Caleb Jessup | Seattle and Eastside Real Estate Agent
Caleb is a trusted Seattle and Eastside real estate agent with lifelong roots in the Greater Seattle area. Born in Kirkland and raised in Bothell, he brings unmatched local insight into the neighborhoods, schools, and lifestyle opportunities across the Eastside and surrounding Seattle suburbs. As an Inglemoor High School alum, Caleb’s connection to the community is deeply personal—this is not just where he works, but where he has built his life. Caleb earned his Communications degree from Western Washington University, where he was also an All-American student-athlete. His background in competitive athletics instilled discipline, focus, and a results-driven mindset that continues to shape his approach to real estate today.
A Data-Driven, Modern Approach to Greater Seattle Real Estate
Before transitioning full-time into real estate, Caleb worked in the tech industry, helping build and scale one of the fastest-growing marketing startups in the Pacific Northwest. This experience gives him a distinct advantage as a Seattle-area Real Estate Agent—leveraging advanced digital marketing strategies, data analysis, and negotiation expertise to help clients win in a highly competitive market. Caleb specializes in residential real estate across Kirkland, Bothell, Bellevue, Woodinville, Brier, and Greater Seattle. His marketing strategies are designed to maximize exposure, generate strong buyer demand, and achieve top market value for sellers, while his strategic guidance helps buyers make confident, informed decisions.
Trusted Eastside REALTOR® Focused on Results, Strategy & Relationships
With extensive knowledge of Seattle and Eastside real estate trends, pricing strategies, and long-term investment potential, Caleb provides more than transactional support—he offers strategic real estate guidance. Clients appreciate his integrity, responsiveness, and ability to simplify complex market conditions. Whether assisting first-time homebuyers, luxury sellers, or clients focused on long-term wealth building through real estate, Caleb is committed to delivering a professional, transparent, and high-touch experience from start to finish.
Windermere Real Estate | Northeast Office
Caleb is proud to be a Windermere Real Estate agent, representing a brand known for integrity, market leadership, and community involvement. He plays an active role at the Windermere Northeast office—one of the top-producing real estate offices in the Greater Seattle and Eastside markets—giving his clients access to exceptional resources, market intelligence, and a powerful professional network.
Life Beyond Real Estate
Caleb lives on the north end of Lake Washington with his wife, Jennifer, and their four children.
