Jessie Oligschlaeger

Jessie is a proud Crawford County native, born and raised in Steelville, Missouri, where a deep appreciation for the land was instilled in her from an early age. Growing up, she spent her time riding horses, hunting, and helping work cattle, developing a lifelong passion for rural living and the outdoors. Coming from a family with over 50 years in the timber industry, Jessie brings extensive knowledge of timber, land management, and the unique value that rural properties offer. Before beginning her real estate career, she spent eight years working in banking and finance, building a strong foundation in customer service, financial transactions, and helping clients navigate important investments with confidence.

Today, Jessie enjoys spending time year-round on her family farm with her husband, Max, and their two boys. Whether she’s exploring the woods, working the farm, or enjoying the outdoors, her connection to the land continues to shape both her life and career. As a Land Specialist with Living the Dream, Jessie is passionate about helping clients achieve their goals. She understands that every piece of land tells a story, whether it’s a hunting property, productive farm, timber investment, or future homestead. Her local roots, firsthand experience, and commitment to exceptional service allow her to guide buyers and sellers with confidence every step of the way.