Walk Green Bay Road on any weekday evening this September and you will pass four storefronts that, depending on how a handful of Village of Winnetka meetings go over the next few months, might not be there in five years. Rebel House interior design. Red Spade landscape design. Bella Bleu Bridal. Alexandra Kaehler Design. Munder-Skiles. A residence tucked between them. Around the corner on Tower Road, Europa Motors. None of them look temporary. All of them sit inside the footprint of a proposed four-story building that Winnetka's own Design Review Board has now looked at three times and still has not signed off on.
That is the plain fact sitting underneath a fall calendar that otherwise looks exactly like Hubbard Woods always does in September: First Fridays, an Art Walk, a hot chocolate flight at the new place on the corner. The calendar isn't waiting on the vote. Neither is the block.
What the Design Board keeps sending back
The project goes by Tower Court Condominiums in the paperwork, and it would replace four parcels along Green Bay Road and Tower Court with a single building: one floor of retail, up to 14 condominiums above it, and a parking structure to match. The developer is the same team behind One Winnetka downtown, and the architect, Jon Talty of OKW Architects, is the same firm that designed that project too. This is not two unrelated stories happening in the same village. It's the same development company reshaping both ends of town in the same year.
The version reviewed in June proposed roughly 16,000 square feet of ground-floor commercial space and asked the Village for relief on two fronts that matter to anyone who has ever tried to park in Hubbard Woods on a Saturday. Winnetka's zoning calls for a minimum of 61 on-site spaces for a project this size, split between residential and commercial use. The current plan offers 55, nine of them at street level and the rest underground. The building's height has also required a variance from the start. Winnetka caps buildings in this district at 45 feet. The original 2025 proposal came in at 62.
The Design Review Board's chair, Katie Moor, called the revised version a "big improvement" over the first draft, then added the part that matters more: "This just to me, as it stands right now, still, even with the changes, which are terrific relative to version one, doesn't feel like it fits it." That was the board's second review, in June. A third hearing was set for July 16, and there's no public record yet of the board signing off. Even once it does, the project still has the Planned Development Commission and a final Village Council vote ahead of it before anyone breaks ground.
The design district, minus some of the design
Here is the detail that's easy to miss if you only read the zoning coverage: the businesses slated for demolition aren't a random assortment of retail. Rebel House does interiors. Red Spade does landscape design. Alexandra Kaehler Design does exactly what the name says. Munder-Skiles is a furniture house. These are, literally, design businesses, sitting on the same stretch of Green Bay Road that the Hubbard Woods Design District, a three-block corridor between Tower Road and Scott Avenue, uses to brand itself around art, home, design, and fashion.
That doesn't make the project wrong. A four-story building with condominiums and new retail is exactly the kind of density Winnetka has debated for years, and Trustee Tina Dalman said as much when the concept first came to the Village Council in October 2025, calling it something she thought would be fantastic. But it does mean the fight underway right now is not really about massing and setbacks, even though that's the language in the meeting minutes. It's about whether the block can add fourteen new households and a bigger retail footprint without losing the specific mix of small, design-focused tenants that gave the district its name in the first place. The board's discomfort with fit isn't abstract. It's this.
What's actually open while the board deliberates
None of that has slowed the block down. Hotel Chocolat, the British chocolatier, opened its Winnetka location at 912 Green Bay Road in April, taking over the space that Lana Jewelry vacated when its owner relocated the line to Oak Brook. It's the chocolatier's fifth Chicagoland location, and if you haven't had the drinking chocolate flight, that's reason enough to stop in before First Friday crowds make the counter three deep.
A few doors down, the food and drink options haven't gotten any less specific. Grateful Bites Pizza Shoppe, the wood-fired brick-and-mortar spin-off of Grateful Bites Catering, runs out of 899 Green Bay Road under family owners Matt and Sarah Halack, the kind of operation that doesn't chase national attention but anchors a block anyway. Towne & Oak, at 921 Green Bay, handles breakfast, lunch, and a fair amount of the neighborhood's private event catering without much fanfare. Neither business is new this year, but paired with Hotel Chocolat's arrival, they explain why Hubbard Woods evenings have gotten busier even while downtown, where One Winnetka is still rising at Elm and Lincoln, sits behind its own construction fence.
The calendar that doesn't check with the zoning board
First Friday in Hubbard Woods runs monthly from May through October, put on by the district's own merchants with after-hours shopping, live art demonstrations, and the kind of small-glass pours that make a Friday feel like an occasion without turning it into one. The September 11 date is the second-to-last of the season, and the district closes the year out on October 2 with Art Walk, its bigger, gallery-forward capstone event.
If you're planning around out-of-town guests this fall, that first-weekend-of-October date is the one to build a Saturday around. The event runs across the full length of the design district, and it's free to attend.
What this means if you already live here
The thesis of this fall in Hubbard Woods isn't that a big building is coming. It's that the neighborhood is negotiating, in real time and in public meetings you can attend, over how much of its own identity it's willing to trade for density. The Design Review Board isn't rejecting growth. It rejected a specific massing twice and is looking at a third version. The businesses in the crosshairs aren't struggling storefronts nobody will miss. They're the same category of business the district uses to describe itself.
None of that will show up on a for sale sign, and it shouldn't have to. But if you've lived in Hubbard Woods long enough to have an opinion on whether Green Bay Road needs fourteen new condominiums more than it needs Munder-Skiles, this fall is when that opinion actually has somewhere to go. Village Council meetings are open. The Design Review Board's process is public record. And in the meantime, First Friday still happens on the first Friday, whether or not the vote does.
If you're weighing a move within Winnetka, or wondering what a shift like this might mean for a home near Green Bay Road, The AVE Group knows this stretch of the North Shore block by block. Schedule a free consultation and we'll walk you through what's actually changing here, not just what's on the agenda.
