Woodstock · McHenry County · IL
Homes for sale in
Woodstock.
- Active listings
- 50
- Median list
- $470K
- Avg time on market
- 13 days
- Sold · last year
- 385
Photo: HrAtsuo / Wikimedia Commons (CC0 / Public Domain)
Active listings
50 homes on the market
About the community
Living in Woodstock.
Woodstock is the McHenry County seat, anchored by a National Register historic downtown Square with the 1889 Woodstock Opera House at its center. The Square doubled as Punxsutawney, Pennsylvania in the 1993 film Groundhog Day, Bill Murray filming sites are still plaqued around the district. Woodstock sits 51.6 miles northwest of Chicago and is the penultimate stop on the Metra UP-NW line (Harvard is the terminus). Home stock runs from 1880s Victorians on the streets near the Square through 1960s-2010s subdivisions on the city's edges. Woodstock CUSD 200 schools (Woodstock + Woodstock North HS) anchor family demand.
At a glance
~25,600 residents
McHenry County seat. 13.19 sq mi all land, density 1,944/sq mi.
Metra UP-NW
Woodstock station at 90 Church Street, 51.6 miles to Chicago Ogilvie. Fare Zone 4. 451 parking spaces.
Woodstock CUSD 200
12 schools serving ~6,123 students. TWO comprehensive high schools, Woodstock HS and Woodstock North HS.
Historic downtown Square
On the National Register since 1982. 1889 Opera House + 1857 Old Courthouse. Two-acre central public square anchors the district.
Groundhog Day filming site
1993 Bill Murray classic was shot here. Filming locations are plaqued around the Square, Public House, Tip Top Cafe, Ned's Corner.
Routes 14, 47, 120
US 14 bypass curves around the southwest; IL 47 runs north-south through town (currently being widened); IL 120 terminus at US 14.
County seat
Old + New McHenry County Courthouses both in Woodstock. The Old Courthouse hosted Eugene V. Debs's Pullman Strike sentence in 1895.
Home rule sales tax
Combined rate 8.50% effective Jan 1, 2026 (state 6.25% + county 0.25% + Woodstock home rule 1.25% + special 0.75%).
What’s close
Woodstock's life centers on the Square at the intersection of Main, Cass, Jackson, and Van Buren Streets. The Metra station is six blocks south. Residential neighborhoods radiate outward from the Square, with newer subdivisions on the city's edges along Routes 14 and 47.
- Woodstock Square Historic District
- On the National Register since 1982. Anchored by the Opera House, Old Courthouse, and Central Gazebo on the two-acre central public square.
- Woodstock Opera House
- 121 Van Buren Street. Built 1889. One of the oldest continuously operating theatres in the U.S., hosted Orson Welles, Paul Newman, Geraldine Page.
- Old McHenry County Courthouse
- Italianate 1857 building with distinctive white dome. National Register since 1974. Eugene V. Debs served his Pullman Strike sentence here in 1895.
- Woodstock Metra Station
- 90 Church Street. UP-NW penultimate stop, 51.6 miles to Chicago Ogilvie. 27 weekday trains, 20 Saturday, 15 Sunday.
- Schools
- Woodstock CUSD 200 covers the city K-12, Woodstock HS and Woodstock North HS plus six elementaries and two middle schools.
What it’s actually like to live here
Woodstock has a downtown that actually works, Main Street isn't a slogan, it's where people live their weekends. Read Between The Lynes bookstore, Public House (where Bill Murray drinks to world peace in Groundhog Day), Stage Left Cafe by the Opera House. The Woodstock Square Farmers Market on Tuesdays and Saturdays in the summer. The two-acre central square anchored by the 1889 Opera House and the 1857 Old Courthouse genuinely centers civic life here. That's rare for a McHenry County town and it's a real differentiator.
The Groundhog Day legacy still shapes Woodstock identity, annual Groundhog Days festival in February with a real groundhog (Woodstock Willie), a Bill-Murray-stepped-here plaque in the sidewalk, plaqued filming sites for a self-guided walking tour. The Orson Welles connection is the deeper cultural layer (Welles called Woodstock home in his memoirs). Schools (D200, with two high schools) hold family demand together. The Metra commute is real but long, about 95-100 minutes to Ogilvie, so most Woodstock buyers are people who actively want a downtown-anchored small city, not a quick-commute commuter address.
Neighborhoods
Detailed Woodstock community pages coming soon.
Browse the listings above. Detailed neighborhood pages with market stats, school info, and lifestyle take-downs land here as we roll them out.
Schools
Districts serving Woodstock.
Boundary lines do shift. Always confirm in writing for a specific address before writing an offer.
- D200Grades Pre-K – 12
Woodstock Community Unit School District 200
Schools serving the area
- Woodstock High School (501 W South St)
- Woodstock North High School (3000 Raffel Rd)
- Northwood Middle School
- Creekside Middle School
D200 covers all of Woodstock K-12 with two comprehensive high schools, two middle schools, and six elementary schools. Woodstock North HS opened per a 2006 referendum to address growth.
From the neighborhood
Around Woodstock
Real local creators on TikTok. Tap a tile to play it right here.
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@nicolefromchicagoAround town
What there is to do in Woodstock.
A handful of the places people who live here actually use. Not a directory.
- Culture
Woodstock Opera House
121 Van Buren Street. Built 1889. One of the oldest continuously operating theatres in the U.S. Live theatre, music, and the Orson Welles-dedicated stage.
- Culture
Old McHenry County Courthouse
Italianate 1857 building with distinctive white dome on the Square. National Register since 1974. Hosted Eugene V. Debs's 1895 Pullman Strike sentence.
- Food & Drink
Public House of Woodstock
Lower level of the 1857 landmark on the Square. The bar where Bill Murray and Andie MacDowell "Drink to World Peace" in Groundhog Day.
- Shopping
Read Between The Lynes
111 E Van Buren Street. Independent bookstore on the Square with an in-store café serving chocolates, ice cream, and coffee.
- Family
Groundhog Day filming sites walking tour
Self-guided walking tour of plaqued Groundhog Day locations around the Square. Bill-Murray-stepped-here plaque embedded in the sidewalk.
- Culture
Stage Left Cafe
Adjacent to the Woodstock Opera House and run by the City of Woodstock. Open mics, jazz, and storytelling nights.
Getting around
Commute + transit from Woodstock.
MetraUP-NW line
- Stations: Woodstock
- Terminal: Chicago Ogilvie (OTC)
- Distance: 52 miles to downtown Chicago
DriveBy car
- Routes: U.S. 14 · IL 47 · IL 120
- O'Hare Airport: ~74 min
- Chicago Loop: ~92 min
- Schaumburg: ~45 min
By the numbers
Woodstock taxes + market stats.
Property tax rates vary by exact township and assessor district. Confirm per address before pricing a purchase.
Property tax rate
2.67%
effective avg
Sales tax
8.50%
combined
Median sold price
$345,000
MRED · last 12 mo (385 sales)
Median household income
$83,293
ACS
How Woodstock got here
A bit of history.
Woodstock was founded in 1844 as Centerville, named for its location at the geographic center of McHenry County. It was chosen as the county seat on September 4, 1843, and early settler Alvin Judd developed the plat around a two-acre public square with a frame courthouse and jail. In 1845, resident Joel Johnson proposed renaming the town after his hometown of Woodstock, Vermont. The village was incorporated in 1852 with Judd as president and gained city status in 1873. By 1922, Woodstock factories had built more than half the world's typewriters at the Emerson Typewriter Company and Oliver Typewriter Company, earning the city the nickname "Typewriter City."
The Woodstock Square Historic District was added to the National Register of Historic Places on November 12, 1982. Inside it sit the Woodstock Opera House (1889) and the Old McHenry County Courthouse (1857), both individually listed on the National Register since 1974. Orson Welles attended the Todd School for Boys in Woodstock from 1926 to 1931, his only formal education, and later returned in July 1934 for the Todd Theatre Festival at the Opera House, where the stage is now dedicated to him. The 1993 filming of Groundhog Day made Woodstock Square globally recognizable; principal photography ran March 16 to June 10, 1992, with the Square standing in for fictional Punxsutawney.
The questions buyers actually ask
Woodstock FAQ
The questions I get most from buyers shopping Woodstock. If yours isn't here, text 224-385-8779, same-day reply.
- Is Woodstock the Groundhog Day town?
- Yes. The 1993 Bill Murray film was shot here on the Woodstock Square in spring 1992; the Square doubled as fictional Punxsutawney, Pennsylvania. Filming sites are plaqued around the Square, Public House (where Bill drinks to world peace), Tip Top Cafe (now under different names), Ned's Corner. The annual Groundhog Days festival in February features a real groundhog named Woodstock Willie. Bill-Murray-stepped-here plaques are embedded in the sidewalks.
- What's the Metra commute really like from Woodstock?
- Woodstock is 51.6 miles from Ogilvie on the UP-NW line, the penultimate stop (Harvard is the terminus, with some trains short-turning at Woodstock). Inbound commute time runs roughly 95-100 minutes depending on the express schedule. 27 weekday trains, 20 on Saturday, 15 on Sunday. Most Woodstock buyers are people who actively want the small-city downtown experience, not folks chasing a quick commute. If your job is in the Loop and you want sub-75 minute Metra, look at Cary or Crystal Lake instead.
- How are Woodstock schools?
- Woodstock Community Unit School District 200 covers all of Woodstock K-12, 12 schools serving ~6,123 students. TWO comprehensive high schools: Woodstock HS and Woodstock North HS (the latter built per a 2006 referendum to address growth). Six elementaries, two middle schools, plus the Verda Dierzen Early Learning Center. Boundary lookups are at woodstockschools.org.
- What are property taxes like in Woodstock?
- Woodstock had the highest 2022 effective property tax rate (~2.67%) among selected northeast Illinois municipalities, per the Civic Federation. The city's own portion is under 16% of the total bill, and the City Council has declined PTELL increases for 10 consecutive years, so the rate is driven by school districts, the county, and other taxing bodies, not by Woodstock's own levy. On a $300,000 home that's roughly $8,000/year.
- Is the downtown Square actually a real downtown?
- Yes. The Woodstock Square Historic District is on the National Register and centers on a two-acre public square with the 1889 Opera House, 1857 Old Courthouse, and Central Gazebo. People actually walk it, to the Opera House for shows, to Read Between The Lynes bookstore, to Public House for dinner, to Stage Left Cafe for open mics, to the farmers market on Tuesdays and Saturdays in summer. That's rare for a McHenry County town. If you're coming from the city and worried about suburban strip-mall sprawl, Woodstock is the suburb that doesn't feel like that.
- Where should I look first in Woodstock?
- Depends on what you're optimizing for. Walkable to the Square, with character: 1880s-1920s Victorians and bungalows on the streets immediately north and west of downtown. Established mid-century: 1950s-70s ranches and splits on the city's south and east sides. Newer family subdivisions: 1990s-2010s product along Route 47 and Route 14 on the city's edges. Tell a Subdiview agent what matters most and they can match you to two or three neighborhoods worth touring.
- Anything to know about the Route 47 widening project?
- Yes. IL Route 47 through Woodstock is being widened by IDOT (2026-2028) to two lanes each direction with roundabouts at major intersections. The project will improve north-south through-traffic flow but means construction zones on Route 47 through downtown for the next ~2 years. If you're touring homes near Route 47, factor in current construction conditions plus the eventual improved access.
Nearby
Towns next to Woodstock.
If you’re cross-shopping the area, these are the places that border Woodstock.
Your local agent
Joe knows Woodstock
Most agents will list anything. I focus on the places I actually know, and the things that move value here don't show up in the MLS write-up: which streets and buildings hold demand, what the HOA or assessments really cover, how the comps read once you account for condition and location, and where buyers consistently want to be.
When you're ready to tour or list, you want someone who has read the last 50 closed comps in this specific market, not a national average, and can tell you what they actually mean for your price. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Licensed Illinois broker
- Comp-driven pricing
- Woodstock specialist
- Honest local market take
- Brokerocity
Thinking of selling?
What's your home actually worth?
Not a Zestimate. A real CMA from someone who's sold this neighborhood, knows the floor plan premiums, and can tell you which upgrades the buyer pool here actually pays for.
- Pricing range with comp-by-comp logic
- Pre-list improvements that pay back, and the ones that don't
- No obligation, no spam, no auto-dialer