Animals loved him, bankers feared him, and his friends admired him for his loyalty. Sadly, after a brief but devastating bout with dementia, Dennis Stackhouse passed over to the big greenfield development in the sky on May 22, 2022 at the age of 79. 

Born on Oct. 10, 1942 and raised in Bridgton by his beloved parents Dorothy and Clayton Stackhouse, he attended Holten High School in Danvers and went onto the University of Massachusetts in Amherst. There, he excelled at writing friends’ papers and succumbing to the mischief of the Sigma Phi Epsilon Fraternity that earned him the nickname “Bobcat.”

Those who met him saw that he was friendly and smart, but those who knew him well understood his creativity and fearlessness. After a brief but distinguished career at Brigham’s Ice Cream, he spent several years at John Hancock, before starting Boston Realty Advisors. Specializing in commercial real estate, he adopted a focus on overlooked and underserved communities. Dennis redeveloped the Old Mr. Boston Distillery in Roxbury, navigated the cultural and legal eccentricities of the North End, became one of the first American real estate developers in China in 1985, and remediated and redeveloped several contaminated properties in the Liberty City and Opa-Locka communities of Miami into elderly housing, retail, and offices.

Dennis loved dogs, especially the late-model Basset Hound his son raised, and he particularly loved the underdog. His tenants were a potpourri of non-profit charities, dreamers, schemers, entrepreneurs, and organizations focused on women, children, and workforce development. Dennis saw the best in people, and he saw the best of the disregarded communities in which he built first class buildings. He spared no expense: “Brass & Glass,” as he called it, where granite and marble, crown moldings, inlaid wood, and mahogany paneling were featured in neighborhoods that others drove quickly past. He donated generously, forgave rent all too frequently, and let any number of shysters pray upon his gentle heartstrings. In the end, he had more pride in his projects than their returns, leaving his lenders begging for mercy.

Miraculously, he survived several downturns in his career, including a devastatingly unfounded allegation of fraud that was eventually dropped by the courts, and managed to recover, thrive, and grow. Dennis was resilient above all else, and in his own quiet way, a fighter. It seemed he never lost a night of sleep, no matter how stressful the situation or overwhelming the odds. He loved his work, but spent his downtime voraciously reading, bombing down the slopes of Killington well into his 70s, and drowning the flowers in the garden to the chagrin of every landscaper and neighborhood green thumb who begged him ‘to stop with the hose.’

As in horticulture, he was overly generous in philanthropy: He proudly supported the YWCA, Youth Co-op in Miami, and local youth football in Roxbury. He quietly gave money to people hard on their luck. He helped both the formerly incarcerated and people struggling with addiction to find jobs and make their rent; supported numerous day care, nursery, and elementary schools in the neighborhoods where he worked, and tirelessly helped the sick find treatment, pulling strings to get people care with the best doctors in the nation. He once helped pay for a 7-year-old Miami girl with bone cancer to receive an experimental expandable implant, ensuring that her leg would continue to grow. She went on to compete on her high school cheerleading team. 

While his counterparts in business flaunted their charity, Dennis told no one because his motivation was not recognition, but an innate sense of right and wrong. Sadly, this generosity was often exploited, and when his reputation was besmirched late in his career, he chose to fight quietly in the court system rather than publicly defend himself and set the record straight. 

He leaves behind his passion for literature in both his sons, Andrew and Brent, to whom he enthusiastically read “Treasure Island” at bedtime in a number of terrible pirate impressions and variations of a Scottish accent. Dennis also leaves behind his bride of nearly 50 years, whom he endearingly referred to as “Lynda with a ‘Y.’” Dennis will be missed mostly in this world by the countless number of friends and colleagues who were touched by his kindness, generosity, and mischievous humor.

A celebration of his life will be held in September. To RSVP, e-mail stackhousememorial@gmail.com. 

In lieu of flowers, donations may be made in Dennis’ honor for community dementia services at https://give.caringkindnyc.org/Stackhouse.

Arrangements by Hamel-Lydon Chapel & Cremation Service of Massachusetts, 1-617-472-5888, HamelLydon@gmail.com