The Doyle log cabin, built c. 1830 on Sheridan Road, pictured here c. 1880.
Building Winnetka’s Homes
For a village of less than four square miles, Winnetka has an impressive array of architectural styles. This is due to the preservation of homes built during a variety of time periods and the many talented architects that designed the village’s historic structures.
The first permanent homes were made out of materials found in the vicinity. Log cabins and houses were easy to construct and required little skill, making them the style of choice for early settlers.
The Log House is the oldest log structure in Cook County, built c. 1837, pictured here in 2021.
As the population grew and more settlers with wealth arrived, home building and design became more sophisticated and professionalized. Several Victorian homes, both grand and modest in design and size, popped up across the village in the latter half of the 19th century.
Click here to learn more about Winnetka’s architects and architecture.
592 Cherry Street, built 1896, pictured here in 2024.
At the turn of the 20th century, Winnetka’s built environment was forever changed with the construction of the first Tudor Revival homes. Since then, that style has become the village’s most pervasive. Designs by accomplished architects like William Otis, Spencer Solon Beman, and Mayo & Mayo contributed to the local popularity of the style, which persists to this day.
888 Tower Road, built 1909, pictured here in 2024.
If These Walls Could Talk
View the gallery below to learn about some “infamous” houses in the village.
The “Sham Mansion”
788 Walden Road was built in 1875 by corrupt developer E. Ashley Mears. Mears built 14 imposing Victorian mansions in the village, yet none were completed when they were sold. The Heinig family purchased and completed 788 Walden in 1885, and it is one of only two “sham mansions” that still stand as of 2024.