To speak with a licensed insurance agent, call (774) 722-7687 (TTY 711, M-F 9am-5pm) or email kelley@kelleyhill.org
Kelley Hill

Your Guide to
Medicare Options

Information, Plan options,
and No-Cost Enrollment Assistance

Are You New To Medicare?

Not Sure Where to Begin?

As a new Medicare beneficiary, you have important decisions to make about the future of your healthcare.  Unfortunately, understanding the “ins-and-outs” and selecting the right plan based on your needs can be challenging.

Start by enrolling in our virtual course where you’ll learn the important basics and then for more in-depth information, read through the content of this site and connect with one of our licensed and certified agents in your local area for free assistance.

Begin by Enrolling in Our Medicare Essentials Video Quick-Course:

This video tutorial covers the basic elements of Medicare in a format that is easy to understand and you can watch it from the comfort of your home!  It’s yours at no cost and no obligation, just tell us where we should send it!


      By submitting this information, you acknowledge a licensed insurance agent, Kelley Hill, may contact you by phone, email, or mail to discuss Medicare Advantage Plans, Medicare Supplement Insurance, or Prescription Drug Plans.

      Get Free and Friendly
      Medicare Help Now

      Our licensed agents offer Medicare enrollment assistance
      at no cost and no obligation!


      Medicare Resources:
      What You Need to Know

      Important Information at Your Fingertips


      Getting Started

      Answers to common questions such as: When should you enroll?  How and when do you become eligible for Medicare?

      Enrollment Periods

      After your initial enrollment, Medicare allows you to make changes to your coverage at specific times each year. Here are those dates.

      Defining the ABC’s

      Medicare consists of Parts A, B, C, and D.   Step one is to learn the “ABC’s”, how they work, and your options with each part.

      Medicare Advantage Plans

      Medicare Advantage Plans are provided by private insurance companies and can often have lower out of pocket cost.

      Medicare Supplement Plans

      Insurance sold by private insurance companies to cover Medicare’s gaps.  Also called “MediGap” plans.

      Medicare Part D

      Medicare’s Part D is coverage for your medication needs and is provided by private insurance carriers. We’ll explain exactly how it works.

      Special Needs Plans

      SNPs are Advantage Plans that are tailored to meet the needs of individuals with certain health conditions or circumstances.

      Medicare FAQs

      Answers to some of the most common questions asked by Medicare beneficiaries.

      Frequently Asked Questions


      How do I apply for Medicare?

      How do I apply for a Medicare Advantage or Supplement Plan?

      Can I apply for Medicare in person?

      Can I get assistance applying for Medicare?

      When should I apply for Medicare?

      What if I missed my Initial Enrollment Period?

      Are there penalties for enrolling late?

      When do I get my Medicare card?

      Testimonials

      Here’s what our clients say about our service…


      I can’t express enough gratitude for the incredible support I received from Kelley Hill.

      Read More


      Marietta S.

      I can’t express enough gratitude for the incredible support I received from Kelley Hill.

      My sister has Alzheimer’s and I needed a great medical insurance that would cover her future needs, the paperwork and denials were overwhelming. Kelley went above and beyond to assist. She even drove all the way from the Cape to Central Massachusetts just to explain and assist with the paperwork and then connected me with a contact at MassHealth to ensure my sister was approved, even after we faced a denial due to being over income.

      Her knowledge of the Medicare process and her network of connections with other insurance programs are invaluable. Kelley was always true to her word, and following up within the time frame she promised.

      As my sister’s caretaker, this made a huge difference in reducing the stress I was feeling. I’m forever grateful for her compassion, dedication and her network of friends. It was the Right choice to call Kelley Hill.


      Marietta S.

      I had the pleasure of working with Kelley Hill for my Medicare needs, and I couldn’t be more satisfied with the experience. From our very first interaction, Kelley demonstrated a remarkable level of professionalism and expertise. She took the time to thoroughly explain my options, ensuring that I understood each detail clearly.

      Read More


      Alan R.

      I had the pleasure of working with Kelley Hill for my Medicare needs, and I couldn’t be more satisfied with the experience. From our very first interaction, Kelley demonstrated a remarkable level of professionalism and expertise. She took the time to thoroughly explain my options, ensuring that I understood each detail clearly.

      What truly set Kelley apart was her responsiveness. No matter how many questions I had or how often I reached out, she was always quick to provide answers and support. Her timely communication made the entire process smooth and stress-free.

      Kelley is incredibly knowledgeable about Medicare plans and policies, and her guidance was invaluable in helping me make the best decision for my needs. I highly recommend Kelley to anyone seeking reliable and expert advice on Medicare. Her dedication and expertise truly made a difference.


      Alan R.

      Articles and Information


      When Does It Make Sense to Switch Medicare Plans?

      Before making a switch during an eligible enrollment period, review your doctors, medications, travel needs, and long-term health outlook. Then, give us a call to discuss your options.

      Medicare for Snowbirds and Frequent Travelers: Think Before You Enroll

      Before enrolling in a Medicare plan, think about where you spend your time, which doctors you want to see, and how often you travel.

      Does Medicare Cover Long-Term Care?

      Many retirees are surprised to learn that Medicare does not fully cover long-term care. Understanding what is and isn’t covered can help you plan for potential future expenses and make important retirement planning decisions.

      Medicare Advantage Prior Authorizations: What You Need to Know

      If you are enrolled in a Medicare Advantage plan, you may have encountered the term prior authorization. While it may sound complicated, understanding how prior authorizations work is essential to avoiding unexpected delays or costs in your healthcare.

      What Happens to Your Medicare Plan If Your Health Changes Midyear?

      What happens if your health changes midyear? More to the point: What if your current Medicare plan isn’t the best fit for your needs now?

      What Medicare Doesn’t Cover and How People Are Filling the Gaps

      If you are unsure what your Medicare plan does or does not cover, now is a great time to review your options. Contact us today and connect with a licensed insurance agent.

      Medicare and Chronic Conditions: How Plans Can Impact Ongoing Care

      For individuals managing chronic conditions, choosing the right Medicare plan is especially important.

      Tips for Choosing a Medicare Plan with Your Doctors and Hospitals

      Choosing a Medicare plan is not just about monthly cost and coverage. One of the most important factors to consider is whether your preferred doctors and hospitals are included.

      Can AI Replace Human Licensed Insurance Brokers? Here’s What You Should Know

      AI can be a valuable tool for learning and exploring options, but it should not replace human guidance when making important healthcare decisions.

      Read Additional Articles

      Join Our Newsletter List

      Each month we deliver health tips straight to your email inbox. Try it, we think you’ll like it!

      You can unsubscribe at any time.


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