Oldfields is notable as a relatively intact, Midwestern estate of the American Country Place era (late 1800s-early 1900s), which was a time when the United States grew tremendously in population and economic strength. Some businessmen and industrialists profited handsomely, and many built expansive country estates where they could enjoy the beauty and tranquility of nature away from the noise, crowding and dirt of the cities. Popular magazines such as Country Life in America and House Beautiful promoted a genteel rural lifestyle to the middle and upper classes.

Wealthy European aristocrats and merchants had been building country estates for centuries, providing a range of design ideas for American architects and their clients. Although most American country houses were based on historical European styles, houses like Oldfields used modern building methods and materials, and included the most up-to-date conveniences.

American country estates of the early 1900s were often conceived with closely integrated architectural and landscape components, and with visually appealing transitions between the house, lawns and gardens. All major views, both interior and exterior, were carefully planned. At Oldfields, formal areas such as the Allée at the front of the house add grandeur and scale to the estate, while informal areas like the Ravine Garden and the Border Gardens invite quiet walks to view the changing displays of flowers.

The ideal country house lifestyle was one of rural recreation and genteel leisure. The country estate provided a splendid setting for recreational activities and pastimes such as equestrian sports, sailing, motoring, gardening and collecting.