The Corner of Hubbard Woods That Hasn't Changed Since 1980 Is Finally Up for Debate

Walk Green Bay Road on a First Friday evening and the Hubbard Woods Design District does what it always does. Gallery doors stay propped open past closing time. Someone is usually mid-brushstroke on a plein air canvas outside heARTstudio. A glass of something seasonal shows up in your hand without much effort on your part. It is the kind of low-key civic pleasure that makes a three-block stretch of storefronts feel like more than a place to run errands.

What most people sipping that cider on a Friday in October are not thinking about is that the specific buildings they are standing in front of are named, parcel by parcel, in a zoning application that would tear several of them down. That is not a hypothetical. It is sitting in front of Winnetka's Design Review Board right now, and it touches ground that has not seen a new building in almost half a century.

A Business District That Skipped Four Decades of Change

According to a brokerage report from SVN Chicago on the sale of the assemblage, the last major redevelopment in the Hubbard Woods business district happened in 1980, when McDonald's went in. Everything since then has been storefront turnover inside buildings that were already standing. The village eventually rebranded the corridor as the Hubbard Woods Design District and paid for streetscape work, but the bones of the block stayed the same.

That 46-year gap is the detail most residents walking past Doyle Opticians or Randoon's on a Friday evening have no reason to know. It also explains why the current proposal, filed under the name Tower Court Condominiums, reads less like a routine storefront swap and more like the first real test of what this district is allowed to become.

What Tower Court Condominiums Would Actually Replace

The project comes from OKW Architects, the same firm behind the separate One Winnetka development downtown, and it would assemble four parcels along Green Bay Road and Tower Court into one four-story building. The businesses on that footprint are specific: Rebel House interior design and Red Spade landscape design at 901-905 Green Bay Road, Bella Bleu Bridal and Alexandra Kaehler Design at 907-909, Munder-Skiles and a residence at 911-913, and Europa Motors at 1007-1011 Tower Road.

The version presented to the village in October 2025 called for roughly 15,400 square feet of ground-floor retail, 12 to 16 condominiums above it, and a height of 62 feet against Winnetka's 45-foot limit for that corridor, which meant the developer needed a zoning variance just to get in the door. Parking needed relief too. The village's own minimum for a project this size was 61 spaces, and the original plan came in under that.

By the time the project reached its second Design Review Board hearing in June 2026, the numbers had shifted. The revised plan calls for 14 condominiums, just under 16,000 square feet of commercial space, and 55 parking spaces split between nine at street level and 46 underground. The developer trimmed the unit count and reworked the parking math, but the height request has not gone away.

The Board Isn't Sold Yet

Katie Moor, who chairs the Design Review Board, called the revised version a "big improvement" over the first design but stopped short of an endorsement. As she put it during the June hearing, the project "doesn't feel like it fits" on that stretch of Green Bay Road, even accounting for the changes.

"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."

Trustees have split along similar lines since the project's first appearance before the Village Council. Tina Dalman told the board she loves the concept and expects it will be fantastic, though she flagged parking congestion as a real concern if the ground floor ends up with a restaurant. Kirk Albinson took the opposite position on the height variance specifically, saying he intends to hold the line on the corridor's 45-foot limit and worrying aloud that granting an exception here sets a precedent for the next developer who wants to build tall in Winnetka.

The project still has to clear Winnetka's Planned Development Commission before the Village Council makes a final call, and a third Design Review Board hearing was set for mid-July. As of the most recent public reporting, no final decision had been made. This is a process still in motion, not a settled outcome, and anyone who cares about that corner should expect more hearings before anything gets built.

What's Still Ordinary This Fall

None of that has slowed down the calendar. First Fridays in the Hubbard Woods Design District run monthly from May through October, and the season wraps up on October 2 with the Art Walk, the one night of the year built specifically around the district's galleries and working artists rather than general after-hours shopping.

A short list of what's actually on the books before the year turns:

• October 2 — First Friday closes its 2026 season with the Art Walk, featuring live painting demonstrations and gallery showcases along Green Bay Road between Tower Road and Scott Avenue
• October 23 — Hubbard Woods Park is set to become a pumpkin patch for the fall, per the Chicago's North Shore Convention & Visitors Bureau calendar
• Through November 20 — The Schmidt-Burnham Log House at 1140 Willow Road, the oldest log structure in Cook County, keeps its scheduled open afternoons under the Winnetka Historical Society before closing for the season

None of these require the zoning question to resolve first. They are the parts of Hubbard Woods that keep running on their own clock, regardless of what the Planned Development Commission decides next.

Why the Two Threads Are the Same Story

It would be easy to treat the First Friday calendar and the Tower Court hearings as unrelated items, one lifestyle news and one municipal news. They are not. The reason this particular assemblage matters is the same reason First Fridays work here in the first place: it is a small, walkable stretch of independently owned storefronts that has not been touched by large-scale redevelopment in 46 years. Whatever character residents show up for on a Friday evening exists because that gap in construction let it accumulate.

The debate in front of the Design Review Board is, at bottom, a debate about how much of that accumulated character survives contact with a modern four-story building. Trustees who love the concept and trustees who are steadfastly holding a line on height are arguing about the same tradeoff from opposite ends. Neither side has dismissed the other's point, which is itself a sign of how much is genuinely at stake on that corner.

Residents who show up for the Art Walk on October 2 will be standing in front of buildings whose future is still being decided a few blocks away at Village Hall. That is not a reason to skip the evening. It is a reason to pay attention to both calendars, the one with dates on it and the one with hearings on it, because Hubbard Woods in 2026 is being shaped by both at once.

If you are watching how this corner of Winnetka evolves, or thinking about what a home near a design district like this one is actually worth once its business mix starts to shift, Marcus Pesche Residential knows this stretch of the North Shore block by block. Contact us when you are ready to talk through what any of it means for you.