The Noble–Seymour–Crippen House in Chicago's Norwood Park Historical Neighborhood looks from its current appearance to be only a few decades old with its modernist Italian-inspired design, but at least half of the house dates back to the early 1800's causing it to be considered by most to be the oldest house in the city, but there are those that call foul on the home's distinction.
The farmhouse that now comprises the basis for the current home's southern wing was built in 1833 by the same farmer who settled the area. When he purchased his land Chicago had not even been established yet, but was simply an ambitious urban expansion plan. Chicago finally incorporated the village of Norwood in 1893, bringing the farm into the city limits. Ownership of the house changed a number of times over the years, and the property was expanded upon but the original farmhouse that was the foundation of the residence was never torn down. Today the house has more than doubled in size and the historic farmhouse portion now seems to be the smaller portion.
This honor would be all well and good were it not for the Clarke House, a home built 1836 as part of the initial growth of the Chicago urban center. Supporters of this claimant to the title of Oldest House in Chicago argue that since the Noble–Seymour–Crippen House was not actually incorporated into the city until 1893, 56 years after the Clarke House which was part of the city from the beginning, it cannot be considered the oldest. Also it was a farm, while the Clarke House was always meant to be part of the city. So there.
The debate may never be settled but public opinion seems to side with the Noble–Seymour–Crippen House which now houses a museum and historical society which can be visited to discover more about Chicago's rich history. Just don't mention the Clarke House.
