Diane Rae Pressley

Diane Rae Pressley, 72, of Winter Garden, Florida, passed away peacefully on August 17, 2025, surrounded by her loving family. Born on September 26, 1952, in Somers Point, New Jersey, Diane lived a life defined by love, devotion, and family.

Diane dedicated her life to her children and grandchildren, who were the center of her world. She rarely missed a sporting event or family celebration, always showing her unwavering support and pride. Her happiest moments were spent surrounded by her family, especially on cherished trips to Sanibel Island, where she found peace and joy by the water.

Known for her fierceness, goofy sense of humor, and genuine love for her family and friends, Diane created a family that is rooted in love, laughter, and traditions that will live on for generations.

While she will be deeply missed, Diane’s love and presence will live on in the hearts of all who were blessed to know her. Diane is survived by her husband Robert Pressley, daughters Tracey Sartini and Michele Crouse, son-in-law Raymond Crouse, grandchildren Anthony Sartini Jr., Allison Sartini, Gianna Crouse, and Jakob Crouse, sister Grace Becker, brother Walter Pfirman Jr., and beloved nieces.   

All are welcome in joining us to celebrate Diane at Woodlawn Memorial Park and Funeral Home on September 27, 2025, at 10:30 a.m. The celebration of Diane will continue at the Crooked Can Brewery Company/Barrel Room in Downtown Winter Garden immediately after.

In keeping with Diane’s love for the ocean and island spirit, please join us in wearing your best island-inspired attire in her honor.