TSM Life & Health is an independent, licensed agency helping Massachusetts residents compare Medicare Advantage, Medicare Supplement, Part D, life insurance, final expense and annuity options in plain language. For 2026, CMS lists 28 Medicare Advantage (MA-PD) plans in Middlesex County, 30 in Suffolk County (Boston) and 36 in Worcester County, many at a $0 monthly plan premium. For individual and family health plans, Massachusetts runs its own exchange — the Massachusetts Health Connector — not the federal Marketplace. We help you compare, at no cost and no pressure.
County-level snapshots we pulled live from the CMS Medicare Advantage / Part D Landscape for contract year 2026. Medicare Advantage availability is set county by county, so the figures below are three major-county examples within Massachusetts, not statewide totals.
Every figure below is for Medicare Advantage plans with prescription drug coverage (MA-PD) in the named county for contract year 2026. Averages are computed across all MA-PD plans CMS lists in that county. Middlesex County uses ZIP 02139 (Cambridge), Suffolk County uses ZIP 02108 (Boston) and Worcester County uses ZIP 01608 (Worcester) as representative anchors within Massachusetts.
| County (metro) | MA-PD plans | $0-premium plans | Avg premium/mo | Avg in-network MOOP | Avg Part D deductible | Plans rated 4★+ |
|---|---|---|---|---|---|---|
| Middlesex (Cambridge) | 28 | 11 | $86.29 | $5,300 | $310 | 19 of 25 rated (76%) |
| Suffolk (Boston) | 30 | 13 | $84.20 | $5,357 | $299 | 18 of 27 rated (67%) |
| Worcester | 36 | 19 | $65.22 | $5,546 | $314 | 24 of 33 rated (73%) |
A $0 plan premium does not mean $0 cost — you still pay your Medicare Part B premium and any plan copays or coinsurance. The in-network maximum out-of-pocket (MOOP) is the most you would pay for covered Part A and Part B services in a year; once you reach it, the plan pays 100% for the rest of the year. Star-rating counts are out of the plans CMS has rated in each county; some newer plans are not yet rated.
Unlike most states, Massachusetts does not use the federal HealthCare.gov Marketplace. The Commonwealth runs its own exchange, the Massachusetts Health Connector, where residents shop for individual and family (non-group) health and dental plans, apply for MassHealth, and find out whether they qualify for state and federal financial help such as ConnectorCare and premium tax credits. Because plan listings, subsidies and enrollment dates for these plans are managed by the Health Connector, we point you there for current individual-market quotes and eligibility.
Enroll or compare individual and family plans directly at the Massachusetts Health Connector (mahealthconnector.org). Open Enrollment for a new plan year runs in the fall and winter, and a qualifying life event can open a Special Enrollment Period at other times — check the Health Connector for the exact dates that apply to you. If you are turning 65 or already on Medicare, that is a separate program, and we can help you compare your Medicare options directly.
TSM Life & Health is an independent, licensed insurance agency (founder Keith McLiverty, National Producer Number 3481853). We are licensed in Massachusetts and work with Massachusetts residents by phone and video, so you get the same plain-spoken, no-pressure guidance whether you are in Boston, Cambridge, Worcester, Springfield or anywhere else in the Commonwealth. Because we are independent, we help you compare options across carriers — we do not work for any one insurance company.
Yes. We are an independent, licensed insurance agency serving Massachusetts residents. We help you compare Medicare Advantage, Medicare Supplement, Part D, life insurance, final expense and annuity options by phone and video, at no cost to you.
Availability is set county by county. For 2026, CMS lists 28 MA-PD plans in Middlesex County, 30 in Suffolk County (Boston) and 36 in Worcester County, with many offering a $0 monthly plan premium. Tell us your county and we will pull the current list for you.
Massachusetts runs its own exchange — the Massachusetts Health Connector — instead of the federal HealthCare.gov Marketplace. You shop for individual and family plans and check for financial help such as ConnectorCare at mahealthconnector.org. Medicare is a separate program, and we can help you compare your Medicare options directly.
Medicare has an Annual Enrollment Period from October 15 to December 7 each year, plus Initial and Special Enrollment Periods tied to turning 65 or certain life changes. For individual health plans through the Massachusetts Health Connector, Open Enrollment runs in the fall and winter — check the Health Connector for exact dates. We can help you find the window that applies to you.
No. There is no cost to you to compare plans with us. We are compensated by the carriers when you enroll, and we present your options neutrally so you can choose what fits.
Sources. Medicare Advantage plan counts, $0-premium plan counts, average monthly consolidated (Part C+D) premiums, in-network out-of-pocket maximums, Part D deductibles and CMS Overall Star Ratings come from the CMS Medicare Advantage / Part D Landscape for contract year 2026 (cms.gov), for Middlesex, Suffolk and Worcester counties, MA, covering MA-PD plans; averages are computed across the plans in each county and star-rating counts exclude plans CMS has not yet rated. Massachusetts operates its own health insurance exchange, so individual and family ACA plan listings and subsidies come from the Massachusetts Health Connector (mahealthconnector.org), not the federal HealthCare.gov Marketplace. Data accessed via The Brain (Ambrose) MCP on July 31, 2026. For all of your Medicare options, see medicare.gov or ssa.gov.
TSM Life & Health is an independent, licensed insurance agency. We do not offer every plan available in your area. Any information we provide is limited to the plans we do offer in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your State Health Insurance Assistance Program (SHIP) to get information on all of your options. We are not connected with or endorsed by the U.S. government, the federal Medicare program, or CMS. Figures are estimates for education only, not quotes or guarantees of coverage or savings. Verify current plan details with a licensed agent before enrolling.
Most Massachusetts residents choose one of three paths when they become eligible for Medicare. Here is how they compare in plain language. We are an independent agency and we do not offer every plan available in your area — we help you weigh the options neutrally.
| Path | What it is | Good to know |
|---|---|---|
| Original Medicare | Federal Part A (hospital) + Part B (medical). Covers the essentials of inpatient and outpatient care. | Does not include built-in drug coverage or a yearly out-of-pocket cap. Many pair it with a Part D drug plan and a Medigap (Supplement) policy. |
| Medicare Advantage (Part C) | A private plan that bundles Part A and Part B, and usually Part D, into one plan — often with extra benefits. | Typically includes a yearly out-of-pocket maximum and uses a provider network. Benefits and networks vary by plan and county. |
| Medicare Part D | Prescription drug coverage from private plans. | Can pair with Original Medicare as a stand-alone plan, or come built into a Medicare Advantage plan. |
Timing matters. These are the standard Medicare enrollment windows set by CMS.
| Enrollment period | When | What it is for |
|---|---|---|
| Initial Enrollment Period (IEP) | The 7 months around your 65th birthday — the 3 months before, your birthday month, and the 3 months after. | Your first chance to enroll in Medicare when you turn 65. |
| General Enrollment Period (GEP) | January 1 – March 31. | For those who missed their IEP; coverage starts the month after you sign up. |
| Annual Enrollment Period (AEP) | October 15 – December 7. | Add, drop or switch Medicare Advantage and Part D plans for the coming year. |
| Medicare Advantage Open Enrollment | January 1 – March 31. | If you are already in a Medicare Advantage plan, you can switch once or return to Original Medicare. |
A Special Enrollment Period can also open after a qualifying event, such as losing employer coverage or moving out of your plan’s service area.
You are generally eligible for Medicare if any of the following apply:
Statewide figures we pulled from live federal data: the CMS Medicare Advantage / Part D Landscape for contract year 2026 and the CMS Medicare Monthly Enrollment file. Unlike the county tables above, these are Massachusetts totals.
Sources: CMS Medicare Advantage / Part D Landscape, CY2026, and CMS Medicare Monthly Enrollment (2025 annual), via data.cms.gov · accessed 2026-07-31. A $0 plan premium does not mean $0 cost — you still pay your Part B premium and any copays. We do not offer every plan available in your area.
No pressure — just a clear path. Here is how we help Massachusetts residents get to a confident decision:
These free, official resources can help you compare and understand your options. SHINE is Massachusetts’s State Health Insurance Assistance Program (SHIP), which offers free, unbiased Medicare counseling.
Medicare is usually the reason people call, but it’s rarely the only thing on the kitchen table. We’re an independent agency, so we compare across carriers rather than representing one — and a fair number of these conversations end with us telling someone that what they already have is the right fit.
Not sure which of these applies to you? That’s a normal place to start. Book a free consultation or call 203-951-0339 and ask one question — that is allowed.
You will probably recognize yourself in one of these. Each one starts in a different place, so each one gets a different first conversation.
There are three shopping bags of mail on the table, every plan claims to be free, and you’d like to keep your cardiologist. We start with your doctors and your prescriptions, then look at the plans — not the other way around.
Start with MedicareYou’re the one reading small print at 11pm, wondering whether the postcard that looks like a Medicare card is a scam. Bring us the mail. We’ll tell you what’s real, and you can put us on speakerphone with your mother.
See how we workCOBRA quoted more than the mortgage payment and you’ve got a few years to get to Medicare. We help you think through the income estimate the Marketplace runs on, and set the calendar so you land on Medicare at 65 without a gap or a penalty.
Read the ACA guideSize it before you shop it — debt, income to replace, mortgage, education, minus what you already have. Then match the tool: term for the years with a mortgage and children in the house, a smaller permanent policy for what never expires.
See life insuranceNone of these are dramatic enough to notice in the mail. All three show up later — at the pharmacy counter, at the front desk, or in a monthly check that can’t be changed.
Working past 65 does not always let you delay Medicare. Whether you can wait depends on the size of your employer and whether the coverage counts as creditable. Nothing that arrives in the mail tells you which case you’re in, and the penalties for guessing wrong are added to your premium for as long as you hold the coverage. Here is how the enrollment windows actually work.
The higher earner’s Social Security decision is really the survivor’s decision. When one spouse dies, the survivor keeps the larger of the two checks — not both. So the higher earner’s claiming age sets the income the widow or widower lives on, potentially for decades. It’s the single most expensive thing to get wrong, and the easiest to miss. We walk through 62 versus 67 versus 70 here.
“Keep what I have” is one of the options being compared, not the default. Plans change every year — premiums, formularies, networks, the out-of-pocket maximum — and so does your life. Once a year we re-run your drug list and your doctors against the plans we offer in your area. If the plan you have is still the right one, that’s what we tell you, and it costs nothing either way. That yearly review is the part of the relationship that matters most.
Happy to look at any of this with you, at your pace. Our office is at 479 New Haven Avenue in Milford, Connecticut, and a real person answers the phone Monday to Friday 9–6 and Saturday 10–2. Get in touch.
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE, or your local State Health Insurance Assistance Program (SHIP), to get information on all of your options. TSM Life & Health is a licensed independent insurance agency and is not connected with, affiliated with, or endorsed by the U.S. government, the federal Medicare program, the Social Security Administration, or the Centers for Medicare & Medicaid Services (CMS). This is a solicitation for insurance; a licensed insurance agent may contact you. Product availability and benefits vary by state and carrier, and all guarantees are backed solely by the claims-paying ability of the issuing insurance company. This page is general educational information only and is not insurance, tax, legal, or investment advice.
Tell us your county, your doctors and your prescriptions, and we will help you match a plan — at no cost and no pressure.