The Lawn on Chestnut Street Is Temporary. Here's What Winnetka Is Weighing for the Old Post Office Site.
November 5, 2026
November 5, 2026
"It's just unimaginative and boring and no trees," one resident told The Record North Shore at the first open house in June. She was talking about one option for 512 Chestnut St.: leave it as the grass it is now.
That option has since dropped out. Residents now favor a plan that keeps part of the lawn and adds a small building, and a majority of trustees agree. The open question is a smaller one with bigger consequences. Will the village pay to put parking underground? On the village's own preliminary numbers, that choice moves the project cost by about $9.9 million. It's also the strongest argument made so far for putting a larger building on the site.
The Record reports that the village has treated the post office parcel as a redevelopment opportunity for about 40 years. Almost all of the physical change has come since last fall.
The concepts covered a wide range. At one end the site stayed a lawn. At the other it became a full redevelopment, with a mixed-use retail and residential building over underground parking.
Participation was high for a downtown planning exercise. According to The Record's October report, 193 people came to the open houses and 679 answered the survey. Teska's Jodi Mariano said in June that the first open house drew "a very good turnout" compared with others she had run.
Concept 4 came out on top. Mariano called it a "partial redevelopment." It keeps part of the open space, adds a 1- to 1½-story commercial building that could hold a restaurant, and adds parking. Online participants ranked Concept 3 second. That plan expands the open space and puts parking underground.
The two favorites agree on most points: more green space than a full build-out and a low building, if any. The real difference between them is parking, and parking is the most expensive line in the analysis.
SB Friedman's preliminary cost analysis puts the project at $17.7 million with underground parking and $7.8 million without it. Burying the cars more than doubles the price.
Trustee Kim Handler wants that option kept open. "I think it would be very short-sighted to undertake this once-in-a-lifetime project and not put underground parking in place," she said at the session.
Once underground parking is on the table, the village has to find a way to pay for it, and that is where the hotel idea came from. Trustee Scott Myers proposed pursuing a boutique hotel on the site in place of a stand-alone restaurant. His argument turned on money and on activity. A hotel would be open to the public, could include a public restaurant, could program whatever green space remains, and "can provide additional tax revenue to help pay for underground parking."
He also warned that a lot of open lawn would put pressure on the village to keep scheduling events there to keep downtown busy. On that view, a large lawn isn't free once it's built. It needs ongoing programming.
Parking is already a live issue a block away. Our look at One Winnetka's fully leased ground floor found that the new corner at Elm and Lincoln leaves the parking strain with the village, and a decision at 512 Chestnut would affect the same downtown.
The positions at the October 13 session were more varied than a simple park-versus-building split. Each one, as The Record reported it:
| Speaker | Preferred direction | Stated reasoning |
|---|---|---|
| Trustee Bridget Orsic | Concept 4 | Keeps open and flexible space; restaurants have wanted to come to town but found no space |
| Trustee Kim Handler | Keep underground parking in play | Called skipping it short-sighted for a once-in-a-lifetime project |
| Trustee Tina Dalman | Seek development proposals for the whole parcel | Called Concept 4 "a real missed opportunity" and its building smaller than its neighbors |
| Trustee Scott Myers | Boutique hotel | Public restaurant, programming for green space, tax revenue for parking |
| Bob Horn, real estate developer | Boutique hotel | Said demand would be "extraordinary" and a hotel generates more tax base |
| Kitty Brandtner, owner of Little Elm, 847 Elm St. | Something besides open space, such as a hotel | Wants more foot traffic for downtown businesses |
Dalman explained her case as a long-term one. "I'm concerned if we go out for an RFP just on the open space that that limits us, because you're taking potentially what we may need in 40 or 50 years out of the discussion," she said. "My thought is, let's see what the market would present."
Brandtner, who runs a business on Elm Street, made the most specific case for a hotel. "Imagine a beautiful boutique hotel where grandparents can stay when visiting their grandchildren," she said. "As much as we all cherish the character of our old homes, we also know they don't necessarily accommodate long stays from parents and in-laws."
Supporters of Concept 4 argued for flexibility. One speaker said he and everyone he knew had chosen it, and he described its open area as a place food trucks could pull up in summer. "We bike to Kenilworth and Glencoe for the food trucks," he said. Another frequent speaker at village meetings compared Concept 4 to the 1921 Plan of Winnetka by Edward H. Bennett. "This is our last bastion in our village of public land," she said. "It belongs to all of us."
Both groups are making a claim about downtown foot traffic. One expects it from a building that brings people in, the other from a lawn people bike to. Underground parking makes the building more likely because it needs a revenue source, and makes the lawn more expensive to keep.
The October 13 direction leaves both paths open. Staff were told to issue a request for proposals or qualifications for open space and streetscape work. They were also told to send out a request for information to find out what developers might want to build on the north side of the site. Staff will work with the consultants on the RFI and interview developers to judge which use fits best.
In practice, the south side is being planned as public space now, while the north side waits to hear from the market. Whatever developers propose for the north side will show whether a restaurant, a hotel or something larger can carry the cost of parking underneath.
Village President Bob Dearborn has said the concept is preliminary and no final decision is close. "This is one step along the way," he said. "We're getting information. There are going to be decisions to make."
For now, 512 Chestnut St. is still the lawn trustees approved as a temporary step in October 2025. Its next form depends less on the sticker votes than on how the council answers the $17.7 million versus $7.8 million question.
What happens at 512 Chestnut will shape how downtown Winnetka works for years, from where people park to where visiting family stays. If you own nearby and want to talk through what these changes could mean for your property, Jena Radnay is glad to share what she is seeing. Request a Private Consultation.
Stay up to date on the latest real estate trends.
Jena Radnay, and the focus of her real estate business, is all about people. Radnay’s love for real estate, houses, marketing, and people have allowed her business to grow organically, albeit explosively, in large part from referrals from her extensive network of contacts and connections.
Let's Connect
