WOLFEBORO — Henry Maxfield Sr. started HS Maxfield Real Estate in 1954, which is now celebrating 70 years of serving the Lakes Region.
The business is now overseen by Wolfeboro native Henry Southwick “Chip” Maxfield, Jr. — who was born on May 15, 1951 at Huggins Hospital. He is the son of Henry Southwick Maxfield, Sr. and Elizabeth (Betty) Maxfield.
Chip graduated from the Holderness School in 1969 and went on to graduate from the University of New Hampshire. Instead of following in his father’s footsteps, Chip explored the possibilities of clothing retail in Boston. However, his love of Wolfeboro and Lake Winnipesaukee soon lured him back home. Chip joined his father, Henry Sr. in real estate sales and land development.
In 1975, Chip became a full-time member of HS Maxfield Real Estate. He thrived on, and met with ease the challenges presented by the ups and downs of the real estate market. He found he enjoyed meeting with people from all different walks of life. Chip and Christina (Tina) Suzanne Franz married in Wolfeboro on Oct. 2, 1976.
When Henry S. Maxfield Sr. retired in the early-1980s, Chip took control of HS Maxfield Real Estate, changing the name to Maxfield Real Estate, Inc. The couple moved into a small Cape Cod home on South Main St., across from Kingswood Golf Course, and used the front of the house as an office. As the business grew, so too was the need for additional office space.
“It was a great day when with Tina, we moved the offices to Railroad Ave. in downtown Wolfeboro,” he said.
Chip also expanded the agency’s territory with offices in Ossipee, Alton and Center Harbor, becoming the Lakes Region No. 1 Independently Owned Real Estate Company.
Throughout the years, Chip has instilled a culture true to his business ethics. Agents and office staff are more than employees, they are family, and they are loyal.
When asked about his role as manager, Chip said, “The most difficult part of management is dealing with customers who are your friends, working with good friends, and one broker to man the office.”
Over the years, Chip has served on a variety of committees and boards as well as contributing to local fundraising initiatives.
With Chip’s initiative, sense of responsibility to community, and his genuine nature for giving back, the highlight of his community involvement is the creation of the “WE CARE” program. Initially established as a one-year charitable program in honor of Maxfield Real Estate’s 45th year in business was a way “to help support communities that support us.”
Looking at the books, he approached agents and presented his idea. All agents were on board. As of 2023 the “WE CARE” program at Maxfield Real Estate has raised over $1.5 million for 459 charities.
Chip is now in retired and remains owner of Maxfield Real Estate.

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