08/17/2025
It is with heavy hearts that we say goodbye to our friend and the man who shaped not just this company, but all of us who were lucky enough to work alongside him—Henry 'Chip' Maxfield, Jr.
Henry Southwick “Chip” Maxfield, Jr. was more than a real estate icon—he was the heart and soul of Maxfield Real Estate. Born at Huggins Hospital in 1951, Chip was a true native, whose roots ran deep into the granite of New Hampshire and the waters of Lake Winnipesaukee. Raised by Henry Sr. and Elizabeth “Betty” Maxfield, Chip carried forward a family tradition that began in 1954 with the founding of H.S. Maxfield Real Estate.
While he briefly ventured beyond the lakes and mountains to explore Boston’s retail world, Chip was always drawn home—to the place and people he loved. He returned to join his father in real estate, where he brought energy, vision, and an uncanny ability to connect with everyone he met. He was as comfortable guiding first-time homebuyers as he was leading major development projects, and he treated every client like family.
When Chip took the reins in the 1980s, he didn’t just inherit a business—he transformed it. He led with authenticity, integrity, and a passion for community that would define his leadership. He and his wife Tina turned their small Cape on South Main Street into a thriving office, before relocating to Railroad Avenue—the move Chip fondly called “a great day.” Under his guidance, Maxfield grew to become the Lakes Region’s #1 independently owned real estate company, expanding into Ossipee, Alton, and Center Harbor.
But Chip’s legacy extends far beyond sales. He built more than a business—he built a family. His team of agents and staff weren't just coworkers; they were part of something larger. He fostered loyalty, generosity, and a spirit of collaboration that still defines Maxfield Real Estate today.
Chip's service to the community was just as impactful. Whether he was co-founding the Abenaki Water Ski Club, leading the Great Waters Music Festival, or launching the enduring “WE CARE” charitable initiative, Chip never stopped giving back. His honors—from the General James Wolfe Award to the Union Leader’s Legacy Award—speak to a life spent lifting others up.
In every role—father, husband, boss, mentor, friend—Chip led with grace, humility, and joy. He believed in hard work, in laughter, in showing up, and in making things better for those around him. His love for Wolfeboro wasn’t just nostalgic; it was active, present, and powerful.
Today, we honor a man who built homes, both literally and figuratively. Chip Maxfield’s legacy lives in every agent he inspired, every family he helped, and every life he touched. We are proud to continue his work and walk the path he cleared—with gratitude in our hearts and Lake Winnipesaukee always on the horizon.
With love and remembrance,
The Maxfield Real Estate Family
