Downtown Woodstock

Woodstock, Illinois Homes for Sale

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About Downtown Woodstock

Downtown Woodstock is a historic neighborhood dating back to the mid-19th century where residents enjoy the serenity of small-town Illinois paired with a wide array of highly accessible amenities. Built around the gorgeous park and brick streets of Woodstock Square, Downtown Woodstock offers a diverse business and entertainment district replete with shops, restaurants, and an opera house, not to mention a number of parks within the neighborhood itself. The overwhelmingly residential feel of the outer regions of the neighborhood further adds to the appeal of calling Downtown Woodstock home.

Quick Facts

Closed Prices: $105,000 to $331,500

Median Sale Price: $210,000

Association Fee Ranges: $134, $105 to $230/mo, $0

Type: Attached Home (Condo, Townhouse, Loft, etc.), Single-Family Home

Age: 1880 to 2006

Sq. Ft.: 725 to 2702 Sq. Ft.

Bedrooms: 1 to 5 Bedrooms

Bathrooms: 1 to 4 Bathrooms

Around Downtown Woodstock

Actor, director, and playwright Orson Welles spent much of his boyhood in Woodstock and reportedly performed in his first play at The Woodstock Opera House, which was originally built in 1889 to house City Hall, the library, the auditorium, and the Fire Department. Another legendary thespian, Paul Newman, performed with The Woodstock Players, who also call the Opera House home. Adding further to the bevy of celebrities who spent time in Downtown Woodstock, Dick Tracy creator Chester Gould lived in town for nearly half a century, drawing the popular comic from his Woodstock home. Downtown Woodstock was also home to the Emerson and Oliver Typewriter Companies, which were producing half of the world’s typewriters by 1922.

Downtown Woodstock is a relatively affordable neighborhood, with a median home price consistently below the Illinois median, as well as the national norm. While goods and services are perhaps slightly more expensive than comparable Illinois towns, Downtown Woodstock is overall an affordable place to live.

Located along Illinois state highway 14, Downtown Woodstock is approximately 70 miles from Chicago and around 40 from Rockford. Served by the Union Pacific Northwest Metra line and Pace Routes 807 and 808, Downtown Woodstock has transportation options to spare. While many residents rely on vehicular transportation to venture outside Woodstock, the downtown neighborhood itself is quite walkable.

Olson Elementary School, Dean Street Elementary School, Woodstock High School, and S.E.D.O.M. Center School are all located in the Downtown Woodstock neighborhood, while another four elementary schools, two middle schools, and Woodstock North High School comprise the Woodstock Public School System as a whole. Additionally, there are a number of pre-schools, private schools, and even a branch of Aurora University all within the city of Woodstock itself.

From art fairs and farmer’s markets in the summer months to the annual holiday parade and Christmas tree farms in the winter, Downtown Woodstock has something to offer the entire family. The Woodstock Opera House is one of the oldest continually operating theatres in the Midwest, the All Seasons Apple Orchard and Pumpkin Patch nearby is popular among residents, and the dozens of shops, stores and restaurants which line Woodstock Square are a great way to spend a weekend in lovely little Downtown Woodstock.

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