Chicago Home Buyers Are Struggling… And It’s Getting Worse episode artwork

EPISODE · May 27, 2026 · 36 MIN

Chicago Home Buyers Are Struggling… And It’s Getting Worse

from People, Not Titles · host Stephen Kaempf

Chicago’s real estate market is going through one of the biggest shifts we’ve seen in years.Zillow vs Compass WAR Is Breaking Chicago Real EstateIn this episode of the People, Not Titles Podcast, Steve Kaempf and Matt Lombardi break down the growing battle between Zillow, Compass, private listings, and the future of real estate transparency in Chicago and across the country.From inventory shortages and rising home prices to Google’s re-entry into the home search market, this episode covers the real issues impacting buyers, sellers, investors, agents, and renters right now.00:00 – Chicago Real Estate Market Chaos Begins01:18 – Zillow vs Compass WAR Explained04:42 – Why Chicago Realtors Are Furious07:25 – Private Listings Controversy10:11 – Are Private Listings Hurting Sellers?13:08 – Dual Agency Problems Explained16:02 – Zillow’s $1.5 Billion Consumer Loss Claim18:45 – Chicago Affordable Housing Portal Update21:14 – New Rental Search System In Chicago23:26 – Massive Real Estate REIT Merger26:12 – Equity Residential & AvalonBay Deal28:44 – Google Re-Enters Real Estate31:05 – Google vs Zillow Future Predictions32:40 – Chicago Housing Market Statistics 202634:02 – Inventory Crisis & Rising Home Prices35:18 – Final Market Predictions & Closing Thoughts36:34 – EndChicago home prices continue to rise while inventory keeps shrinking, creating intense competition for buyers throughout the metro area. Steve and Matt discuss what this means for the future of the Chicago housing market and how investors and homeowners can stay ahead of the changes.This episode also dives into:→ Zillow’s legal battle with Compass→ Private listing networks→ Dual agency concerns→ Real estate transparency→ Chicago market trends→ Google is entering the housing search space→ Housing affordability challenges→ Real estate investment opportunitiesWhether you're a home buyer, seller, investor, realtor, or simply interested in the future of Chicago real estate, this episode delivers insider insights and real-world analysis you won’t hear anywhere else.Full episodes available at:www.peoplenottitles.comPeople, Not Titles podcast is hosted by Steve Kaempf and is dedicated to lifting up professionals in the real estate and business community. Our inspiration is to highlight success principles of our colleagues and provide market insights that help professionals thrive.Follow People, Not Titles:Instagram: https://www.instagram.com/peoplenottitlesFacebook:https://www.facebook.com/peoplenottitlesTwitter/X:https://twitter.com/sjkaempfSpotify:https://open.spotify.com/show/1uu5kTvSubscribe for weekly Chicago real estate news, market trends, housing insights, investment strategies, and business success conversations.#ChicagoRealEstate #HousingMarket #Zillow #Compass #RealEstatePodcast

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Chicago Home Buyers Are Struggling… And It’s Getting Worse

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