center reflect Island Pond's two great industries—railroading and lumber. Facilitated by the railroad, the Fitzgerald Land and Lumber Company assembled more than forty thousand acres of Essex County forestland over the final quarter of the nineteenth century, processing culled wood in its steam-powered mills in Island Pond. For the design of their houses, the masters of this lumber empire, George and Henry Fitzgerald, followed the railroad to its Portland, Maine, terminus, where they commissioned the important firm of Stevens and Cobb. The architects published the resulting designs in their Examples of American Domestic Architecture (1889) to exemplify their concerns for moderation and straightforwardness in cottage design and the avoidance of “megalomaniac” extravagance.
George's house was the larger of the two. Despite his status as a “lumber king,” the architects regarded George instead as “a genuine American lumberman in the genuine American state of Vermont.” Thus, the house they designed for him is “unpretentious and comfortable.” A picturesque design that incorporates asymmetrical massing and roof slopes, it features gabled dormers, stocky chimneys, covered and uncovered piazzas with Tuscan columns, deep eaves with expressed rafter tails, an oriel window, and a polygonal conservatory. The variety is tamed by natural wood shingling, interlocking gables, and coordinated horizontals that draw it into a disciplined unity. Henry's compact shingled cottage is more tightly composed, dominated by interlocking gambrel roofs and a central chimney that recall the Fairbanks House in Dedham, Massachusetts, which architectural historian Vincent Scully invoked as an influence on Stevens in The Shingle Style and the Stick Style (1971). A long shed dormer assures the quiet horizontality of the roofline, seconded by a strong eave line, beneath which opens an asymmetrical inset porch with a single corner Tuscan column. Barring some replacement of windows and doors, the Fitzgerald houses remain remarkably true to the designs that Stevens and Cobb illustrated in their book.