Like its sister community of Brainerd to the north, Longwood Manor was established primarily by German and Irish immigrants whose families began to settle in the Midwest around 1880. Originally part of the larger neighborhood of Washington Heights, the area that is now called Longwood Manor was annexed along with Washington Heights into the city in the late 1800s.
The advent of the Rock Island Railroad, which still runs between Chicago’s far southwest side and the Loop, transformed the area just south of 95th Street into a bedroom community for immigrant workers. Many worked in the city by day and slept here by night. By the 1920s, development of the rail system prompted a population boom on the southwest side, which included the neighborhood of Longwood Manor. Overall, the area experienced a population increase of 80 percent, due largely to the influx of immigrants and the abundance of railroad jobs.
Longwood Manor was once home to a large number of oak tree groves that were scattered throughout the neighborhood. The tall, leafy trees provided a picturesque locale for a homestead, and it attracted many folks to settle down in the area. As immigrant workers moved in, they built durable homes that reflected the 1920s and ‘30s architectural style on the south side. Many of these homes are the stately brick bungalows that continue to give the neighborhood its classic, vintage charm to this day.
By the 1970s, many of the immigrant railroad workers who had built up Longwood Manor had lived out their lifespan. With the demographics of the south side changing as a whole and the majority of the original European settlers gone, many African-American families moved into the neighborhood. Today, Longwood Manor’s ties to its working-class history remain evident in its traditional architecture, however changes in the neighborhood’s makeup and commercial industries have welcomed it into the 21st century.