Rye House epitomizes American country house architecture from the late 19th and early 20th centuries. Although substantial in size and scale, such houses were in their day perceived as relatively informal, cozy, home-like retreats. For example, there are no grand staircases at Rye House, no ballroom, and only a modest dining room, appropriate for the family and a few visiting friends. There is a porte-cochere for arrivals, but only a small vestibule within, not the sort of place to accommodate guests by the dozens. Rye House's terrace, projecting rooms, and sun porches show the concern for fresh air, light, and relaxing vistas that was at the heart of country-house design. In terms of its style, Rye House is also representative of the period's country houses, many if not most of which were built in some variant of the Tudor or Elizabethan Revival styles. The rustic materials, late medieval details, and asymmetry of form implicit in the genre, all of which characteristics are well represented in Rye House, furthered the country-house program of "informal" living in picturesque surroundings. - US NRHP, 30 June 2000

Rye House has both architectural and historical significance. It is a well-preserved example of an early 20th-century American "country house," a type of residence characterized by large size and scale, landscaped grounds, and rich architectural detailing, generally in one of the period's "revival" styles (Criterion C). Rye House was designed by a nationally prominent architect, Wilson Eyre of Philadelphia, and epitomizes his particular approach to the country house in its arrangement of rooms, choice of ornamentation, and setting. Eyre entered sketches of the design in several architectural exhibitions and published them in American Architect in 1911. The house also documents an important development in the social history of Connecticut's western hills, the influx of wealthy New York City residents seeking weekend and seasonal homes in the region's rolling countryside (Criterion A). In Litchfield, Sharon, Kent, Cornwall, and other towns, these well-to-do urbanites typically bought large tracts of former farmland and forest and then erected what to them may have seemed modest country retreats but were, by the standards of the surrounding communities, mansions of impressive size and ornateness. The outsiders also added to the complexity of social life in the towns. Although they tended to socialize with their own social class (if at all), they also were neighbors, employers, taxpayers, and, in some cases, benefactors in their adopted communities. - US NRHP, 30 June 2000