About Legacy Commercial Property
From left to right: McLain Hoogland, Sam Hoogland, Keith Hoogland, and Ben Hoogland.
Who We Are
A Family Legacy in Action
Legacy Commercial Property is a family-owned company built on decades of experience, entrepreneurial grit, and a deep belief in the potential of people and places. We come from a long line of do-ers, problem-solvers, and business owners who understand that success is also about helping others create their own legacy.
Guided by our Midwestern and Southern values and a multi-generational mindset, we approach every relationship by talking with the person in front of us and doing the hard work. We see opportunities where others see barriers and complexity. We meet people where they are.
Mission & Values
Growing with Purpose
Our mission is to use our creativity, grit, and personal touch to build America’s towns. We’re passionate about putting our best foot forward in everything we do, integrating our deeply held values in every interaction with our partners:
Our Story
Four Generations. One Mindset.
Legacy Commercial Property was born from the Hoogland family — four generations of Main Street entrepreneurs who kept reinventing the same core idea: find the right piece of ground, and everything else follows. Ours is a real estate story, but it didn't start out that way.
It starts in 1946 when our founder, Clarence Hoogland, opened a small appliance shop in central Illinois. When his son, Charlie, took over in 1953, he made a bet that would define the next four decades: he turned an overstock of movie inventory into Family Video, a chain that didn't just survive the industry's ups and downs — it outlasted nearly every competitor in the country.
What set Family Video apart wasn't just the movies. It was the real estate underneath them. Every store we opened, we owned outright rather than leased — and finding those sites took real creativity. We explored overlooked corners and secondary buildings other retailers had passed on and figured out how to turn them into some of the most visible, well-trafficked locations in their markets. By the time Keith Hoogland took the business into its third generation in 1995, growing it from about 40 locations to more than 800 nationwide, that instinct for site selection had quietly built one of the most valuable retail real estate portfolios in the country.
When streaming changed how people watched movies, we didn't see it as an ending — we leaned into what we'd already built: the real estate. That instinct, sharpened over three generations, is what became Legacy Commercial Property. Today, as part of our parent company, Highland Ventures, we continue to develop with the next generation in mind. Many of the same well-located corners we built a video business around are now home to some of the fastest-growing restaurant and retail brands in the country — proof that a great location outlasts any one business built on top of it.
Our Team
We’re a group of passionate, entrepreneurial-minded problem solvers dedicated to helping your business succeed. For more than 80 years we’ve been partnering with companies to support them from site selection to opening day.
Questions about Legacy Commercial Property?
Legacy has completed over 500 ground-up developments over the past 25 years. We’re a one-stop-shop for ground leases, cutting out the middle man by managing construction & property management in house. Our commercial real estate portfolio consistently grows each year. We buy our properties to hold.
