Woodstock bans on-street parking between 2 a.m. and 6 a.m. for more than 30 minutes anywhere in the city. Most residents can work around that by requesting up to three overnight passes a month through the city's online system. People who live on the Square can't. The City of Woodstock's parking FAQ says so directly: the passes are open to "All City Residents (except those residing on the Square)."
For a buyer looking at a condo or a home above a storefront downtown, that one exception changes the showing. If the property has no garage or assigned space, the car spends the night in a public lot. The same FAQ says several lots near the Square allow parking for up to 24 hours. Winter tightens the rule. Once 3 inches or more of snow has fallen, parking is banned on streets and in public lots in the downtown business district after 11 p.m. A listing photo won't show that, and with this post going out in mid-November, it's about to apply.
One of Those Lots Is Now a Development Site
The city-owned parking lot at Jefferson and Calhoun streets, around 101 S. Jefferson, was once slated for a hotel. That plan fell through, and the City Council then approved a 180-day exclusive negotiating agreement with Zeller Multifamily Manager for a possible multifamily complex on the site, as the Northwest Herald reported. The city's Nov. 4 council packet dates that approval to Oct. 6 and describes the concept as a transit-oriented multifamily development of approximately 116 units.
That lot is where the parking question becomes concrete. Council member Melissa McMahon cast the only no vote. She told the council the city would lose more than 100 parking spots, "much of that is overnight parking for Square residents," and that she didn't want to approve an agreement without parking guardrails. Mayor Mike Turner backed the agreement but said the outcome wasn't decided. He said, "To not enter into discussion because we're worried about parking would simply be a mistake and would be bad, bad government and bad development."
Arlene Lynes, owner of Read Between the Lynes on the Square, told the council she fully supports development around the Square. "We understand we need that for our businesses to thrive," she said, and she added that parking needed to be a big part of the discussion so residents feel heard.
According to economic development director Jessica Erickson, the Jefferson and Calhoun site is what prompted a downtown parking study, which was scheduled to come before the City Council in November. Any deal on the lot also has to answer where the people who park there overnight now will go.
Three City Parcels, One Puzzle
The Jefferson Street lot is one of three city-owned pieces of downtown land in play right now. The other two are linked to it by parking, by location, or both.
| Site | What's planned | Where it stands |
|---|---|---|
| Former Die Cast property, next to the Woodstock Metra station | About 187 rental apartments in two phases, with an amenity center, open space and parking | Redevelopment agreement approved Aug. 18, 2026; formal design review and developer financing still ahead |
| City parking lot at Jefferson and Calhoun | A possible transit-oriented multifamily development of about 116 units by Zeller Multifamily Manager | 180-day exclusive negotiating agreement approved in October 2026 |
| 200 E. Judd St., a former lumber yard of about 1.13 acres | No final use; consultants have outlined parking options for it | Bought by the city for $350,000 in TIF funds |
The Northwest Herald's coverage of the Judd Street purchase shows how the pieces connect. Turner pointed out that the lumber yard site could connect to Jefferson Street, near the failed hotel site, and called it part of "a puzzle in a very strategic part of town." City building director Joe Napolitano said the parcel's zoning allows most businesses, offices and multifamily housing of up to 25 units without a special-use permit. Anything larger needs council approval.
So a parcel the city's consultants have studied for parking sits near a parking lot that may become housing.
Multifamily, Not Single-Family Homes
The Die Cast project has moved furthest. The city's Aug. 19 press release describes about 187 rental apartments built by MDG Woodstock LLC, an affiliate of Chicago-based Murphy Development Group. It puts the investment at more than $45 million. The plan was refined with Wight & Company, and the city's contribution includes the land, fee waivers and reimbursement from future property tax increment. Murphy still has to get through the city's formal development review and secure financing before the property is conveyed and construction can begin.
Zeller Multifamily Manager had competed for the Die Cast site with an apartment proposal before Murphy was chosen. Its Jefferson Street concept is described as multifamily housing, and the developer has asked the city to consider TIF assistance through a proposed TIF #4 district. Council member Tom Nierman said people have asked why Woodstock doesn't get something like the Enclave apartment development in Crystal Lake.
The Die Cast units are planned as rentals, and the Jefferson Street plan is a multifamily building. A buyer looking for a single-family home near the Square and the Metra station is still choosing among homes that already exist. Both projects would also bring more people downtown and more demand for the same limited parking.
Why the City Keeps Pursuing These Projects
The financing explains the city's persistence. On July 21, the council unanimously approved a new tax increment financing district covering the Die Cast site and nearby properties. The Northwest Herald explained that a TIF channels future property tax revenue from new development back into the district for 23 years. City Manager Roscoe Stelford said most of the property inside the district is city-owned, so its base value is $0. Any new development on the Die Cast site would be 100% captured by the TIF and used for the development's purposes.
Council members have also put the costs on the record. During the Judd Street vote, Council member Bob Seegers said the city already holds an inventory of undeveloped land and that TIF No. 2 is "in the red." Stelford said developers are more interested when the city owns the property and that he expects the TIF to succeed despite its current deficit. The purchase passed unanimously.
The city owns the land, has a financing tool tied to it, and a council majority favors more downtown residents. The open variable is parking, and that's the same constraint a car-owning buyer near the Square runs into.
What the For-Sale Numbers Say
Countywide data from Midwest Real Estate Data shows where condo and townhome buyers stand. In September 2026, the median sale price for attached homes in McHenry County was $280,000, down 1.8% from September 2025. Average market time was 37 days, and 114 attached homes were for sale at month's end. Detached homes ran differently that month: a $405,000 median, up 8.2% from a year earlier, with an average of 33 days on market.
These are county figures, not Woodstock-only figures. Still, they show the attached segment holding steady on price with a thin supply. The Die Cast apartments are planned as rentals and won't add to that for-sale supply. For condos and smaller homes near the Square, an assigned parking space or garage is one of the few features that sets one listing apart from another.
Questions to Settle Before an Offer Near the Square
- Where does the car go between 2 a.m. and 6 a.m.? If the answer is a public lot, confirm which one, and keep in mind that the Jefferson and Calhoun lot is the one under negotiation.
- Is the parking deeded, assigned or informal? An informal arrangement with a neighbor or landlord may not carry over to a new owner.
- What happens after a 3-inch snowfall? Downtown public lots close to parking after 11 p.m. once that threshold is reached.
- What's on the next council agenda? The parking study, the Zeller negotiation and the Die Cast design review all go through public meetings before anything is built.
The parking rules here come from the city's published FAQ and municipal ordinance. This post is general information, not legal advice, so confirm how they apply to a specific property with the city or your attorney.
FAQ
Is the Die Cast apartment project under construction? Not as of the city's August announcement. Murphy Development Group's plan still has to go through formal development review, and the developer must secure financing before the land is conveyed and construction begins.
Will the Jefferson and Calhoun lot definitely become housing? No. The council approved a 180-day exclusive negotiating agreement, and Mayor Turner said the outcome wasn't decided.
Can Square residents get overnight street parking passes? According to the city's FAQ, the up-to-three-nights-per-month passes are open to all city residents except those living on the Square.
If you own near the Square and are thinking about selling, the parking that comes with your home deserves a clear spot in your listing. Team Open Doors can walk you through how buyers are weighing parking downtown right now and how to present your home with that in mind. Get your free home valuation to start.
