Tampa, FL, April 23rd, 2026–Written by Austin McWilliams
I’m so humbled to be writing my first Eshenbaugh Report article here, although this one is a bit more personal than what will be my frequent updates to you all on the general Orlando market.
I was born at Overlook Hospital in Summit, New Jersey. Ironically, so was Ryan Sampson — just a few years before me. Apparently Overlook Hospital has a type that Eshenbaugh likes.
At age nine, my father traded the long hours of Investment Banking in New York for something with more work/life balance in Central Florida. He landed in commercial real estate investment and advisory at CNL in downtown Orlando. I grew up watching that world from the dinner table, and thirty-some years later, I’m still here — a second-generation CRE professional who never really left.
I graduated from Trinity Preparatory School, where I competed in competitive Public Speaking events and was a State Champion — a skill that, it turns out, translates remarkably well to negotiating land deals. I went on to Wake Forest University to study Mathematical Economics and later earned my MBA in Finance and Management from the Crummer Graduate School of Business at Rollins College.
I didn’t come straight to real estate like so many of my peers. After Wake Forest, I spent meaningful years in teaching, youth ministry, and the nonprofit world. Those years shaped how I think about relationships, communication, and why any of this work actually matters. It’s not the typical path for someone who now spends his days structuring land transactions across Central Florida — but these experiences helped shape who I am and my values.
I entered brokerage in 2017 at a boutique shop, bird-dogging deals for a car wash developer. One site led to another. Car washes gave way to larger tracts, and over the last several years I’ve completed dozens of transactions across the region — single outparcels to large-scale master-planned developments — with a focus on multifamily land over the last five years. In 2024, that work earned me a CoStar Power Broker Award, which I’m proud of, though I’ll admit my three kids under five were more impressed with the little plaque than the credential.
Outside of work, I serve on the boards of Pinnacle Counseling Institute, Central Florida’s Apartment Life Advisory Board, and the Trinity Prep Alumni Association, and currently serve as Vice President of the French Quarter HOA. My family and I are active members of Orangewood Presbyterian Church.
When I’m not sourcing sites or navigating a land assemblage, I’m home in College Park with my wife Holly, our three children, and two small dogs — a full house by any measure.
What excites me most about what we’re building in Orlando is the makeup of our team — former developers who understand land from the inside out, paired with people who are genuinely wired to serve. That combination is rare, and I think the market will feel the difference. I look forward to introducing you to the people behind it.
Interested in selling or learning more about the Orlando land market? Feel free to contact me at 407-619-6435 or austin@thedirtdog.com.