David Alan "Houseboat" Winter's Obituary
David Alan Winter was born on August 11th, 1970, to Donald Lee and Sharon Kay (Ouellette) Winter. He joined brother Michael, sister Rhonda, and twin brothers Mark and Scott whom he idolized. He was born in Bay City and spent the first decade of his life in the Beaverton and Albright Shores area of Michigan. In the early eighties the family moved to Lehigh Acres Florida where David attended Alva Middle School and Riverdale High School.
David leaves behind many stories and accomplishments. The kind of stories that make you laugh until you cry, shake your head in disbelief if his twin brothers were involved, or just smile as you remember his kindness. One of his proudest childhood achievements was being named Home Run King of South Florida over forty years ago. He would fondly remember hitting any pitch sent his way far over the outfielders and beyond the fence.
David carried a few notable nicknames, some knew him as Big Dave, Houseboat, and Baby David to his big sister, Aunt Mary Glowiak, and other family members.
David had a large presence that didn’t go unnoticed as all 6’4” of him entered a room. His size worked to his advantage when he worked in his father’s pawn shop and used car dealership (Wheeler Dealer) as a repo man alongside his brothers Mark and Scott. He also did many security jobs throughout his life where he gathered a vast collection of band and movie memorabilia as well as entertaining memories.
In 1995 David married Tracy Ruth Kent. The couple took up residence in North Fort Myers. Through the upcoming years, they opened their home and hearts to Tracy’s sister Tara as well as David’s niece Samantha and her sister Mikayla. The marriage sadly only survived a decade, but they remained close friends and co-parented well.
The most important role in David’s life was being a father. In 1999, the couple welcomed son Kaegan Ryan who is currently serving in the United States Marine Corps. David was beyond proud to talk about Kaegan to anyone that would listen. He was very excited about an upcoming move to be closer to Kaegan. Britton Gianna Deleacaes is Kaegan’s little sister, and she shared a very close connection with David. He was her DD and she was his Brit Brit. David’s big heart easily adopted Britton from her very first day on this earth. They were making plans for him to attend her college graduation next week.
David loved his family. He was happiest when surrounded by the people he loved, sharing meals and making everyone laugh with playful spirit. His heart and sense of humor were equally as large as he was. He never met a stranger, always had a smart comment ready (whether asked for or not), and had a way of making people feel welcomed by just being himself. He loved fiercely, forgave easily, and collected lifelong friends everywhere he went.
David and his father Don were avid scuba divers years ago and did many dives together throughout Florida and to Mexico. They shared a close bond along with David’s brother Scott. The three built and lived together in their dream house which could easily be considered a bachelor’s delight. It was filled with interesting artifacts that they had collected through the years, stories that somehow got bigger every time they were retold, and sharp-tongued wit.
He is survived by his father Donald Winter of Bradenton, FL, Mike (Kim) Winter of Lansing, MI, Rhonda (Mike) Yoder of Houston, TX, Scott Winter of Bradenton, FL and many numerous nieces, nephews, and close friends that were like family.
He was preceded in death by his mother Sharon, his brother Mark and his beloved faithful canine buddy, Jamal.
If David could leave us with advise, he’d say to hug the people that love you, forgive a little quicker, then smirk and boldly ask, “How ‘bout them Cowboys?” despite their less than stellar performances.
A Celebration of David’s Life will be held on Saturday August 1st, 2026, from 11:00 A.M. – 1:00 P.M. at Fort Myers Memorial Gardens, Colonial Family Center, 1589 Colonial Blvd., Fort Myers, FL 33907.
Though our hearts are broken, they are also full – full of gratitude for having known him, loved him, and laughed with him. We will miss him and we’ll carry his love in our heart each day.
What’s your fondest memory of David?
What’s a lesson you learned from David?
Share a story where David's kindness touched your heart.
Describe a day with David you’ll never forget.
How did David make you smile?