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Leonard Trent Winfree
Funeral Time: Sunday, September 26th at 10:30AM
Leonard Trent Winfree, 68, of Lexington, KY, died Wednesday September 1, 2021. Born in Lexington on July 29th, 1953, Trent attended Tates Creek High School and graduated in 1971. In 1975, he received a Bachelor’s in Business from The University of Kentucky where he was a member of Sigma Alpha Epsilon Fraternity.

Upon graduating, Trent went to work for Andersen Windows & Doors for 35 years, living in Boise, ID and Woodbury, MN while with the company. Semi-retired in his beloved home of Lexington, KY, he spent the last 10 years as owner and operator of SquareFoot Construction in-home remodeling and new home construction.

With his lifelong background in the construction industry, Trent consistently and faithfully shared his experience with others in the building business. Through the Building Industry Association of Central Kentucky(BIA) he was active serving his local association, instrumental in establishing educational programs and most recently served as Chairman of the Remodeler’s Council.


Trent will be remembered fondly for his humor, charisma, wisdom, and kindness beyond measure. He was a friend and mentor to all who knew him.

Trent is survived by daughter Kathryn Winfree, fiancee’ Deborah Gullett, along with his- step-children Dustan Castro, Archer Scherer, Sara(Drew) Sterling, and Alison Gullett, step- grandchildren Austin, Logan, and Elizabeth Sterling, and siblings Woody Winfree(Russell Sidelsky) Tracy(Helen) Winfree, and Whit(Amy) Winfree. His parents were William Whitlow and Ann Tracy Winfree. Six nieces and nephews.

Family and friends are invited to attend a Celebration of Life gathering on Sunday, September 26th at Champion Trace Golf Course located at 20 Avenue of Champions, Nicholasville, KY 40356 at 10:30 AM. In lieu of flowers, the family ask that donations be made In Memory of Trent Winfree to the BIA Education Foundation by connecting to: http://www.biacentralky.com/trentwinfree.html Copy and paste to browser