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Op-Ed Your Time August 27, 2025 · 5 Minute Read

What's Riding on the Post Office? The Future of Winnetka

The underused Post Office site is a once-in-a-generation chance for Winnetka to think big, execute, and shape its future.

What's Riding on the Post Office? The Future of Winnetka

How can the future of Winnetka hinge on a nondescript building site that's been underutilized for years?

After all, the village is still prosperous, friendly, beautiful, and a top location for people to live and raise families. On the surface, everything looks as idyllic as ever.

The challenges facing Winnetka, however, are not superficial. They run deep, and the post office site perfectly symbolizes the problem: an inability to execute long-term, BIG master planning without a crisis.

Most recently, it took the August 2008 floods to bring us all together to solve water conveyance and then we spent years exploring taking the stormwater under the tracks and dump into Lake Michigan?

One Winnetka finally has broken ground, but our decade-long private-public process meant our children only know boarded up storefronts in the East Winnetka Commercial Business District. We need to get better, think bigger, and execute.

The real question on the Post Office site isn't just what to do with that patch of land. It's existential: will Winnetka move forward -- thoughtfully, prudently, and confidently embrace a creative vision based on 21st century demographics and significant unmet residential and commercial unmet needs?

Winnetka in the Spin Cycle

This debate isn't new. More than 15 years ago, the village convened a blue-ribbon panel of architects, planners, and real estate experts. Local urban planner and landscape architect Scott Freres helped pitch a range of bold plans: a mix of community green space, retail, housing, and townhomes, all anchored by underground parking.

But the plan ran into resistance from a vocal minority, and momentum collapsed. Since then, the site—prime downtown real estate—has remained home to a squat 1950s-era building surrounded by asphalt. A wasted opportunity in the village's heart -- and a critical intersection in the West Elm business district.

Competing Visions

The debate is alive as ever. Some residents want a simple park, green space with minimal development. Others argue for a livelier mix -- restaurants, shops, housing, and better parking along with green space, which is what neighboring communities have done with their redevelopment opportunities at the center of town.

Freres reminds us that Winnetka was built by bold thinkers.

"Our forefathers made monumental changes," he said. "They put in a power plant on the lakefront to generate their own electricity. They drained marshy areas to build schools. They put the commuter train service underground. They had a plan - The Bennett Plan. Daniel Burnham said, 'Make no small plans.' What does Winnetka want to be in the next 75 years? This site should be a stake in the ground for that future."

He points to the Winnetka Music Festival as an example of the New Winnetka. "That took an extreme effort and bold creativity among a small group of individuals, led by Val Haller and Scott Myers, but it changed everything. It got a bit of the starch out of the town and was a community-building shot in the arm to everybody.

The Price Tag

There's also money at stake.

A park-only plan, Freres points out, could cost the village millions of dollars -- requiring physical maintenance and upkeep, as well as seasonal programming.

By contrast, a development that includes a mix of retail and housing would also require investment -- but would eventually bring revenue and, as a bonus, bring alternative housing choices to the village.

Charm vs. Change

Some see change as a threat to the village's character. Others see it as essential to keeping Winnetka vibrant.

"Look at comparable communities—Scarsdale, New York, Greenwich, Connecticut, and even nearby Wilmette," Freres said. "They've embraced housing, density, and downtown investment. We can't just freeze time. If we do, we risk losing the very vitality that makes Winnetka special."

A Rare Opportunity

For Ed Harney, who grew up in Winnetka and now is part of Our Town Winnetka, the post office site is a once-in-a-generation chance to solve long-standing unmet needs as well as making the West Elm Commercial Business District a destination. Winnetka gets to shape its destiny in ways many suburbs can't.

The village could embark on a public-private partnership, creating a model with a developer to deliver both public benefits—like green space—and private ones, like new housing and shops, he said, but that requires courage.

"I've lived all over the world. In great zip codes. And Winnetka has an opportunity to shape its destiny in ways many suburbs can't. We should be free of creating red tape for ourselves. We're not a big city. We are a home ruled community in charge of our own destiny. NOT A CITY.
"We've got incredible talent and intelligence here," Harney said. "What we need now is leadership—people willing to do the research, make tough decisions, and take the criticism that comes with them. That's what it takes to move forward."

What's Next?

The village council has scheduled a study session on September 9 to revisit the post office site. The agenda: weigh short- and long-term options and possibly set a timeline for action.

But talk alone won't do it. Here are four practical steps to finally move forward:

1. Set a firm decision deadline. Within six months of the next village council being sworn in, approximately this time next year. In fact, committing to a timely decision should be part of every candidate's platform during our upcoming WCC village council slating process and Fall Town Hall. 2. Master Plan the West Elm Business District. Leverage the 2024 Winnetka Plan to meet the needs of residents and commercial businesses. Yes, we can have open destination space, but let's use this opportunity to deliver: - Multi-family for families that want to stay and downsize; - Parking for our businesses to increase our tax base; and - A destination shopping district for local retailers to compete, if their customers can park.

As a side note, we have lost 3 car dealerships in 20 years -- that's a lot of commercial tax revenue. We need vision and big thinking beyond flower boxes, which are nice, but they don't directly generate revenue. 3. Conduct a nationwide search and hire a real estate consultant. We don't need a slew of new plans. We need an expert who can guide decision-making and shepherd the project to completion. 4. Host a series of public Town Hall listening sessions. Share the top three options with residents -- not for a binding vote, but to ensure the community is engaged and informed. Make them truly interactive, for those that can't attend or are traveling.

A Crossroads for Winnetka

Winnetka now faces a Robert Frost moment: It stands where two roads diverge. Staying still while other communities move forward is not an option—it only delays a choice that must be made.

The question remains: Which road will we take?

Published by Our Town Winnetka · Our Town. Our Future. Your Voice.  |  More Your Time →