Cover photo for Harley Cheshire, Sr.'s Obituary
Harley Cheshire, Sr. Profile Photo
1937 Harley 2020

Harley Cheshire, Sr.

April 8, 1937 — September 6, 2020

Ocala


CHESHIRE, Harley Benjamin Sr.
Ocala - Harley Benjamin Cheshire, 83, passed away September 6, 2020 in Ocala, Florida. He was born April 8, 1937 to Leon Cheshire and Myra Prisoc Cheshire in White Springs, FL. and moved to Ocala shortly after. He served in the United States National Guard and worked in Sales in numerous industries throughout his life.


He is preceded in death by his parents; son, Robert E. Cheshire; brothers, Dwight A. Cheshire and James W. Cheshire.
He is survived by his loving wife of 53 years, Jessamine Gaye Cheshire; son, Harley B. Cheshire Jr.; daughter, Sandra L. Dillon (Tony); brother, Robert Wayne Cheshire; sister, Nyla Riner (Wayne); grandchildren, Chris Dillon (Kori), Andrew Dillon (Olesya), Evan Dillon, and Bethany Dillon; Great Grandchildren, Olivia Dillon, Alexander Dillon and Jaxxen Dillon, Hailey and Veda Eaton;  Great Niece, Sydney Fraser and several other nieces and nephews all of whom he loved dearly.


A Memorial Service will be held 6:30 p.m. Monday, September 14, 2020 at Grace Baptist Church, 10835 SE 70th Ave, Belleview, FL 34420. In observance of social distancing, the service will be held outside, please feel free to bring a lawn chair/folding chair.  Arrangements under the care of Countryside Funeral Home.

To order memorial trees or send flowers to the family in memory of Harley Cheshire, Sr., please visit our flower store.

Service Schedule

Past Services

Memorial Service

Monday, September 14, 2020

Starts at 6:30 pm (Eastern time)

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