Medicare 2026
Waukesha Medicare Support Through SHIP and Licensed Agencies
WAUKESHA, Wis. — If Medicare feels like a maze, you are not alone. With more than 84,000 residents age 65 or older in Waukesha County, thousands of neighbors are working through the same questions every year: What does Part D cover? Should I stay with Original Medicare? When can I switch?
Compare Medicare options near you
Answer 3 quick questions to see Medicare listings from licensed insurance partners.
What’s your ZIP code?
Plan availability is set by your county, so we start here.
How old are you?
This helps match you with options you’re eligible for.
Do you have Medicare Parts A & B?
This affects which Medicare options you can choose.
These listings are provided by licensed insurance partners.
Medicare Advantage plans in your area are changing or leaving for 2027.
One call tells you whether your plan is on the list — before enrollment opens.
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Continue →Advertising disclosure: MyMedicarePlans.org may be compensated when you contact a partner or licensed agent. Listings are not ranked or endorsed by us, and we do not recommend specific plans. You can also contact Medicare.gov, 1-800-MEDICARE, or your local SHIP.
Speak to a Licensed Insurance Agent
Click to call 855-729-3240Found a plan you like online?
One free call confirms it's actually right for you — online directories are wrong more often than you'd think.
- Your doctors — confirmed in-network for 2027
- Your prescriptions — checked against the plan's 2027 drug tiers
855-729-3240 · free · about 5 minutes
Key takeaways
- Waukesha County has more than 84,000 residents age 65 or older who face the same Medicare questions each year.
- Wisconsin's SHIP program, called the Medigap Helpline, offers free counseling with no sales pitch, since counselors don't sell insurance or earn commissions.
- In 2026, Waukesha County residents could choose from 57 Medicare Advantage plans offered by 9 carriers, according to CMS Landscape data. The 2027 lineup appears in each plan's ANOC and on Medicare.gov's Plan Finder.
- Missing your enrollment window may mean waiting a year to sign up, unless you qualify for a Special Enrollment Period due to a move, job change, or loss of coverage.
Free, unbiased Medicare help is closer than you think
The good news is that Waukesha has trained, unbiased help available at no cost — and you don't have to sit through a sales pitch to get it.
Start with SHIP — Wisconsin's free counseling service
Every state has a State Health Insurance Assistance Program (SHIP). It's federally funded, and its counselors do not sell insurance or earn commissions. Their job is simply to help you understand your options.
In Wisconsin, SHIP is called the Medigap Helpline, run by the Wisconsin Board on Aging and Long Term Care. Counselors can help you:
- Compare Medicare Advantage, Medigap, and Part D options
- Understand what a plan actually covers before you enroll
- Check whether you qualify for programs that help pay premiums or drug costs
- Sort out billing problems or claim denials
Wisconsin Medigap Helpline: 1-800-242-1060 (weekdays) Wisconsin Medigap Part D and Prescription Drug Helpline: 1-855-677-2783
Local help right here in Waukesha County
The Waukesha County Aging and Disability Resource Center (ADRC) is another trusted local resource. ADRC staff and volunteers can walk you through Medicare basics, help you use the Plan Finder on Medicare.gov, and connect you with benefits programs.
Waukesha County ADRC: 262-548-7848 Location: Health and Human Services Center, 514 Riverview Ave., Waukesha
Because ADRC counselors are not tied to any insurance company, they can give you a straight answer about what fits your situation — even if the answer is "keep what you have."
When a licensed agent makes sense
SHIP and ADRC counselors are terrific for education and comparisons, but they cannot enroll you in a plan. That's where a licensed independent insurance agent comes in.
A few tips if you go this route:
- Ask which carriers they represent. An independent agent who works with multiple carriers can show you a wider range of options than a captive agent tied to one company.
- Ask how they are paid. Agents are paid by the insurance company, not by you — but you deserve to know that up front.
- You are never required to enroll on the spot. A good agent will let you take notes home and think it over.
According to CMS Landscape data, Waukesha County residents had 57 Medicare Advantage plans available through 9 carriers offering MA-PD coverage in 2026. The 2027 lineup is detailed in each plan's Annual Notice of Change and on Medicare.gov's Plan Finder. That's a lot to sort through, which is why so many people find it helpful to talk with someone before choosing.
Key numbers worth knowing
Whether you meet with SHIP, ADRC, or an agent, these program-level figures apply to everyone on Medicare:
- Part D out-of-pocket cap: $2,100 in 2026 and $2,400 in 2027 — once you hit that, you pay nothing for covered drugs the rest of the year.
- Part D maximum deductible: $615 in 2026 and $700 in 2027.
- Coverage gap ("donut hole"): eliminated as of 2025.
- Medicare Prescription Payment Plan: lets you spread drug costs into level monthly payments instead of paying big bills at the pharmacy counter.
- IRMAA surcharges: kick in above $109,000 in income for a single filer in 2026.
Mark these enrollment windows
- Annual Enrollment Period: Oct. 15 – Dec. 7 (changes take effect Jan. 1)
- Medicare Advantage Open Enrollment: Jan. 1 – March 31 (for people already in an Advantage plan who want to switch or return to Original Medicare)
If you miss these windows, you may have to wait a year — unless you qualify for a Special Enrollment Period after a move, job change, or loss of coverage.
By the numbers
Medicare Part B premium, 2006–2026
The standard monthly Part B premium has climbed from $88.50 in 2006 to $202.90 in 2026. Hover any point for that year’s premium.
Source: CMS. Standard premium shown; in some hold-harmless years many existing enrollees paid less. Confirm at Medicare.gov.
By the numbers
How people get Medicare in Waukesha County
(MA penetration in Waukesha County)
MA penetration from CMS enrollment data; Medigap share is an estimate. U.S. average is about 54% Medicare Advantage. These are area-level figures, not plan-specific.
Explore
When can you enroll? An interactive year
Enrollment windows are federal and the same nationwide. Confirm your personal dates at Medicare.gov or 1-800-MEDICARE.
Explore
The parts of Medicare
Good to know
Frequently asked questions
Q: Does SHIP cost anything?
Q: Can SHIP or ADRC actually enroll me in a plan?
Q: What about Star Ratings — should I choose the highest-rated plan?
- CMS — MA/Part D Landscape & Plan Finder data
For personalized answers, contact Medicare.gov, 1-800-MEDICARE, or your local SHIP.