Welcome to the John A. Pierce Insurance Agency, Inc.

 We are an independent insurance agency located in Winchester, Massachusetts offering auto, homeowners, life, and business insurance. We use top regional and national carriers to find the insurance policy that best fits your unique needs. We pride ourselves on our long-term commitment to making sure our clients have reliable and affordable coverage.

Established in 1923, the agency remains in Pierce-family hands, and is currently operated by the third-generation members Kevin Pierce, Carole Pierce Connolly, and Linda Pierce Tedesco. Among our clients are the family members of some of our grandfather’s and father’s clients. We encourage you to build a relationship with our family, and to allow us to develop an insurance program for your family and for your business.






Own bakery. Couple of successful businessman working hard in their own bakery in the morning


Life Insurance

Our Affiliations

Trusted Choice


What Our Clients Are Saying

Great service from a family run business! Been there for many years and have always had good experiences.”

Bob G.

Carole Connolly Pierce is fantastic.  I had a claim and she took care of it from beginning to end, making the necessary calls, doing the paperwork, and giving me excellent advice.  I never knew an insurance agent could do this much for a client.  I highly recommend Carole and this agency.

Kathryn R.

Excellent customer service! Linda was great with getting me an excellent quote and it took no time at all! I will definitely be a long time client of John Pierce Insurance.

Lane S.

Insurance Agent Rhode Island

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John A. Pierce Insurance Agency, Inc.

Hours of Operation

  • Monday-Thursday: 9:00am - 4:30pm
  • Friday: 9:00am - 4:00pm
  • Other hours by appointment

We are licensed in the states of Massachusetts, New Hampshire, Vermont, Rhode Island, Maine, and Florida.