About Us
Our company values mirror our family values. Honesty, Loyalty, Mutual Respect, Hard work and Support are some of the values that we lay as the foundation when developing a relationship with each of our customers. We will work hard as your Insurance Advisors to provide you with the best coverage for the best value. “We want to make you a Halstead Insurance customer for life!”
For over 45 years Halstead Insurance has been committed to its mission of providing the highest quality of insurance products available. Our professional staff strives to constantly exceed the service needs and expectations of our over 7,000 clients throughout the New England area.
Our History
Robert L. Halstead Sr. founded Halstead Insurance in 1966. As the family insurance business began to thrive, the agency's focus always remained the same. For over 45 years we have strived to build a full service agency that provides outstanding customer service while offering the best value in personal and commercial insurance products available to our customers. Current agency president Anthony P. Trapasso Jr., Robert’s son-in-law, joined the agency in 1987. The agencies focus was to continue to develop our Personal Lines and Commercial Lines business which would allow us to represent some of the leading insurance companies in the country. Michael Halstead, the agency's General manager, joined the team in 1991 and Kevin Halstead, our Commercial Sales manager, joined in 1993. Ann Marie Halstead Trapasso, our Financial manager, began working at the agency in 2001. The business has grown steadily due mainly to a strong dedication to its loyal customer base.
Today the Halstead Insurance Agency has grown to a staff of 15 dedicated employees which includes our second location, M. J. Flanagan Insurance Agency of Sterling, Ma. We welcome Paul and Michael Flanagan and their experienced staff to the Halstead Insurance Group. Together, we continue to be committed to providing our new and existing clients with outstanding customer service & value. We have carefully selected the insurance carriers that we represent, and our goal is always to meet the needs of our customers while helping them to maximize the value of their insurance investment. We are honored to be our clients personalized insurance advisors.





