Woodstock’s charming downtown is right out of central casting. The city’s historic turn-of-the-century town square, landmark Woodstock Opera House, and Old McHenry County Courthouse have a certain star quality.

It’s no wonder Woodstock made its way onto the big screen. The city was the hometown featured in the movie Groundhog Day and also appeared in Planes, Trains and Automobiles.

At one time Woodstock was known as the “typewriter city,” home to two major typewriter factories. Woodstock workers built more than half the world’s typewriters by the early 1920s. The factory eventually closed in 1970 and later converted to lofts.

Woodstock is a popular destination for live music featuring local, national, and international artists. The Woodstock City Band Concert is one of the longest-standing traditions with performances every summer dating back to 1885. The free Wednesday night concerts are held in Historic Woodstock Square and are often accompanied by an ice cream social. Woodstock also hosts a folk festival in July and Jazz on the Square Festival in August.

Commuters have direct access to downtown Chicago from the Woodstock Metra station along Union Pacific Northwest Line.

Woodstock map

Open Houses in Woodstock

Here are 6 Open Houses out of 170 listings in Woodstock

Featured Woodstock Listings

Here are 12 out of 170 listings in Woodstock


Union Pacific Northwest line at Woodstock Metra
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Data represents the community area's average over the past 12 months. All information deemed reliable, but not guaranteed.

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