With more than 30 years of experience in the real estate industry, Leigh Anne Chessher brings a wealth of knowledge, experience, and genuine care to every client she serves. Her real estate career began in commercial property management, where she managed more than one million square feet of retail space throughout Florida and Georgia. After marrying her husband, a residential building contractor, in 1993 and becoming involved in the family construction business, transitioning into residential real estate was a natural fit.

Born and raised in Florala, Alabama, just north of the Florida–Alabama state line, Leigh Anne has deep roots in the region and has spent decades living, working, and building relationships throughout Northwest Florida. Her extensive knowledge of the area, combined with more than three decades of real estate experience, gives her clients valuable insight into the communities and markets she serves.

Leigh Anne’s business has been built largely on repeat clients, referrals, and relationships developed over the years. She believes earning a client’s trust means working tirelessly on their behalf, communicating openly, and sometimes offering the candid advice they need to hear. Her combination of Southern charm, tenacity, and straightforward approach has become a hallmark of the way she does business.

Leigh Anne believes exceptional real estate service goes far beyond putting a sign in the yard or opening a door. She takes the time to listen, understand her clients’ goals, and guide them confidently through each step of the buying or selling process. Whether she’s helping a first-time buyer purchase their very first home, assisting a family with their next move, or helping longtime homeowners prepare to sell and begin a new chapter, she approaches every transaction with the same commitment and personal attention.

“My clients deserve someone who will advocate for them, communicate honestly, and be there when they have questions or concerns. My goal is to make the process as smooth and enjoyable as possible while helping them make decisions they can feel confident about.”

Continuing education has always been important to Leigh Anne, and she believes there is always something new to learn in an ever-changing real estate industry. She holds the GRI (Graduate, REALTOR® Institute), SRS (Seller Representative Specialist), MRP (Military Relocation Professional), and ABR® (Accredited Buyer’s Representative) designations.

Outside of real estate, faith and family are at the heart of Leigh Anne’s life. She and her husband have three adult daughters and three grandchildren, and she treasures every opportunity to spend time with them. She is active in her local church and enjoys giving back to her community. When she and her husband can get away, they love traveling and camping in their fifth-wheel RV. And when she’s home, you’ll often find her outside working in the yard or tending to a flower bed.

For Leigh Anne, real estate has never been simply about buying and selling houses—it’s about relationships, serving people well, and using decades of experience to help clients confidently navigate one of life’s biggest decisions.

When Experience Matters, call Leigh Anne.  

Leigh Anne Chessher, Realtor®

Email: leighanne@thepropertygroup850.com

Cell: (850) 685-3476