If you are overwhelmed with Medicare options, we’re here to help with FREE, No-obligation assistance. 

About Us

For over three decades, we have guided our clients through the complexities of Medicare and have helped them make an informed decision about which option best suits their needs.   Whether you are just approaching eligibility for Medicare or are looking for an alternative to your current Medicare program, we welcome the opportunity to provide you with a free, no-obligation consultation to determine the right plan for you.  While we traditionally meet face-to-face with clients, we now offer our services through telephone or teleconference meetings.

Since 1989, The Cheshire Agency has been providing health insurance for Connecticut residents of all ages.  Offering just one product—health insurance—has allowed us to develop the expertise to determine our clients’ unique needs, research the market, and determine which policy best suits their needs.  MedicareOptions101 has further refined this specialization to assist our clients who are Medicare-eligible and want to understand all of their options.

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Finding The Perfect Plan

Step One:  We begin by getting to know what’s important to you when it comes to healthcare.   By understanding your unique needs, we can anticipate which plan will best suit your needs in the months to come.  We gather this information through a carefully designed questionnaire, which will help us to understand your usage of healthcare services.

Step Two:  Using this information, we go to work for you, free of charge.   We analyze every plan, from every major carrier in Connecticut, looking at their benefits, network, drug formulary, rates, and reputation.  By comparing this with how you use healthcare services, we can determine which plan best suits your needs.

Step Three:  We will explain your best options in a simple, concise way.   Sales material for all relevant plans is then reviewed to ensure a thorough understanding of any plans of interest.  If you decide to enroll, a short application is completed and forwarded to the insurance carrier for enrollment.

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Our Philosophy

Every policy we sell can be bought somewhere else for the exact same price, so why buy it from The Cheshire Agency?

We know that an insurance policy offers the most value only when you know how to use it.  For this reason, we make it our priority to ensure that every client understands their coverage, and how to access those benefits when they are needed.   We also understand that making a sale is just the beginning of providing  quality service.   Unlike some agencies which are happy to write the business and then provide you with a customer service phone number to the insurance company if you have a problem, we take an active role in assisting our clients with any issues they might encounter.   Whether it involves claims, billing, or simply requesting a new ID card, we are available all year long to ensure our clients’ experience is a smooth one.   And, because we are a local agency with ties to the local community, we thoroughly know the Connecticut market and understand what’s important to our clients.

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