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Roy Wright Caldwell

1927 - 2025

Roy Wright Caldwell obituary, 1927-2025, Clermont, FL

BORN

1927

DIED

2025

FUNERAL HOME

Becker Funeral Home - Clermont

806 W. Minneola Ave.

Clermont, Florida

Roy Caldwell Obituary

Roy W. Caldwell, beloved husband, father, and grandfather, passed away peacefully on Sunday, March 9, 2025, at the age of 98.


Born in Trapnell, Florida on January 17, 1927, Roy dedicated his life to serving others. He served in the Navy before going to University of Florida, where he graduated from law school. During this time, he dated and married his cherished wife, Marion Ann, who was attending Stetson University. They lived in Jacksonville and Tavares – where he served as mayor – for a short time before building a house in Clermont in 1959. He practiced law in Clermont, ran multiple times for public office, was the Clermont and Minneola city attorney, and was a Lake County judge at the end of his career. After retirement, he went back to the law; but just for friends, family, charities, and his church, the First Baptist Church of Clermont where he was a member for over 65 years.


Roy’s deep, rich voice could be heard from the choir for many years, he was instrumental in planning every inch of the old church campus, and he sat in various leadership positions over the course of his life. The First Baptist Church of Clermont will miss a man like Roy, who never charged a dime for years of legal work.


Roy loved the Gators and travelled near and far to all the games. Football was the big show, but he supported all Gator athletics and took his kids and grandkids to many sporting events. He was a proud member of the Gator Booster Club and the UF Alumni Association.


Roy is survived by his wife, Marion Ann Caldwell, his children, Jimmy (Mary Beth) Caldwell, Merry (Phil) Penn and Irvin (Debbie) Caldwell and his brother, Robert Caldwell. He is preceded in death by his son, Sparky (Marla) Caldwell. He leaves behind ten grandchildren: Jenna Leigh (Brian) Burger, Casey (Julie) Caldwell, Kevin (Stephanie) Caldwell, Joe (Katie) Caldwell, Kristoffer (Courtney) Caldwell, Melissa Ann (Jared) Hester, Cassidy (Justin) Densmore, Brian Penn, Chloe (Julian) Mulkay, and David Penn. He has 16 great-grandchildren.


A memorial service will be held on Thursday, March 20 at 11am at The First Baptist Church of Clermont on Hartwood Marsh Road. This is the new location.


Roy’s legacy of service, faith, and love will live on in the hearts of those he touched. He will be deeply missed but never forgotten.


Go Gators!

Published by Becker Funeral Home - Clermont on Mar. 13, 2025.

Memories and Condolences
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Kris Caldwell

April 3, 2025

My grandfather was such a large figure in our lives and a model . Through his compassion to others and constant drive for knowledge and understanding of this strange world, I am proud to have learned from grandpa. He has provided me with a roadmap for how to deal with the difficulties we face in life and I can only hope to be as great a man, father, brother, grandfather and citizen. Rest in peace and may your eternal heavenly life be as impactful as your time here.

Ken amd Martha Lowery

March 21, 2025

We are so sad! Roy and MarionrAnn have been our precious friend ever since they moved to Clermont! Many wonderful memories with Gator games, traveling and all our church activities! Such fun watching the children grow to be such wonderful young people that loved their parents so much
L and each other so much! Love to you Marion Ann!!

Cheryl Olivenbaum

March 19, 2025

He was a Great, Wonderful Man that I was Very Lucky to have known.

Lisa & Madison Cartee

March 19, 2025

Prayers for Marion Ann and the family. God Bless

Terry Woodford

March 18, 2025

Irvin and family, I'm sorry to hear the passing of Mr. Caldwell. It's obvious he was very loved as a husband, father, grandfather and friend. Hold tight to his memories and may they comfort you in the future.

Ann and Buddy Forehand

March 15, 2025

We were privileged to know Roy while living at The Oaks condominiums, both of us serving on the Board of Directors with him over the years. RIP Roy

Roddy Conner

March 14, 2025

Mr. Caldwell was a dear and cherished family friend of more than 70 years. I admired him greatly and have so many fond memories of my parents and the Caldwell family. He was a wonderful Christian Gentleman and also an ardent GATOR Fan! Roy is HOME with Christ. I will be forever grateful for his kindness to me and especially my parents!
Roddy Conner

Chloe Mulkay (Caldwell)

March 13, 2025

My Grandfather was a special man with a giving heart and I’m honored to be his granddaughter and share in his legacy. He will certainly be missed this side of heaven, but I have so much joy knowing he is with my Dad and in the presence of Jesus!

Keith(Cooter) Ward

March 13, 2025

I'm sorry to hear the news of Mr Caldwell passing. I've always had respect and admiration for him. Truly a pillar of the community and an excellent example of good character. May the grace of our Lord Jesus Christ be with you.

Lisa Antos

March 12, 2025

Irvin and Caldwell family please know I am keeping you all in my thoughts and prayers. How blessed you were to have had him in your life for 98 years. May he rest in peace and may you all be comforted by the memories of Roy.

Shirley Liming

March 12, 2025

Caldwell Family,

I am sorry to hear of Roy's passing, May the memories linger on.

McKenna Family

March 11, 2025

Dear Caldwell family,

Our deepest condolences on the loss of Mr. Caldwell.May you find peace and comfort during this difficult time.

With sympathy,
The McKenna family

Rachel Eller

March 11, 2025

RIP Judge Caldwell. I consider myself along with many to have known you for so many years. A truly wonderful man.

John Fillingim

March 11, 2025

Mr. Caldwell will be dearly missed. I have so many great memories of him as a kid growing up in Clermont. He took me to my first Gator game and from that day I was hooked. He loved to drive fast and keep the air conditioner cold. We fondly referred to the temp in his car and home as “Roy Cool”, and that’s a trait I picked up from him. His bold voice and stature is something that I’ll never forget. God Bless Mr. Caldwell and the entire family. He lived a long and great life and now it is his time to rest in peace with the Lord.

Herbert (John) Greenlee, Jr

March 11, 2025

Roy was a good friend to me from the time I moved to Clermont. He assisted me in getting my LaSalle Extension University LLB degree and was a long-time client of my accounting firm. My condolences and best wishes to his family.

Bill BUESING

March 11, 2025

It was an Honor and Privilege to know Mr Caldwell. It was always a pleasure to stop by his home every two weeks, as his Schwan man. Mr Caldwell was always in good spirits and we always had great conversations. RIP SIR.

Casey Caldwell

March 10, 2025

I wasn’t as close to my grandpa in the last several years as I would have liked to be, but the memories we shared will always hold a special place in my heart. One of the ones I treasure most is the trip to Washington, DC, with my cousins. It was during that trip that Grandpa taught us how to read and navigate with a map—a skill I really didn’t enjoy at the time (and I’m sure he didn’t either, since we got lost a few times!). What seemed like a small thing then has stayed with me ever since. That lesson in navigation didn’t just teach me how to get around on a map; it taught me perseverance, how to find my way even when things didn’t go as planned, and how to push through life’s challenges.

Grandpa was always firm, but so kind, and his advice—though it wasn’t always what I wanted to hear—was always what I needed. He had a way of guiding me with love and wisdom, even if it wasn’t the easiest path to follow.

My kids also loved spending time with him. They especially enjoyed walking down the dock to feed the fish with great-grandpa—those simple moments were so meaningful to them.

Though Grandpa wasn’t part of every moment in my life, the lessons and memories he left behind are ones I’ll carry with me always. His wisdom, his love, and his way of teaching will stay with me and my family until we meet again. Until then, I hope grandpa and dad are catching up on all things Gator football!

March 10, 2025

Sympathies to the family of Roy Caldwell

Marla Caldwell

March 10, 2025

This man has been an important part of my life for nearly 40 years. That is when I fell in love with his son Sparky. Roy was a wonderful father in law and was a man of integrity and intelligence, generosity, quick wit and humor and full of love for God, his family and his country. I had the absolute privilege of my lifetime to be one of his caregivers for a portion of his latter years with us. This is when I fell in love with Gaither music. Roy sang his heart out every single day, worshipping God even with his advancing dementia. It broke my heart when he passed, but knowing he is with his Lord and Savior Jesus and his son Sparky turns all of that heartache around instead, to a time of celebration and rejoicing. Roy is finally at home. I know he ran to Jesus with eyes and arms wide open and a heart full of readiness. He will be missed tremendously here on earth but I am confident we will all be reunited one day in God’s timing.

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Memorial Events
for Roy Caldwell

Mar

20

Memorial service

11:00 a.m.

The First Baptist Church of Clermont

Hartwood Marsh Road, Clermont, FL

Funeral services provided by:

Becker Funeral Home - Clermont

806 W. Minneola Ave. P.O. Box 120864, Clermont, FL 34711