A lifelong resident of the Greater Gainesville area, Chessie Flanders offers her clients a rare combination of local market knowledge, financial expertise, and genuine personal care.

Chessie is a licensed REALTOR® and Broker Associate with REAL Broker, LLC, as well as Co-Team Lead of Synergy Group, an award-winning team of experienced real estate professionals dedicated to providing exceptional service to every buyer and seller. Before beginning her career in real estate, Chessie spent nearly 30 years in banking and finance, serving in leadership roles that included Vice President of Mortgage Lending, Vice President of Business Development, Commercial Lending, and Indirect Lending. She also developed and led successful teams throughout Alachua, Bradford, Union, Marion, and surrounding counties.

Her extensive background in lending, finance, negotiation, and business development gives her clients a distinct advantage when navigating today’s real estate market. Whether you are purchasing your first home, selling a longtime family property, relocating, investing, or building new construction, Chessie understands that every real estate decision is both financial and deeply personal. She takes the time to listen, explain each step clearly, and help her clients make informed decisions with confidence. A proud graduate of Santa Fe College and Saint Leo University, Chessie holds a bachelor’s degree in Business Administration with a specialization in Management.

She remains committed to continuing education and staying informed about the market, financing options, contracts, and industry changes that may affect her clients. Above all, Chessie has built her career around helping others achieve their goals and treating every client with honesty, patience, and respect. “Buying or selling a home is one of the most important financial decisions you may ever make. My goal is to stand beside you throughout the entire process, providing the knowledge, skill, communication, and personal service you deserve. I will work hard every day to earn your trust…and your business.”

—Chessie Flanders, Broker Associate