Meet Your Medicare Agent - Samuel Milewski

Licensed Health & Life Producer


Samuel Milewski is a family-first professional who brings empathy and care to every client interaction. Growing up with his parents, two sisters, and grandmother, he saw firsthand the impact Medicare can have on seniors—an experience that drives his commitment to helping others today. Samuel began his career in healthcare staffing before earning his Health and Life Insurance license and joining Medicare Joe, LLC.

Now, he spends his days educating seniors on Medicare, guiding them through enrollment and helping them understand their plan options. Outside of work, Sam enjoys playing guitar, golfing on the weekends, and cheering on the Worcester Red Sox.


I cannot express enough our gratitude to Medicare Joe in general and Michael DuRoss specifically. What a great service Medicare Joe is! At 64 and 4 months and with a younger husband, we had a LOT of very specific questions with various timelines, and Mike did a phenomenonal job helping us sort it all out. I recommend them with 10 stars, not 5!
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jeanie r. Avatar
jeanie r.
10/16/2026
Adam was very helpful & professional, answering all of my questions & promptly responded to questions sent by email. The videos are a great resource too!
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Andrea C. Avatar
Andrea C.
10/15/2026
I found this company through LinkedIn and signed up for one of their webinars. Great pitch, great values and my contact, Sarah has been great to work with. Very responsive, and knowledgeable about all the different options. Highly recommend.
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Gary F. Avatar
Gary F.
10/13/2026
Sarah was very knowledgeable about patient in finding what I believe to be the best plan for me. I just transitioned to Medicare and have yet to use it (which is why I gave 4 stars instead of 5). Hopefully, things will go smoothly. 😊
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Frances T. Avatar
Frances T.
10/08/2026
This whole process seemed very overwhelming, and I was so grateful to have Sam and his team by my side, every step of the way
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Jayne C. Avatar
Jayne C.
10/08/2026
Medicare Joe and his staff were great to work with for help navigating the Medicare process. Sarah Lopez answered all of my questions and walked me through each stage so that my husband and I are prepared with Medicare health insurance coverage that begins this month. I highly recommend!
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Hedda Avatar
Hedda
10/08/2026
I have had The Best experience from the start. The ad showed up on my Fb feed for an informational free Medicare webinar, and honestly, I was a bit skeptical. I decided to sign up as I am approaching retirement. The sign up was easy and they sent a couple appropriate reminders. The seminar was phenomenal. Very well presented, organized , and loaded with information. However, the follow-up was even better! My contact was Adam. He was very professional, knowledgeable, and kind. He took time to listen to my fears, concerns, and goals. He then gave options for my personal situation, and a time-line that has eased my anxiety. I have already, and will continue to recommend ❗️10/10 definitely.
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Robin K. Avatar
Robin K.
10/06/2026
Great advocates for people needing assistance understanding their Medicare choices.
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Sheila W. Avatar
Sheila W.
10/05/2026
I have had very positive experiences with Medicare Joe. The staff are very well informed and very knowledgeable about Medicare, the plans, the advantages and disadvantages, the costs. I felt like I could trust their information.
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Margie S. Avatar
Margie S.
10/05/2026
Sarah made this experience so much easier than we anticipated. She kept us on track and helped every step of the way. Thank you so much!
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Laura Z. Avatar
Laura Z.
10/05/2026
Austin was so helpful and patient with this unknowing lady about what I needed to do and not to do right now and what my best options were! I look forward to next year to talk to him again and see the new options with him thanks Austin!!
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KAREN L. Avatar
KAREN L.
10/05/2026
Very informative webinar. The representative I spoke with, Jeff, was knowledgeable and friendly. He made sure I understood what the process was and guided me through it. I was enrolled with what I needed in a quick session.
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NYAZ B. Avatar
NYAZ B.
10/05/2026
Very informative
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Mechelle S. Avatar
Mechelle S.
10/05/2026
Medicare Joe definitely prepared me for all of my Medicare questions, concerns and planning. Medicare can be very overwhelming and stressful for anyone turning 65 years old. It was very stressful for me because of the uncertainty and unknown with the all the information and mail I was receiving. Medicare Joe stepped in and relieved me of my stress and provided me with very valuable information. They managed the entire process for me and was there to answer my questions when needed.Christian Samuels was my agent who was very professional, patient and very knowledgeable.I highly recommend Medicare Joe to everyone!
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Wayne D. Avatar
Wayne D.
10/05/2026
Keila was so very helpful! I don’t believe I could have made it through the process without her. She explained all of the different parts so well. She made the whole process extremely easy. I recommend Medicare Joe to everyone!!
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Kay R. Avatar
Kay R.
10/03/2026
They made it so easy for me to get on Medicare. I'm turning 65 Oct.7th and they had everything ready for me starting on the 1st. I just lost my husband last yr. and had no idea what to do and they did it all for me. Quick, easy and painless. Thanks Medicare Joe.
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dana d. Avatar
dana d.
10/02/2026
I would totally be lost without Christian Samuels assistance.
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Carmen M. Avatar
Carmen M.
10/02/2026
We have been dealing with Medicare Joe people for at least three years now. Mark always finds what we need as far as our Medicare policies. Any riders that we need. He always has a good head on his shoulders to look out for the unexpected that may turn up as we get older. Appreciate all they’ve done for us.
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deb g. Avatar
deb g.
10/02/2026
Keila responded promptly to my emails and took the time to explain things in a manner that I could understand. She was very pleasant and and made sure I understood my options to make an informed decision!
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Bridgette T. Avatar
Bridgette T.
10/02/2026
I was stressing so much about signing up for medicare but Jeffrey made the entire process stress free! I am so glad i made the call! With Jeffrey’s guidance i am all set! Thanks again for making my switch to Medicare so smooth!!!
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Patricia O. Avatar
Patricia O.
10/02/2026
Medicare Joe is a lifesaver! I was amazed, upon turning 65, at how complicated Medicare can be! Suddenly, I was getting hundreds of emails, texts, and phone calls literally from folks trying to sell me their plan. It was overwhelming. Then I watched a Medicare Joe video and thought these guys could really help me. As a person who made their career in hospitality, I was impressed by the service, the expertise, and the kindness in their service. Devon now has me on the right track with a plan that fits my needs and I can finally relax and enjoy life again. I cannot recommend Medicare Joe enough!
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John M. Avatar
John M.
10/02/2026
Medicare Joe helped me so much. I watched the webinar. Took lots of notes for when I had my one on one personal call. They explained everything, answered all my questions and helped me make the best choice for me. I also love how its not a one and done that they stay with you and will be there every year to reevaluate your changing needs and educate you on your options. All I can say is thank you 💞
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Judy B. Avatar
Judy B.
10/02/2026
I am not comfortable with online advertisements. So, initially I was apprehensive but I am so glad I followed through. The experience has been great! When I call I get a call back and the customer service is also great. Made my signing up process so much easier than I anticipated. Thank you.
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Phyllis R. Avatar
Phyllis R.
9/27/2026
Excellent care. Mark had gone over everything, help with picking out a plan that suits me. Helped fill out all the paperwork so I didn't need to do anything. I have recommended him and the company to a few people.
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Lori S. Avatar
Lori S.
9/17/2026
Thank you for all the help. You made the whole process very easy
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Jack L. Avatar
Jack L.
9/11/2026
Christian made this process easy to understand and implement. Thank you so much Christian and Medicare Joe for clear and easy to understand educational videos!
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Donna D. Avatar
Donna D.
9/11/2026
I had the Most wonderful experience with Medicare Joe! Specifically it was Jeffrey Alves, who gave me the time, the attention, The explanations and the unlimited patience to walk me through making the best possible choices for me. I was not a cookie cutter client! His personal attention To me specifically and what the best options would be the right ones for me personally was amazing. He followed through with me several times, made going through the process so very easy and was always just a phone call away. I could not recommend this company and Jeff more. So if you’re looking for assistance with the seemingly Unlimited choices and navigating a system that can often times be frustrating and full of unknown, this is the place to go! Thank you, Medicare Joe!
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Lisa J. Avatar
Lisa J.
9/11/2026
My Agent has been Extremely Knowledgeable,Helpful, Friendly, Communicative, Comforting & Available at all times.His follow-up and alerts have been Awesome!I have been very happy throughout the Process.
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Michael H. Avatar
Michael H.
9/10/2026
Jeffrey was very professional and thorough. He explained what I needed and sent me links to forms needed to be completed.
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David G. Avatar
David G.
9/10/2026
My agent with Medicare Joe explained everything to me and walked me through the process of getting signed up with Medicare on time. He was always available to answer questions and to help me make choices I felt comfortable with. I’m so thankful I had someone to help me find my way through the whole process at this time in my life.
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R L. Avatar
R L.
9/10/2026
Medicare Joe assisted Getting me started with medicare that was needed/required. It eased the burden of me trying to figure things out and making a guess on what I should and should not do. When I had questions, I got immediate response. I have referred him to people who is approaching the mandatory Medicare submission age.
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Michael B. Avatar
Michael B.
9/10/2026
Christian Samuels was very helpful and stuck it through me the whole time.
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Lisa V. Avatar
Lisa V.
9/10/2026
Well educated, very knowledgeable
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Angel M. Avatar
Angel M.
9/10/2026
Answers and advice was professional and delivered with expertise and kindness. Sometimes choices/scenarios had to be qualified and explained to me more than once, which as I said was done with a positive and professional responses.Highly recommend this company!
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Gabrielle S. Avatar
Gabrielle S.
9/09/2026
Medicare Joe was very professional in helping and guiding me through the process of selecting the best and most affordable Medicare plan for my needs. They were always responsive when I had questions and followed up with me along the way of applying for Medicare. I would highly recommend using this agency.
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Kathleen A. Avatar
Kathleen A.
9/09/2026
Medicare Joe has a fabulous team. They kept me on track each and every step of the way to get my Medicare complete. I am so happy I had them to help me.
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Sharilyn C. Avatar
Sharilyn C.
9/09/2026
Austin was quick and efficient while signing up for Medicare for the first time. It went smoothly and was seamless. I was appreciative. Additionally, when I later had questions he was really quick to answer, so I knew I had made the right choice going with Medicare Joe.
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Kathy C. Avatar
Kathy C.
9/09/2026
Devon at Medicare Joe was great! My situation is a bit unique in that at 65, I still have 3 dependent children who are in need of staying on my health insurance plan. He helped me with the insurance and outs of maintaining that plan and deciding if getting medicare for me at this time made sense. While medicare seems simple at the outset . . . the deeper I dove it became more complicated. Devon's knowledge was so helpful!I feel confident that I ended up in the right place! Thanks!!!
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Christy G. Avatar
Christy G.
9/08/2026
The best. Explained my options in relatable and easy to understand terms. Followed up when I was told they would. Excellent service!
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tdl914 Avatar
tdl914
9/08/2026
They have helped with every need!!
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kathiem777 Avatar
kathiem777
9/08/2026
Very helpful and knowable.Great with a fast response to any questions I had .
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Gigi L. Avatar
Gigi L.
9/08/2026
Austin was very helpful, helping me find the best Medicare plan for me. He was so patient with me and answered all my questions! He really relieved the stress of finding the right plan for me! Thanks MedicareJoe.
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Lorie K. Avatar
Lorie K.
9/08/2026
Austin took care of the Medicare transition seamlessly! Thank you for being there to assist! It’s an ocean of information to take in. Your help was appreciated very much !
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Belinda W. Avatar
Belinda W.
9/08/2026
I had great pleasure working Christopher C. Medicare can be complex. I'm so appreciative for his support. He's very patient, informative and an amazing fun guy to talk with. With his knowledge, I felt I made the right choices. Thank you so much ...
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Lana G. Avatar
Lana G.
9/07/2026
I thoroughly enjoyed talking to the rep assigned to my case. He was very knowledgeable and gave me multiple options.
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Danelle W. Avatar
Danelle W.
9/07/2026

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