When my husband and I renewed our Chicago apartment lease for the fourth time, we promised each other it would be the last.
We’ve spent years preparing to buy our first home — protecting our credit, tracking mortgage rates, delaying travel, saving aggressively and endlessly scrolling listings late at night. We’re looking for what so many couples our age want: a two-bedroom condo with enough space to finally unpack the wedding gifts still sitting at my parents’ house.
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I work in real estate tech at Zillow. I expected the homebuying process to be expensive and time-consuming. What I didn’t expect was how hard it would be to see all our options.
I used to think home shopping worked like every other major purchase today — transparent, searchable and easy to compare. We can all research anything from flights and hotels to refrigerators and cars instantly from our phones.
But once we started seriously looking to buy in Chicago, I realized something crucial: Not everyone is shopping the same housing market.
Some buyers are seeing homes the rest of us don’t even know exist.
As my husband and I searched for our dream condo, I began noticing Chicago real estate agents I follow on Instagram advertising “exclusive listings” and “private inventory.” Curious, I’d look up those same neighborhoods on Zillow and a few other sites.
Nothing.
At first, I assumed it was just marketing language. But then I started seeing the pattern. Teasers of homes would appear in agents’ Instagram stories or in a post days, or sometimes weeks, before they showed up publicly — if they showed up at all.
I’d heard about private listing networks before, both through friends and through my job. But experiencing it firsthand felt different. It felt like browsing homes only after someone else had already gone through them first. We were just picking over what was left and unsure if we were seeing the real information about price reductions and days on market.
It changed how I think about the entire homebuying process.
I thought the internet solved transparency in shopping — I was wrong.
Now, the housing market feels to me like a store where some inventory is kept in a back room and whether you get access depends on who you came in with. Behind each door might be the right home, but they open only if we agree to work with the “right” agent or brokerage.
That’s what feels so backward.
The biggest financial decision my husband and I will ever make isn’t solely coming down to affordability or timing anymore. It’s becoming about access, and whether we’re able to see as close to the full picture as possible before we commit.
I thought the internet solved that already.
In almost every other part of modern life, we’re encouraged to research before making a purchase. If I’m buying a new kitchen appliance, or if my husband wants a new suitcase, we take the time to compare brands, read reviews and evaluate every option. That’s also been the case in real estate for the last two decades but not here in Chicago.
Homebuying, despite being a far more significant investment, increasingly feels like the opposite: commit to a salesperson first, then get access to inventory. Even then, you’ll only get to see the homes they choose to show you.
That doesn’t feel modern. It’s regressive and exclusionary.
My husband and I always planned to work with an agent — but we wanted to make that decision based on who we felt would work best for us as we navigate this major milestone. We thought that once we found homes online that we were serious about looking at in person and putting an offer on, we’d find the right agent to guide us from there.
But the reality is that we’re going to have to prioritize an agent’s access to listings over everything else, and hope we’re choosing the right person to unlock the right doors. The best homes could be getting sold before they ever reach the public market. What does that mean for us if we don’t give in to the “gatekeeping” of it all and play the game?
And the last few weeks have made that pressure feel all the more real. Thousands of listings in Chicago were taken down from Zillow when the regional listing service in my area, Midwest Real Estate Data (MRED), decided to cut off the information from Zillow in a play to protect private listings and serve those who benefit from the exclusivity agenda. As a buyer, it’s hard not to feel caught in the middle.
The homebuying system is fragmented and relationship-driven. After years of waiting, we’ve decided our next lease renewal really will be our last. By spring 2027, if we can’t find what we need ourselves through the same online resources nearly everyone uses, we’ll hire an agent and dive in.
But even then, I don’t know how when the time comes, we’ll feel confident putting in an offer if we’re not sure we have all the right information — which is tough to shake.
The internet transformed nearly every kind of shopping into something more transparent and accessible. Somehow, buying a home in Chicago feels like it’s moving in the opposite direction, toward a system where information is fragmented, access depends on who you know, and buyers are left wondering what they still can’t see.
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I expected homebuying to be hard. I work in this industry — I knew it wouldn’t be simple. What I didn’t anticipate was feeling like an outsider in a market I help build tools for every day. If I’m struggling to see the full picture, I keep thinking about the buyers who don’t have any of this context. What are they missing that they don’t even know to look for?
If I wasn’t prepared to navigate this with all the knowledge I have and access to the market disappearing overnight, how do we expect homebuyers to be?
Cam Lippert-Roof is a contract management specialist at Zillow. He resides in Chicago with his husband, their dog and cat. Cam holds a bachelor’s in advertising from University of Illinois Urbana Champaign.
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