Leigh Ann Chessher

Leigh Ann Chessher

  •   5   (14 reviews)

About Leigh Ann

With over 30 years of experience, Leigh Anne began her real estate career as a Commercial Property Manager, managing over 1,000,000 square feet of retail space in Florida and Georgia. After marrying her husband, who is a residential building contractor, in 1993, and assisting him in his construction business, listing and selling residential real estate was a natural transition. Leigh Anne’s success is based almost exclusively on positive referrals. She earns the respect of her clients by working tirelessly on their behalf and by always offering candid advice. Reared in the local area, she has an effective combination of Southern charm and tenacity. “I listen to my clients’ wants and needs to achieve the best outcome in every transaction, and I strive to ensure that the home buying or selling process is fun, easy and stress-free. My clients can count on me anytime of day when they have a question or concern.” Leigh Anne enjoys time spent with family. She has three adult children who were educated in the Okaloosa County School system and three grandchildren. In the summer, her grands enjoy “Tuesdays with Granna.” She’s active in her local church, and she and her husband enjoy time away at their retreat at Lake Eufaula, Alabama. When time allows, you’ll find her weeding a flower bed or two and working in her yard. ​

Leigh Ann's reviews

  5  
Leigh Ann has 14 reviewsacross 5 different locations, showing 6.
Review Leigh Ann
9 months ago
Leigh Ann is absolutely the best!

Leigh Ann Chessher recently helped us with the purchase of a new home. We had also received her help in the past with a property sale. She has been consistently professional, knowledgeable, and invaluable with her assistance. She helped us avoid mistakes in every process, saving us money and grief. We will continue to rely on Leigh Ann for any real estate transaction in the future. We are so happy with our new home purchase. We highly recommend Leigh Ann and Property Group 850.

9 months ago
One of the best in Real Estate

Selling a home can be stressful, but working with Leigh Anne Chessher turned it into a smooth and confident experience. She came in with a strong strategy, positioned our home perfectly, and had us under contract in 16 days, even better, we closed in 30 days. Her attention to every detail made all the difference. She knew exactly how to market our home. If you are selling and want someone who delivers results, with a personal touch, Leigh Anne Chessher is one of the best in the business!

11 months ago
Realtor Review

We recently had the pleasure of working with Leigh Anne Chessher, Realtor, to buy our home, and we couldn’t be happier with the experience. From start to finish, Leigh Anne demonstrated an exceptional understanding that of the local market and a keen ability to spot properties that perfectly matched our preferences. Her attention to detail, warm personality, and unwavering dedication made the entire process smooth and enjoyable. We are beyond grateful for her expertise and would highly recommend her to anyone looking to buy or sell a home.

12 months ago
I highly recommend Leigh Anne

I have bought and sold many homes over the years, but I never worked with a better realtor than Leigh Anne. She is professional and personable at the same time. Her experience, knowledge, honesty, and insight separate her from her peers. I can’t recommend her enough. Thank you Leigh Anne!

about 1 year ago
Amazing Realtor!

Leigh Ann is the best. She’s helped my family purchase and sell a home. She makes sure to always communicate everything that is going on and we never felt like we had any questions. Leigh Ann goes above and beyond. I would recommend her for any of your real estate needs!

about 1 year ago
Expert service and performance!

Leigh Anne’s expertise, knowledge, and dedication has placed her at the top of her peers, and she has come through for our family yet again. During a transitional market, Leigh Anne worked 3 family properties under contract in single-digit days. Two properties in 7 days, and our most recent sale in 9 days on the market! She has a true gift for staging and marketing, and is able to attract high quality buyer’s agents with phenomenal clients. Leigh Anne has worked 4 transactions for us in the past 7 months, making our big life changes so smooth and easy. She is the only agent we call due to her outstanding effort, performance, and service for our family.

Show all 14 reviews

Leigh Ann's properties

Leigh Ann has 4 properties for sale and sold 10 properties in the last 12 months, showing 4, sorted by most recent activity

Pending
$175,000
355 West 1st Avenue
Crestview FL 32536
3
2
Single-Family
Listing courtesy of The Property Group 850 Inc
Pending
$250,000
501 Jones Road
Crestview FL 32536
3
2
2
Single-Family
Listing courtesy of The Property Group 850 Inc
SoldMar 20, 2026
$340,000
2837 Tamiami Trail
Crestview FL 32539
5
2
2
Single-Family
Listing courtesy of Coldwell Banker Realty and The Property Group 850 Inc
SoldMar 19, 2026
$318,133
Homesite 6I/6361 William Kidd Drive
Laurel Hill FL 32567
4
3
2
Single-Family
Listing courtesy of SUN REALTY and The Property Group 850 Inc
Show all 14 properties
EmailSMS
© 2026 RateMyAgent