Chicago’s Real Estate Advisor — and Your Biggest Advocate.
Concierge Level House Hospitality™ | 15+ Years | Top 5% of Chicago Agents
A Country Boy Who Made It in the Big City.
My name is Olin. I’m not from Chicago — I’m a Southern boy who moved here over 20 years ago for a job at Harpo Studios and never left. I fell in love with the city, pivoted to real estate, and built a career from scratch. Now I’m in the top 5% of all Chicago agents, and I’ve crossed $150 million in career sales. But the number I’m most proud of? The clients who became lifelong friends.
Fun fact: When Olin is not selling homes, he is performing with The Beaus — a men’s vocal group touring the Midwest. Think big voices, great harmonies, and a whole lot of heart.
Visit The Beaus →You Are Safe Here.
The majority of Olin’s clients are part of the queer community — and that’s not by accident. It’s because word travels when someone truly sees you. As an out gay man who has lived and loved in Chicago for over 20 years, Olin understands what home means to our community. No assumptions, no awkward moments — just a realtor who gets it, fights for you, and celebrates every step of the journey with you.
“People feel safe and heard. That’s the whole point.”
Olin and his husband Andrew have called Chicago home together for years — living it out loud, building community, and proving every day that this city is a place where you can truly belong.
Olin & Andrew — Chicago locals, living it out loud.Chicago’s LGBTQ+ Heart — Two Neighborhoods You Need to Know.
Olin knows these streets like the back of his hand. Let him show you around.
Boystown (Northalsted)
The first officially recognized gay neighborhood in the United States. Vibrant nightlife, community events, Pride celebrations, and a strong sense of home.
Andersonville
A charming, walkable neighborhood on the North Side with deep LGBTQ+ roots, incredible local restaurants, boutique shops, and a warm tight-knit community.
Active Chicago Listings
Browse Olin’s current listings across Chicago’s most sought-after neighborhoods — from Boystown and Andersonville to Lakeview, Wicker Park, and the West Loop. Updated in real time on atProperties.
Find Your Chicago Home with Olin
Whether you’re a first-time buyer, relocating to Chicago, or ready to sell — Olin’s active listings are always up to date on atProperties Christie’s International Real Estate. Browse condos, single-family homes, and investment properties across the city’s best neighborhoods.
🔍 View All Active ListingsKnow the Best LGBTQ+-Friendly Vendors in Chicago?
From lenders and contractors to inspectors and movers — Olin has curated the ultimate resource list for Chicago home buyers and sellers. It’s yours, completely free.
No spam. Just resources. Olin’s word on it.
What Working With Chicago’s Best Realtor Actually Looks Like.
This is not a transaction. This is a relationship.
Chicago Neighborhood Tours
Olin personally picks you up and takes you through Chicago neighborhoods so you can feel the city, not just see it on a screen.
Face-to-Face First
Every client relationship starts with a real in-person conversation. Then the fun starts!
Custom Marketing Portfolios
Every seller receives a bespoke marketing portfolio — complete with Hermès zippers. Yes, really.
You’re Not Just a Client
Months and years after closing, you’re still invited. To events, to dinners, to life. Because keeping in touch matters.
Chicago Real Estate Myths — Busted.
Olin has heard every misconception in the book. Here’s the truth.
Not true. You can buy with 10%, 5%, even 3% down. Veterans can purchase with 0% down. The 20% rule just means you skip mortgage insurance — it’s not a requirement.
▶ Watch the reel hereThere are three strategies: price under to drive multiple offers, price above to test the market, or price at actual value. The right one depends on YOUR goals — not a blanket rule.
▶ Watch the reel hereRushing buyers into quick decisions actually backfires. List it right, show it properly, negotiate with intention. That’s how you win — not by cutting corners.
▶ Watch the reel hereYour Chicago Home Story Starts Here.
Whether you’re buying, selling, relocating to Chicago, or just curious — Olin is ready when you are. No pressure. Just real talk.
View All Chicago Listings →
Real Talk. Real Advice. Follow Along.
Olin keeps it honest — on camera, on the ground, and in your corner. Chicago real estate tips, neighborhood guides, and behind-the-scenes moments.