The kids are gone, the house in Winnetka has four bedrooms nobody sleeps in, and the plan is a condo on the Gold Coast. Walk to dinner. Lock the door and fly somewhere warm for February. Sounds simple.
Then we get to the garage.
A North Shore house usually comes with three bays, and those bays are full. A daily driver. Something fun for summer weekends. Maybe a project car under a cover that hasn't moved since 2019. Many Gold Coast and Streeterville towers sell parking separately from the unit, and some buildings have a waitlist just to get a space. I've watched deeded spots trade for what a decent sedan costs. In a few buildings, more.
So here's my opinion, and plenty of agents would push back on it. With downsizers, I don't start with the unit. I start with the parking. How many spaces, deeded or leased, tandem or side by side, and whether the building lets you store a car you won't drive all winter. If the garage answer is wrong, the view from the 40th floor won't save it. You'll resent the place by spring.
The emotional part shows up in the same spot. Downsizing is a hundred small goodbyes, and the garage is where people keep the things they can't decide about. The workbench. A kid's first bike. The car that was supposed to be sold years ago. When clients stall, it's rarely the price or the HOA. It's the stuff that won't fit in 2,200 square feet, and what it means to let it go.
I've spent 20 years running real estate teams in San Diego and Chicago, and the best agents I've trained all learned the same lesson: selling the big house and finding the condo are one conversation, not two. Plan the move out before you fall for the move in. Sell, store, or ship the extras on a timeline you set, not in a panic the week before closing.
A few things I ask every downsizing client:
- How many cars are you actually keeping? - What in this house are you sure you'll miss? - If the perfect unit had one space instead of two, would you still want it?
That last question tells me almost everything. Most people say yes after a pause. A few say absolutely not, and those are the clients I'm glad I asked first.
If you want to see what I'm seeing around Chicago and San Diego this fall, my Instagram is where it lands first.