Tom Winter

Thomas Dean Winter was born on February 3, 1953, to Harold and Lorraine (Hauglid) Winter in Pipestone, Minnesota. He was raised on the family farm near Cazenovia, Minnesota. He attended Hill Elementary School and later Central High School in Pipestone, graduating in 1971. After attending technical college, Tom began his career working at a bank in Glenwood, Minnesota, where he met Judy (Christman). They were married on August 20, 1976, and together had three children Janna, Gavin, and Ivy. They remained married until 2004, when their individual journeys prompted their relationship to evolve.

In 1982, Tom returned home to Pipestone, where he began working at Key Agency while simultaneously opening Winter Realty, Inc., a real estate brokerage that has served his community for 43 years and counting—25 of those years alongside his son, Gavin. Tom’s skillset helped broker and facilitate thousands of deals over his career, not only helping families find their homes but also helping shape the Pipestone community as it exists today.

In addition to his respected business acumen, Tom had a love of farming. After purchasing his family farm in Troy Township in 1991, he farmed for around 10 years, often citing that more deals were done on his Motorola bag phone in the tractor cab than during all of his office time combined.

Tom was a member of St. Leo’s Catholic Church. His faith was his own, and he lived in a way that treated others with respect and acceptance, never asking them to be anything more than who they were. Over the years, Tom was involved in a multitude of boards and committees, donating countless hours and resources in an effort to better the community that had always been his home.

Tom was an avid recreational golfer. In addition to playing in three leagues on Tuesdays—often in his cut-off T-shirt and golf sandals—he routinely took an annual golf trip with his close friend Bruce Kocourek and a rotating host of others. If not golfing, attending classic rock concerts, or working, Tom’s love of farming kept him playing in the dirt.

A place for everything, and everything in its place—Tom’s shop(s) were the stuff of dreams for the “do-it-yourselfer.” Large equipment, aerial lifts, and mowers for any terrain—it was often thought that if there wasn’t something to do, he would create it anyway.

Somewhere in between, Tom met Carla Bruning in the fall of 2012. The two found each other at just the right intersection of life, and along with her four children, Tom’s purview of family expanded. Even to his last breath, Carla was woven into the happiest parts of his life. As a couple, they traveled, golfed, and enjoyed whatever life presented them. They shared a deep understanding of one another and often needed nothing but each other to be happy.

After a long battle with prostate cancer, Tom passed away peacefully in his home on Sunday, January 4, 2026 at the age of 72.

He is lovingly remembered, forever missed, and continuously credited by his three eternally grateful children, Janna (Dave) Galloway of Bemidji, Minnesota, Gavin (Jessica) Winter of Pipestone, and Ivy (Blake) Kolquist of Duluth, Minnesota; his grandchildren, Gwyneth, Makhi, Jack, Broderick, Kendrick, Sloane, Elyse, and Sydney.

Tom also shared a reciprocal love and caring relationship with Carla’s children, Corey (Amber) Bruning of Sioux Falls, SD, Jen Stone of Flandreau, South Dakota, Josh (Amanda) Bruning of Canby, Minnesota, and Abbie (Thomas) Metzler of Rapid City, South Dakota; along with his bonus grandchildren, Jade, Kassie, Mia, Lexi, Amelia, Vienna, and Garen.

He is further survived by his siblings, Gary (Joanne) Winter, Gayle Popma, and Shelly (Jon) Kozlowski, all of Pipestone; and his sister-in-law, Linda Winter.

He was preceded in death by his parents, Harold and Lorraine Winter; his brothers, Bill and Dennis Winter; his brother-in-law, Jerry Popma; and his nephew, Jamie Winter.