After 14 years in the business, Matthew Neistat remembers walking construction sites and listening to his grandfather talk about deals ever since he was five years old. “My grandfather, my uncle and my father were all in real estate, so it felt natural,” he says. He has invested in land and apartment deals himself. “I don’t just sell real estate,” he declares. “I live it.”
Neistat learned Chicago by working it. His first six months were all rentals — every client, every price point. “It wasn’t just the grind, it was the listening,” he remembers. He learned by asking questions, remarking now, “The more I asked, the more I learned about people and what was important and what wasn’t.”
“I’d rather be honest and lose a deal than keep my mouth shut and close one,” he says. One client started as a deal that never came together, then became a friend; 10 years later, they did their first deal together. Neistat now advises him on his investment properties. He runs the numbers, and when they aren’t strong enough, he tells him to refinance instead of sell — no sale, no commission. He takes the same approach with other agents who call him for advice or referral business. “I don’t take their clients and send a referral fee; we work out a fair structure to do it together,” he says. “That’s the success — the trust, not the commission.”
A Chicago Association of REALTORS® Top Producer, Neistat received the 2025 Gold Residential Award in Jameson’s city hub office and is consistently listed among Jameson’s Quarterly Best. He recently won a Wicker Park duplex for buyers that went up against 24 competing offers — it was not just on price, but on due diligence, structure and terms. He represents buyers, sellers and commercial investors in Chicago, on the North Shore and in the northwestern and western suburbs, and consults for HOA boards and investors.
Outside of work, Neistat plays sports with his son and spends time with family and friends.
