Bobby Simon
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Specialties
Since launching my real estate career in 2019, I’ve built a reputation for delivering results with integrity, precision, and relentless drive. I began by helping residential buyers and sellers navigate complex transactions, and over time, expanded my focus to include investor clients—ultimately transitioning into commercial real estate.
My passion lies in advocating for my clients and securing the best possible outcomes, especially when it comes to maximizing sale prices and structuring deals that align with their long-term goals. With over two decades of experience in the corporate world—working alongside everyone from C-suite executives to frontline technicians—I’ve honed a negotiation style that’s both strategic and empathetic. I understand how to read the room, manage expectations, and move conversations toward resolution.
Success hasn’t come easy, but my commitment to excellence and my refusal to settle have shaped every chapter of my career. I bring that same tenacity and client-first mindset to every commercial real estate transaction I handle, striving to deliver value, clarity, and results that exceed expectations.
Bobby Simon’s Transactions
$685,000
800 E Woodfield RD
Chicago
$387,000
- 4
- Bedrooms
- 3
- Bathrooms
- 2,116
- Square Feet
- 0.20
- Acres
$333,000
4823 W Irving Park RD
Chicago
$1,450
- 2
- Bedrooms
- 1
- Bathrooms
- 900
- Square Feet
