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A private directory of licensed insurance agents. Not connected with or endorsed by Medicare or the U.S. government.

Cheshire County, New Hampshire

Medicare agents in Cheshire County, NH

Find a licensed agent with an office in Cheshire 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 Cheshire County

No agents with an office in Cheshire County are listed yet. Agents licensed anywhere in New Hampshire can help by phone or video: see agents in New Hampshire.

Before you meet anyone, check their New Hampshire license.

Medicare in Cheshire County

People with Medicare
21,939
In Medicare Advantage or another Medicare health plan
26% (5,634)
With both Medicare and Medicaid*
9% (2,007)

Cheshire County ranks 6th of New Hampshire's 10 counties by number of people with Medicare. 26% are in Medicare Advantage or another Medicare health plan, compared with 31% across New Hampshire. 9% also have Medicaid*, compared with 8% statewide.

Source: CMS Medicare Monthly Enrollment, July 2026, for the county and the state. Cheshire County has about 78,078 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 Cheshire County

Medicare Advantage with drug coverage
1 plan, 1 with a $0 plan premium
Medicare Advantage without drug coverage
0 plans
Special Needs Plans
1 plan: 1 for people who live in, or need the care of, a nursing home. Only people who qualify can join.
Companies offering these plans
2

For comparison, the typical New Hampshire county has 5 Medicare Advantage plans with drug coverage for 2027.

Standalone drug plans in New Hampshire: 8 plans, with monthly premiums from $5.30.

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 Cheshire County

Everything on this page applies across the whole county, including these places.

Cities and towns, largest first

  • Keene
  • Swanzey
  • Rindge
  • Jaffrey
  • Winchester
  • Hinsdale
  • Walpole
  • Chesterfield
  • Fitzwilliam
  • Troy
  • Marlborough
  • Alstead
  • Westmoreland
  • Dublin
  • Stoddard
  • Richmond
  • Harrisville
  • Surry
  • Gilsum
  • Marlow
  • Sullivan
  • Nelson
  • Roxbury

Unincorporated communities

  • North Walpole
  • West Swanzey

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

New Hampshire State Health Insurance Assistance Program (SHIP)
New Hampshire's free, unbiased Medicare counseling program. 1-866-634-9412 · Website
The New Hampshire Insurance Department
Licenses agents and takes complaints. 1-800-852-3416 · 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.

New Hampshire rules to know

Switching Medigap plans
New Hampshire 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. New Hampshire insurers must make every Medigap plan they sell available, at any age and with no health-based denial or pricing, to people who apply within 6 months of first enrolling in Part B, which includes people under 65 with a disability or kidney failure (ESRD).
Agent licenses
Agents must be licensed for health insurance in New Hampshire. 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 Cheshire 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 Cheshire County have Medicare?

In Cheshire County, 21,939 people had Medicare in July 2026, according to CMS. About 26% were in Medicare Advantage or another Medicare health plan; the rest had Original Medicare.

How many Medicare Advantage plans are offered in Cheshire County for 2027?

CMS lists 1 Medicare Advantage plans with drug coverage in Cheshire County for 2027 (1 with a $0 plan premium; you still pay the Part B premium), 0 without drug coverage, and 1 Special Needs Plans for people who qualify, from 2 companies. Medicare.gov's Plan Finder shows which ones cover your address, doctors and drugs.

Which towns does this page cover?

All of Cheshire County, including Keene, Swanzey, Rindge, Jaffrey, Winchester, Hinsdale, Walpole, Chesterfield and 17 more. Medicare Advantage plans are generally offered county by county, so the plan counts here apply across Cheshire County.

Which ZIP codes are in Cheshire County?

03431, 03441, 03443, 03444, 03445, 03446, 03447, 03448, 03450, 03451, 03452, 03455 and 13 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 Cheshire County?

New Hampshire's free counseling program, New Hampshire State Health Insurance Assistance Program (SHIP) (1-866-634-9412), 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.

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