Bold design amid a contemplative setting: Though established centuries ago, New Canaan, Connecticut, became a signpost of innovative architectural development after the so-called ‘Harvard Five’ began to use its gently rolling hills as the backdrop for some of the boldest design experiments of the post-war era. Consisting of Philip C. Johnson, Landis Gores, Eliot Noyes, and John M. Johansen, this informal group of architects, with the blessing and support of their wealthy clients, were able to push the boundaries within a variety of modern genres, crafting, as they did so, many of America’s most iconic homes. Today, their legacy lives on at both the sites they personally developed and nearby homes that, due to their impact on the city, were built according to a grander scope. Not every one of New Canaan’s homes reflects the philosophy of one of the schools of modern architecture, however, though even estates that were drawn along more traditional lines, including those inspired by the Federal/Adamesque, Cape Cod, Craftsman, and Georgian movements, have been built with the overall strength and history of the area’s housing stock in mind. Indeed, though noted for the superior nature of its properties, the city of New Canaan itself has many admirable attributes, including a highly educated, affluent populace, nationally-ranked schools, and convenient access, both by rail and highway, to New York City. New Canaan, after all, is also a favored residential area among New York’s elite as well as the many business people and scholars who call this sleepy part of Connecticut, which is within a short commute of many of America’s top academic institutions, home. Given its geographical position, high standards of living, and the intrinsic value of its exceptional architecture, New Canaan is likely to remain at the center of American culture for the next century and beyond.