Windsor County, Vermont
Medicare agents in Windsor County, VT
Find a licensed agent with an office in Windsor County, and see what Medicare looks like here: how many people have it, how many are in Medicare Advantage, and how many plans are offered for 2027.
Last reviewed October 27, 2026. General information, not advice about any plan.
Agents in Windsor County
No agents with an office in Windsor County are listed yet. Agents licensed anywhere in Vermont can help by phone or video: see agents in Vermont.
Before you meet anyone, check their Vermont license.
Medicare in Windsor County
- People with Medicare
- 17,465
- In Medicare Advantage or another Medicare health plan
- 15% (2,564)
- With both Medicare and Medicaid*
- 16% (2,796)
Windsor County ranks 3rd of Vermont's 14 counties by number of people with Medicare. 15% are in Medicare Advantage or another Medicare health plan, compared with 13% across Vermont. 16% also have Medicaid*, compared with 19% statewide.
Source: CMS Medicare Monthly Enrollment, July 2026, for the county and the state. Windsor County has about 57,697 residents (Census, 2024). Medicare health plans include Medicare Advantage, cost plans and PACE, not Medigap or drug plans. *Includes people who get help only with Medicare costs from a Medicare Savings Program.
2027 plans offered in Windsor County
- Medicare Advantage with drug coverage
- 3 plans, 1 with a $0 plan premium
- Medicare Advantage without drug coverage
- 1 plan
- Special Needs Plans
- 0 plans. Only people who qualify can join.
- Companies offering these plans
- 1
For comparison, the typical Vermont county has 0 Medicare Advantage plans with drug coverage for 2027.
Standalone drug plans in Vermont: 10 plans, with monthly premiums from $13.30.
Source: CMS 2027 plan landscape (updated October 2026), which lists plans by county. A $0 plan premium doesn't mean $0 costs: you still pay the Part B premium, plus copays, and plans differ in their yearly limit and in which doctors and drugs they cover. How to compare.
Cities, towns and ZIP codes in Windsor County
Everything on this page applies across the whole county, including these places.
Cities and towns, largest first
- Hartford
- Springfield
- Norwich
- Windsor
- Hartland
- Woodstock
- Chester
- Weathersfield
- Royalton
- Ludlow
- Bethel
- Sharon
- Cavendish
- West Windsor
- Rochester
- Barnard
- Pomfret
- Bridgewater
- Stockbridge
- Reading
- Plymouth
- Weston
- Andover
- Baltimore
Unincorporated communities
- Ascutney
- Hartford Village
- North Hartland
- North Springfield
- Proctorsville
- Quechee
- South Royalton
- South Woodstock
- West Woodstock
- White River Junction
- Wilder
ZIP codes
Source: Census Bureau, Vintage 2024 population estimates, the 2020 list of census-designated places, and 2020 ZIP Code Tabulation Areas (which leave out ZIP codes used only for PO boxes). A place or ZIP code that crosses a county line is listed in each county it covers a real part of.
Free local help
- State Health Insurance Program (SHIP)
- Vermont's free, unbiased Medicare counseling program. 1-800-642-5119 · Website
- The Vermont Department of Financial Regulation
- Licenses agents and takes complaints. 1-800-964-1784 · How to check a license
- 1-800-MEDICARE
- 1-800-633-4227 (TTY 1-877-486-2048), 24 hours a day, 7 days a week, except some federal holidays.
Vermont rules to know
- Switching Medigap plans
- Vermont doesn't add a yearly Medigap switching right. Outside your 6-month Medigap Open Enrollment Period (which starts when you're 65 or older and have Part B) and certain federal protections, such as losing other coverage, insurers can usually ask health questions and turn you down. States with switching rights.
- Medigap under 65
- Required, with limits. If you get Medicare because of a disability, insurers must offer you the same Medigap policies they sell to people 65+, with at least a 6-month enrollment window after you become eligible; this does not apply to people who qualify only because of kidney failure (ESRD).
- Agent licenses
- Agents must be licensed for health insurance in Vermont. Look one up.
Dates to know
- October 15 to December 7
- Open Enrollment: change Medicare Advantage or drug plans for the next year.
- January 1 to March 31
- Medicare Advantage Open Enrollment: one change for people already in a Medicare Advantage plan.
- Turning 65
- A 7-month window around your birthday month. The checklist.
Moving to Windsor County from another state opens a special enrollment period for Medicare Advantage and drug plans. It doesn't by itself let you buy Medigap without health questions. What to do.
Common questions
How many people in Windsor County have Medicare?
In Windsor County, 17,465 people had Medicare in July 2026, according to CMS. About 15% were in Medicare Advantage or another Medicare health plan; the rest had Original Medicare.
How many Medicare Advantage plans are offered in Windsor County for 2027?
CMS lists 3 Medicare Advantage plans with drug coverage in Windsor County for 2027 (1 with a $0 plan premium; you still pay the Part B premium), 1 without drug coverage, and 0 Special Needs Plans for people who qualify, from 1 companies. Medicare.gov's Plan Finder shows which ones cover your address, doctors and drugs.
Which towns does this page cover?
All of Windsor County, including Hartford, Springfield, Norwich, Windsor, Hartland, Woodstock, Chester, Weathersfield and 27 more. Medicare Advantage plans are generally offered county by county, so the plan counts here apply across Windsor County.
Which ZIP codes are in Windsor County?
05001, 05009, 05030, 05031, 05032, 05034, 05035, 05037, 05048, 05052, 05053, 05055 and 24 more, according to the Census Bureau. A ZIP code that crosses a county line can be listed in more than one county.
Where can I get free Medicare help in Windsor County?
Vermont's free counseling program, State Health Insurance Program (SHIP) (1-800-642-5119), gives unbiased one-on-one help. You can also call 1-800-MEDICARE (1-800-633-4227) any time.
Will I pay more for a plan if I use an agent?
No. A plan's premium is set by the plan, and you pay the same whether you enroll through an agent, the plan, or Medicare.gov. Agents can't charge a fee to enroll you in a Medicare Advantage or drug plan.
Nearby
Keep reading
- How to find a good Medicare agent near youWhere to look for a local Medicare agent, how to narrow the list to one or two, and the five-minute checks to do before you share anything.
- Medicare Open Enrollment checklist: what to check before December 7A step-by-step checklist for the October 15 to December 7, 2026 Open Enrollment Period: what to read in your plan's letter, what's changing for 2027, what you can switch, and what happens if you do nothing.
- Medicare Advantage or Medigap? The questions that decide itNeither is better for everyone. How the two common Medicare set-ups differ, the questions that point to one or the other, and why the first choice is the hardest to undo.
Ready to talk to someone local?
Search by ZIP code. Verified agents are listed first, and every listing is free to contact.