Jason bought his first farm over 30 years ago and has bought and sold many since. His primary focus is helping his clients through the process whether they are buying or selling a property. Through many years of managing his own farms, Jason understands the full potential of the land. He has experience in lake construction, harvesting timber, new building construction, native grasses, and tillable food plots.

Jason is a full time Missouri real estate broker who is passionate about helping his clients make the most educated decisions when buying or selling.


Jason Cleveland is a graduate of Southeast Missouri State University with a B.S. in Agriculture and has extensive experience in private land management throughout the Midwest.

After a successful career in the pharmaceutical industry Jason received his real estate license in 2007.

Jason earned his Brokers license in 2012 and co-founded Trophy Properties and Auction along with business partner Phil Brown. Together, they have built one of the fastest growing brokerages in the Midwest.


Jason taught Midwest Fly Fishing School for Orvis and was the head guide at an Orvis endorsed lodge in Utah for pheasant hunting and fly-fishing. In addition, he has guided hunts for trophy whitetails, turkey, and ducks while being a hunting TV show personality. Jason is active in his community and currently serves on the Board of Directors for Great Rivers Habitat Alliance and is a Life sponsor of Ducks Unlimited.

Jason has been married to his wife Jeanne since 1996. They have two beautiful daughters and they love spending time outdoors hunting and fishing. They adopted the moniker #Feedthefamily and live the lifestyle year round at their home and their farm.


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What a pleasure it was working with Jason Cleveland of Trophy Properties. I had the opportunity to work with Jason on two occasions and if I ever need to sell a home or a farm in the future I will be delighted to call Jason Cleveland of Trophy Properties. Not only did Jason do a great job, but I also feel like I made a great friend.

Bill Jennings, St. Louis, MO

After being in the market for a farm for a while, and unsuccessfully working with other agents, Jason Cleveland took a personal approach to my search. He is very knowledgeable about land management and his team has a very broad network of resources that other agents don’t have. If you are in the market for a farm, hunting property, or weekend getaway, you will not find a better agent.

Tom Henneberry, St. Louis, MO

Jason assisted us when we were looking for recreational land near St. Louis. He was such an easy going, smart, trustworthy, and charming person. He is super patient and easy to discuss any matter frankly with. We are extremely happy with the land and the transaction. We highly recommend him

Chris & Liz Solaro, Quincy, IL

Jason Cleveland exceeded my expectations. From day one he impressed me with his work ethic and broad knowledge of hunting and farmland. Jason knew what I was looking for and came to me with the perfect property. I appreciate the drive and enthusiasm and would definitely work with him again.

Ron Janes, Chesterfield, MO