In Memory of




Obituary for Michael A. Howland

Michael A. Howland, Age 89, of Winchester, Massachusetts, passed away peacefully on the morning of November 25, 2023 surrounded by his loving family. Michael is survived by his wife of 67 years, Lorraine (Anderson) and daughters Lori Davis, Jacqueline Richardson of Winchester, and Cindy Howland of Concord. Grandfather to Jess Zweifel of Charlotte, NC, Katie Piluri of Woburn, Michael Davis of Beverly, Kristen Howland Richardson, Ryan Howland Richardson of Winchester, Lillian Howland of Concord. Great Grandfather to Max and Zoe of Charlotte, NC. Brother to Shirly Shicker of Reading. Michael was predeceased by his Parents Charles and Lillian and his siblings Frederic, William, Charles, Richard, David, Beverly and Gene.

Michael was always conscientious and an extremely hard worker whose thirst for success could almost never be quenched. As a young boy, he would always find a way to earn money which enabled him to buy Popsicles for his teething baby sister or Christmas presents for his nine siblings who all grew up with much poverty. His siblings were in such poor shape the state of Massachusetts Welfare Agency stepped in and placed them in an orphanage. From the orphanage the children were separated and placed in different foster homes. At age 9 Michael settled with a foster family from Stoneham where he was raised by a loving family.

Growing up in Stoneham he was a Boy Scout and played varsity basketball and always attended church where he taught children the Bible. His desire to make money meant he always had a job which allowed him to buy a car (even before obtaining his license) which he would famously race his peers.

After graduating High School, he found work at the GE plant in Lynn and then happened upon a home improvement company where he talked his way into being hired as a roofer, which he had absolutely no experience doing. The owners of the business immediately recognized his gift for persuasion and made him a salesman where, with a borrowed jacket and tie, he excelled in generating more sales for the company. He was so successful he eventually bought Perma Home Corporation outright. He grew the aluminum siding business and became one of the biggest “Tin Men” in New England from the 1950’s to the ‘70’s. Never satisfied and always wanting more, in 1978 he saw a development opportunity and built his first commercial property for Alcan Aluminum in Woburn, MA. He formed Howland Development Company which is now one of the leading commercial real estate companies with over 1.6 million square feet of office and industrial space.

He loved listening to Jimmy Buffett while cruising the Caribbean on his yacht the "Lori H" and he epitomized the lyric “I used to rule my world from a pay phone” for no matter where he was in the world he was in contact with his office on a daily basis. His Work Hard, Play Hard attitude was always clearly evident in his everyday life.

Michael was a devoted family man and always put those he loved first. He found immense joy in spending time with his wife, children, grandchildren and great-grandchildren participating in many activities and spending time at their various vacation homes. From freestyle skiing in Waterville Valley, NH, to cruising through all the Virgin Islands on his 86-foot yacht, to spending time on the water at his homes on the picturesque island of Martha’s Vineyard and Boca Raton. These places were so dear to him for the family memories that were made. In his free time, he also enjoyed playing golf and tennis with treasured friends at the Winchester Country Club, the Wianno Club, Delray Beach Club, FL, a founding member of the Royal Palms Yacht Club and former director of the Algonquin Club. He found immense joy in sharing his globetrotting adventures with his family enabling them to enjoy culturally rich life experiences.

His empathy was boundless, and he was a beacon of generosity both financially and emotionally, making him a source of support for those in need. Michael exemplified strength and perseverance and was forever grateful for the support and care provided by the Mass Society for the Prevention of Cruelty to Children.

Visitation will be held at the Lane Funeral Home, 760 Main St. (Rte. 38) WINCHESTER on Thursday, November 30th from 5-7pm. A Funeral Service will be held at the First Congregational Church, 21 Church St., Winchester on Friday, December 1st at 1pm. Relatives and friends are kindly invited to attend. Interment Wildwood Cemetery, Winchester. Memorial donations in Michael’s memory may be made to Mass Society for the Prevention of Cruelty to Children, 125 Hartwell Ave., Lexington, MA 02421. For online condolences please visit