Carol B. Hollenbeck

Carol Bernice Hollenbeck, age 89, peacefully passed away on September 24, 2026—a date of profound significance, marking her 71st wedding anniversary to her beloved husband, Lee.

Born in Milwaukee on September 19, 1937, to Bernard and Edna (Schupinsky) Houting, Carol entered the world with an inherently resilient spirit. Never having had the chance to meet her father, who passed away before her birth, she developed a fierce determination and an adventurous heart that guided her through a vibrant, accomplished life.

Carol was a dynamic force in the Wisconsin real estate industry. As an accomplished real estate saleswoman, her keen business mind and vision helped shape the landscape of Waukesha County. Her real estate career culminated in two major luxury condominium developments in Hartland, Wisconsin. The first was the development of her ancestral hunting land on Nagawicka Lake called Nagawicka Shores, where Carol and Lee have enjoyed living for the last 15 years. The second was a larger development called Oak Ridge. Her entrepreneurial drive remained vibrant throughout her entire life.

True to the title of her memoir, Carol was an avid adventurer who truly thrived when "sailing through life." She was a passionate competitive sailor, from small boats on Lake Nagawicka to racing their 42-foot sailboat across the waters of Lake Michigan with her friends and family. She also loved cruising the open waters of the Great Lakes and the Gulf.

That deep love for the water extended well beyond the sails. In Florida, Carol and Lee traded canvas for horsepower, enjoying many fun-filled years of power boating alongside dear friends in the Naples Cruise Club and Naples Sailing & Yacht Club.

On land, her competitive fire was just as bright; she was a very skilled athlete and a two-time National Women’s Curling Runner-up, a testament to her focus, teamwork, and sharp wit. She also enjoyed many decades of tennis, water skiing, swimming, and golfing, including four hole-in-ones!

Always carrying a touch of wanderlust, Carol and Lee ventured to Florida in 1989, seeking a place to ultimately retire. They found Foxfire, a beautiful golf and tennis community in Naples, Florida, and instantly fell in love with it. Over the course of 37 vibrant years there, enjoying the sunshine and many activities, it was truly the wonderful, deep friendships that captivated Carol and Lee.

Her love for creative thinking and her focus on legacy culminated in the authorship of two published books: Our Yesterdays, the story of her ancestry, and Carol’s life story, Sailing Through Life. In its pages, she captured how she faced life's calm seas and stormy waters alike with unwavering courage, humor, and a deep Christian faith. For anyone wishing to understand her vibrant heart, her books tell the story best.

Carol’s greatest joy, however, was the family she and Lee raised. She is survived by her devoted husband, Lee Hollenbeck, and their four children: Richard (Cindy) Hollenbeck, Steve (Bobbe) Hollenbeck, LeAnna (Brendan) Wall, and Dan (Laura) Hollenbeck. She was the cherished grandmother of 10: Garrick (Missy), Darren (Weiya), Gordon (David), Andrew (Brian), Xander, Grace (Trevor), Zachary (Daria), Joshua, Samuel, and Hannah; and the proud great-grandmother of eight: Ethan, Parker, Juliet, Micah, Asher, Kaylee, Caleb, and Harper. She is also survived by her sister, Susie Varney, and many dear nieces, nephews, and countless lifelong friends. She was reunited in heaven with her parents and six of her seven siblings.

To celebrate Carol's wonderful life, two memorial services are being planned. A celebration of life will take place in Naples, Florida, in January 2027, followed by a northern home celebration in Delafield, Wisconsin, in the summer of 2027. She will then be laid to rest in the Delafield Cemetery.

In lieu of flowers and to honor Carol’s legacy, memorials in Carol’s name may be given to Foxfire Legacy Fund by mailing a check to 1030 Kings Way, Naples, FL 34104.