Medicare Advantage

Greenwich-Area Medicare Plan Choices for 2027

GREENWICH, Conn. — If you live in Greenwich or the surrounding towns, you have plenty of company when it comes to sorting through Medicare choices for 2027. The wider metro area — stretching from lower Fairfield County into nearby New York suburbs — is one of the more plan-rich corners of the Northeast, and this fall's Annual Enrollment Period is the moment to take a fresh look.

This snapshot focuses on how many plans are available in the area, not which ones to pick. Availability is set county by county by the Centers for Medicare & Medicaid Services (CMS), so where you live — even a few towns over — can change what's on your menu.

Greenwich sits in a plan-rich county

Greenwich is in Fairfield County, and that's the county CMS uses to determine which Medicare Advantage and Part D plans you can enroll in. For 2026, Fairfield County residents had 36 Medicare Advantage plans to consider, offered by 6 carriers providing Medicare Advantage with prescription drug coverage (MA-PD). The 2027 counts are reflected in each plan's ANOC and on Medicare.gov's Plan Finder.

That's a wide field. It's more than most Americans see nationally, and it reflects the density of the New York metro market that Greenwich sits inside.

What "area counts" actually mean

The counts above describe the shelf — how many products are on it — not the fit. Two Greenwich neighbors can look at the same 36-plan list and pick very different plans because their doctors, prescriptions, and travel habits differ.

A few things worth knowing about how availability works around here:

• Plans are county-based. If you drive over the border into Westchester County, N.Y., or up into New Haven County, the plan list changes. That matters for readers who split time between homes or are thinking about a move.
• Networks don't stop at the state line. Many Fairfield County plans include hospitals and specialists in New York City. Others are tighter. Always check the plan's provider directory before assuming.
• Stand-alone Part D looks different lately. Connecticut has 11 stand-alone Part D plans for 2026, sold statewide, and anyone in Fairfield County with Original Medicare can join one of them. Many residents instead get drug coverage bundled into Medicare Advantage (MA-PD). If you have Original Medicare and want drug coverage for 2027, use Medicare.gov's Plan Finder to see every Part D option available to your ZIP code — Connecticut has 10 stand-alone Part D plans for 2027, sold statewide.

Star Ratings in the local picture

CMS publishes Star Ratings each year to measure plan quality on things like customer service, member complaints, and preventive care. Ratings run from 1 to 5 stars.

Under CMS's 2026 Star Ratings, 3 of the 13 Medicare Advantage contracts offering plans in Fairfield County are rated 4 stars or higher, with 11 of the 13 contracts having a 2026 Star Rating at all. Ratings shift year to year — many contracts serve multiple states, and a lower star count in one cycle can rebound in the next. Use ratings as one input, not the whole decision.

The 2027 rules that apply everywhere — including Greenwich

No matter which plan you land on, some Medicare rules are set at the federal level. For 2027:

• Part D out-of-pocket cap: $2,400 in 2027 (it was $2,100 in 2026). Once your covered drug spending hits that ceiling, you pay nothing for covered drugs the rest of the year.
• Part D deductible: up to $700 in 2027 (up from $615 in 2026). Plans can charge less, but not more.
• The "donut hole" is gone. As of 2025, Part D has three phases, not four — deductible, initial coverage, and catastrophic.
• Medicare Prescription Payment Plan. You can ask your Part D plan to spread your drug costs across the calendar year in monthly installments instead of paying big amounts at the pharmacy counter.
• IRMAA. Higher-income beneficiaries pay extra for Part B and Part D. In 2026, the surcharge starts above $109,000 in income for a single filer.

Key dates to circle

• Oct. 15 – Dec. 7: Annual Enrollment Period. Add, drop, or switch Medicare Advantage or Part D coverage. Changes take effect Jan. 1.
• Jan. 1 – Mar. 31: Medicare Advantage Open Enrollment. If you're already in an MA plan, you get one chance to switch to a different MA plan or return to Original Medicare (and add a Part D plan).