About Us

Company Info

Midland Agency Insurance was founded by Ray Flemming in 1985. The company was founded on the principles of integrity, hard work, attention to detail and a high priority on personal relationships. We are proud to say that many of the farmers that started with the Midland Agency in 1985 are still with us today.

Although our roots run deep in agriculture, we have expanded our services over the years. Matthew Flemming, Ray’s grandson, came to work at the Midland Agency in 1998, taking over the business in 2003. Over the years, he was approached by friends and family struggling to make sense of their insurance needs. With the same emphasis on relationships that have been our hallmark; Matthew expanded the scope of the company to include both commercial and personal lines of insurance. This side of our business has grown considerably over the 17 years as our customers have grown to appreciate the personal way we do business.

Our Agents

Ray Flemming

Ray Flemming

Ray Flemming was the founder of Midland Agency Insurance. He was raised on the farm near Gable, SC where integrity and work ethic were instilled in him at a young age. Ray graduated from Clemson University in 1948 after having his education interrupted by 4 years of proud service in the U.S. Navy during WWII.

Upon graduation, Ray become an Assistant County Agent with the Clemson Extension Service. A few months later, Ray was promoted as a State Extension Marketing Specialist with an emphasis on fruits and vegetables. In 1956, he stepped into the private sector as a sales agent, working with farmers from Florida to Pennsylvania. In 1962, he opened his own company in Columbia, with a winter office in Florida which specialized in international produce brokerage as well as the production and importation of vegetables from the Caribbean.

In 1980, Ray joined the Federal Crop Insurance Regional Office in Columbia where he worked with farmers all over South Carolina working in all phases of crop insurance as the Quality Control Coordinator. In 1987, at the insistence of many of Ray’s farming friends, he was licensed to sell insurance and Midland Agency was born shortly thereafter.

He built this business on hard work, honesty, and the personal relationships that have always meant so much to him. Almost 25 years later, we are still doing business the same way – by serving the farming community with great enthusiasm and joy.

Matthew Flemming

Matthew Flemming

Agent, Columbia Office

Email: matthew@midlandagency.com
Office Phone: 803-788-1312
Cellphone: 803-767-1000

Matthew Flemming, Ray’s grandson, began working with Ray in 1998 and is now the owner and president of Midland Agency Insurance. He was raised in northeast Columbia, SC where he graduated from Spring Valley High and later The College of Charleston. Matthew is married to Sissy Hawkins Flemming of Chesnee, SC. They are the proud parents of four children, Jacob, Maddie, Isabella, Mia Colson, and are in the process of adopting two sweet girls.

Matthew is an avid duck and deer hunter and saltwater fisherman. He loves the game of golf and is a member of Spring Valley Country Club. He and his family are active members of Shandon Baptist Church.

On the board of directors of – crop insurance professionals of America
Legislative committee – CIPA
Agent representative – on board of Rain and Hail society
Committee member for SCDA Flood relief

DIFFERENT WORKING GROUPS FOR the FARM BILL, t-yields, perennial crops, and others to promote the best products offered to farmers.

Organization Affiliations
SE Fruit and Vegetable

Amy Harris

Amy Harris

Agent, Columbia Office

Email: amy@midlandagency.com
Office Phone: 803-788-1312
Cellphone: 803-847-9294

Amy Harris was born and raised in Sumter, SC. She graduated from Saint Leo University in Atlanta, GA. Amy has been in the insurance industry since 2011 and has written business in Alabama, Georgia, North Carolina, and South Carolina. Amy joined our team at Midland Agency in September of 2014. She focuses on Personal and Commercial lines, as well as Crop and Agribusiness Insurance.

Amy is a proud mother of two children. She enjoys spending time with her family and friends.

Peggy Dart

Peggy Dart

Agent, Columbia Office

Email: peggy@midlandagency.com
Phone: 803-788-1310

Margaret (everyone calls her Peggy) was born in Charlotte, NC but considers Columbia, SC her home.
After attending USC, Peggy worked for a few large corporations and for the last 20 years has been an Insurance Agent.

She received her CIC designation – Certified Insurance Counselor – in 2009.

Peggy enjoys playing with Sammy and Buster (her two yellow labs), going to movies, bookstores, shopping and discovering new restaurants. She lives in the Northeast area on three acres with a lake and is on the board of her homeowners’ association.

Stacey Martin

Stacey Martin

Agent, North Carolina

Email: stacey@midlandagency.com
Phone: 704-201-6485

Stacey Martin was raised in New Salem, NC, and has been a resident of the Anson, Cabarrus, Stanly, and Union County area his entire life. Stacey has over twenty years of experience in the farming insurance industry, as well as a vast background of the crops grown in the Piedmont region of North Carolina. He is married to Johanna Drye Martin, of Oakboro, NC, where they currently live on her ancestral family farm. Together they have six children: Elizabeth, Abigail, Thomas, Preston, Naaman, & Carley.

Stacey is an accomplished musician, and enjoys spending his free time playing music, woodworking, and tending his hobby farm. He and Johanna attend Pleasant Hill Baptist Church, where they both minister with the praise and worship band.

Contact Us

Matthew Flemming with Midlands Agency Insurance is my crop insurance agent. I can 100% say that there is no other agent that has worked harder to protect and administer peach insurance in the South.  His company specializes in all types of crop insurance and they offer a wide range of other insurance products.

Titan Farms

I have used Midland Agency Insurance for all of my insurance needs, personal and commercial, over the past several years. I have never been disappointed with the quality of the products or the service I have received.

The Tuna Company LLC

I just wanted to express my sincere appreciation at how hard Agent Peggy Dart worked to find my company the best insurance coverage. I am truly grateful for all the time and effort she put into all my policies and making sure I was covered correctly.

Ice House SC LLC

I have been a client of Amy Harris’ for the past 2 years and I have to say, Amy is extremely accommodating and hardworking. If she cannot give you an answer right away, she always gets back to me in a timely manner. It is clear that she is there to make sure I have the right coverage that works for my family.

Kevin and April Hendrix