Confession time. I Zillow people. 🙋♀️
Someone mentions they bought a house in Aspen? I’m hunched over my keyboard like a Nancy Drew reboot. New potential deal on deck? I’m looking at where the guy or gal lives and how much of a mortgage they have on the house.
I know I’m not alone. Zillow pulled 221 million average monthly unique users in Q4 2025, up 8% year over year. We’re all doing it.
Here’s what changed. AI has made Zillow stalking significantly more powerful.
🔍 What Zillow already gives you
Type any address into Zillow, and you get the Zestimate, their AI-calculated home value estimate built from public records, recent sales and tax data. Accurate within 2% for homes on the market. Within 7% for off-market homes.
You also get price history, what the buyers paid and when, estimated rent, tax assessments and square footage. It’s a financial X-ray.
Nobody can hide it. Zillow doesn’t let homeowners delete or suppress their sale history. That coworker who’s been vague about their upgrade? Fully searchable. You’re welcome.
🤖 This is wild
Typing an address into Zillow is the old way. A pair of AI prompts is the 2026 way.
Open ChatGPT, Claude, Gemini or Grok and start with this:
“Someone I know lives at [address]. Based on public records, what can you tell me about this person’s financial picture? What did they likely pay, what do they probably owe and what does this home say about their income bracket and financial priorities?”
That’s the baseline read on someone. Now run this second one:
“Based on the neighborhood, purchase price and home size at [address], what kind of lifestyle does this suggest? What would I likely find out about this person’s financial situation that they probably don’t advertise?”
That second prompt is the one that makes you feel like you work for the FBI. AI is remarkably good at connecting dots you didn’t know existed.
I tested this on someone I was about to do a deal with. The second prompt told me they’d bought at the peak of the market in 2024, were likely underwater and had refinanced twice. None of that came up in our conversation. All of it changed how I negotiated.
📩 Send this to someone who met a new business contact, has a neighbor they’ve been dying to look up or simply can’t stop hitting refresh on Zillow at midnight. You know exactly who.