I’m a Chicago-based real estate agent and active investor who helps buyers and investors build real wealth through smart, data-driven real estate decisions. From first-time house hackers to seasoned multi-unit owners, I bring firsthand investing experience to every deal.

I didn’t start in real estate as an agent — I started as an owner and investor. My journey includes purchasing condos, building a multi-unit rental portfolio, running short-term rentals, and scaling long-term buy-and-hold properties in both Illinois and the Midwest. That experience gives my clients something most agents can’t: real-world insight into cash flow, ROI, financing strategy, and long-term wealth building.

Today, I lead the Josh Reighard Group and specialize in helping:
• House hackers and first-time investors
• Multi-unit and mixed-use buyers
• Out-of-state and remote investors
• BRRRR and value-add investors
• Short-term and long-term rental owners
• Traditional buyers and sellers

Whether you’re analyzing a 2-flat in Pilsen, a mixed-use in Bucktown, or an off-market opportunity, I approach every deal like it’s my own money on the line. I focus on cap rates, expenses, tax advantages, financing structure, and exit strategy — not just “getting a deal done.”
My background also includes deep experience with advanced real estate tax strategies, including cost segregation, S-corp structures, and investor-focused planning, helping clients maximize returns and protect cash flow.
Clients work with me because I’m:
✔ Highly responsive
✔ Straightforward and honest
✔ Numbers-focused
✔ Long-term relationship driven
✔ Invested in their success beyond one transaction

If you’re looking for an agent who understands both sides of the table — investor and advisor — I’d love to help you build your portfolio the right way.
Let’s connect and talk strategy.