Kaye Browning Chastain

Dr. Cindy “Kaye” Browning Chastain, 80, of Windermere, passed away on February 21, 2024, with her daughters by her side.

She was born in Pontotoc, Mississippi, on March 23, 1943, and is the daughter of the late Linton Brantley and Mabel Pauline (West) Browning. Kaye graduated from Pontotoc High School, where she was a cheerleader and elected Miss PHS her senior year. Until the end of her life, she maintained strong friendships from her childhood and educational years. Earning a degree in Vocational Home Economics from the University of Mississippi, Kaye was recruited by the Orange County Public School system directly out of college. At Ole Miss, she was a member of Delta Gamma Fraternity.

Her continued activity in Delta Gamma also included her daughters, Alison and Amanda. Kaye regularly attended national DG conventions and was recently honored with her 50-year membership pin from the Fraternity. She was a devoted mother while working full-time and simultaneously earning her master’s in education from Rollins College and her doctorate in education from Nova Southeastern University. Her long and distinguished career with OCPS included serving as a county administrator and the Director of Winter Park Tech and Orlando Tech.

She was an active member of First Baptist Church of Windermere for over 50 years and extended her love of education to her church establishing the FBCW daycare and serving as a leader of the Girls in Action program. Kaye relished her time with her devoted church Sunday School class. Kaye enjoyed her membership with Florida Citrus Sports, remaining a die-hard Ole Miss Rebel fan her entire life.

In her retirement years, she also enjoyed her membership in the Bloom and Grow Garden Society, making frequent visits to her hometown in Mississippi, and spending time with her beloved grandchildren.

She was preceded in death by her husband of 44 years William (Bill) Russell Chastain and daughter Amy Ellen Chastain. She is survived by her two daughters, Amanda Chastain Gufford (Jennifer) and Alison Chastain Brackins (Patrick); and four grandchildren, Courtney Catherine and Brantley Porter Gufford, and Russell Jackson and Reese Chastain Brackins, all of Orlando. She is also survived by her brother Ron Browning of Destin and son-in-law Charles Gufford of Orlando.

Services will be held Monday, February 26, at Family Church-Windermere Campus, 300 Main Street, with a viewing at 10 a.m. followed by an 11 a.m. service. Memorial donations may be made to Delta Gamma Fraternity or Windermere First Baptist Church. Arrangements are being handled by Woodlawn Funeral Home & Memorial Park.

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