Winnebago County · Wisconsin
Medicare and retirement planning in Oshkosh, WI
Oshkosh anchors the southern half of Winnebago County, where roughly 71% of Medicare beneficiaries are enrolled in Advantage plans.
What's different here
The local picture
Oshkosh sits far enough south of the Fox Cities that referral patterns can pull toward Fond du Lac or Milwaukee for certain specialties. If you already see a specialist outside the immediate area, that relationship is the first thing to check against a plan's network — not the last.
Oshkosh sits in Winnebago County, and county is the unit that governs Medicare plan availability. Winnebago County sits on both sides of Lake Winnebago's western shore and covers two distinct markets — Oshkosh in the south and the Neenah–Menasha area in the north. About 71% of beneficiaries here are in Advantage plans.
Because Wisconsin is a Medigap waiver state, a quote you find on a national website is often for a plan that is not sold here at all. The comparison that matters in Wisconsin is which riders you add to the basic policy — not which letter you pick.
Winnebago County by the numbers
- Oshkosh population
- 67,242
- County population
- 173,307
- Residents aged 65+
- 31,772 (18.3%)
- People on Medicare
- 37,481
- In Medicare Advantage
- 26,632 (71.1%)
- On Original Medicare
- 10,849 (28.9%)
- Standalone Part D plans
- 7,650
- Medicare & Medicaid (dual)
- 4,649
How neighbours are covered
Winnebago County coverage mix
This is not a recommendation — plenty of people are in the minority column for very good reasons. It is context for the conversation.
| Category | Value |
|---|---|
| Medicare Advantage | 26,632 (71.1%) |
| Original Medicare | 10,849 (28.9%) |
| Standalone Part D | 7,650 |
| Drug coverage via Advantage | 24,801 |
| Also on Medicaid | 4,649 |
Categories overlap on purpose — someone in an Advantage plan with drug coverage appears in both the Advantage row and the drug-coverage row.
Available in Oshkosh
What we can help with locally
Nearby
Also serving
Communities around Oshkosh in Winnebago County and the surrounding area.
- Neenah
- Omro
- Winneconne
- Fond du Lac
- Ripon
All Wisconsin locations · Winnebago County overview · Every area we serve
Questions
Oshkosh questions
Which Medicare plans are available in Oshkosh?
Plan availability is set at the county level, so Oshkosh residents shop the Winnebago County plan menu. That menu changes every year, and we do not offer every plan available in the area — for a complete list, contact Medicare.gov, call 1-800-MEDICARE, or reach your State Health Insurance Assistance Program.
How many people in Winnebago County are on Medicare?
About 37,481 as of the CY2025 CMS enrollment data — 26,632 of them (71.1%) in Medicare Advantage plans and 10,849 (28.9%) on Original Medicare.
Do you charge for a review in Oshkosh?
No. There is no fee to review your coverage or compare options. Agent compensation is paid by the insurance carrier when a policy is placed, and it does not change what you pay in premium.
When can I change my Medicare plan?
Medicare Advantage and Part D changes are made during Annual Enrollment — October 15, 2026 through December 7, 2026, effective January 1, 2027. Certain life events, including moving out of your plan's service area or qualifying for Extra Help, can open a Special Enrollment Period at other times of year.
Do you meet in person in Oshkosh?
We are remote-first, so nearly every review — including in Oshkosh — happens by phone or video. In-person appointments are reserved for people who genuinely need one, in our northeast Wisconsin home area, and are assessed case by case when you book. Call (920) 455-5547 or book a time online and we will sort out the format.
Enrollment and population figures on this page describe the local market. They are not a statement about which plan is right for you, and they are not a quote. Plan availability, benefits and premiums vary by county, carrier and individual eligibility, and change every plan year.
Get a straight answer about your Oshkosh options
We will look at what you have now against what is actually available in Winnebago County this plan year, and tell you plainly whether a change is worth making.