Independent Medicare Broker — Midtown Manhattan
Medicare Agent in Midtown Manhattan, NY
Our office is at 260 Madison Avenue, right in the heart of Midtown. Whether you’re turning 65 while still working, retiring from a Midtown firm, or reviewing your existing coverage — Craig Smith is here to help, always free.
📅 Schedule a Free Consultation
Or call Craig directly: 917-740-1895
Midtown Manhattan is home to one of the highest concentrations of professionals turning 65 while still actively employed anywhere in the country. For many Midtown residents — attorneys, executives, consultants, financial professionals, and business owners the Medicare decision is more complicated than it is for retirees. You may be covered under an employer group health plan, a spouse’s plan, or a business-funded policy, and understanding how Medicare interacts with those plans is critical to avoiding costly mistakes.
Craig Smith Insurance Group’s office is located at 260 Madison Avenue, 8th Floor, within walking distance from most Midtown offices. We specialize in helping working professionals navigate the Medicare enrollment decision, coordinate coverage correctly, and choose the right supplemental plan when the time comes. Every consultation is free.
Turning 65 While Still Working in Midtown — What You Need to Know
For Midtown professionals, the Medicare enrollment decision typically centers on one question: should you enroll in Medicare now, or delay? The answer depends on your specific employment situation, and getting it wrong can be costly.
| Your Situation | Medicare Enrollment Guidance |
|---|---|
| The employer has 20+ employees | Your employer group plan is primary. You can delay Medicare Part B without penalty and enroll during a Special Enrollment Period when your employment or coverage ends. However, enrolling in Part A now is usually recommended since it’s typically free and provides a secondary coverage layer. |
| The employer has fewer than 20 employees | Medicare becomes primary at 65 regardless of whether you’re still working. If you don’t enroll in Part B on time, your employer plan may not pay claims correctly — and you could face a permanent Part B late enrollment penalty. |
| Self-employed or business owner | This depends on how your coverage is structured. If you’re covered under an individual policy rather than a true group employer plan, Medicare may still be required at 65. This is a common source of confusion for Midtown entrepreneurs and consultants — Craig can walk through your specific situation. |
| Covered under a spouse’s employer plan | If your spouse is actively employed and you’re covered under their group plan, you may be able to delay Medicare Part B without penalty — as long as the employer has 20 or more employees. When that coverage ends, you have 8 months to enroll in Part B through a Special Enrollment Period. |
| High income — IRMAA may apply | Midtown professionals frequently have incomes that trigger IRMAA surcharges on Medicare Part B and Part D premiums. These surcharges are based on income from two years prior. Use our IRMAA Calculator to see whether this applies to you, and our IRMAA Brackets 2027 guide for upcoming year planning. |
⚠️ 2026 Network Alert — Midtown Manhattan Residents
Several major Medicare Advantage carriers have experienced significant network disruptions with Manhattan hospital systems in 2026. If you are currently enrolled in a Medicare Advantage plan, it’s worth verifying that your Midtown-area doctors and hospitals remain in-network. Craig Smith Insurance Group can review your current coverage and compare alternatives at no cost. Call 917-740-1895 or schedule a free review.
Medicare Services for Midtown Manhattan Professionals
🏢 Employer Coverage Coordination
We help working professionals understand exactly how Medicare interacts with their employer plan — and when and how to transition to Medicare without gaps or penalties.
💰 IRMAA Planning
For higher-income Midtown professionals, IRMAA surcharges can add hundreds per month to Medicare costs. We help you understand your surcharge level and plan accordingly.
🔍 Plan Comparison
We compare every Medicare Advantage, Medigap, and Part D plan available in your Midtown ZIP code and recommend based on your specific situation — not what pays us the most.
👨⚕️ Doctor Verification
We verify that your current Midtown-area and Manhattan doctors are in-network before recommending any Medicare Advantage plan.
📋 Enrollment Timing Guidance
We help you identify the correct enrollment window based on your employment situation, avoiding the permanent late enrollment penalties that catch many Midtown professionals off guard.
📞 In-Person Midtown Meetings
Our office at 260 Madison Avenue, 8th Floor is convenient to most Midtown offices. In-person consultations are available by appointment, always free.
Choosing Between Medicare Advantage and Medigap in Midtown
Medicare Advantage
Often $0 premium with drug and extra benefits included. However, Midtown Manhattan has complex hospital network relationships — especially with top medical centers. Craig verifies your specific providers before recommending any Advantage plan.
Medicare Supplement (Medigap)
Higher monthly premium, but you can see any Medicare-accepting doctor nationwide — no networks, no referrals, no prior authorizations. For busy Midtown professionals who value simplicity and access, Medigap often provides the best long-term fit. New York’s guaranteed issue rights mean you can enroll year-round.
For a detailed comparison, see our Medicare Advantage vs. Medicare Supplement guide.
⭐⭐⭐⭐⭐ 317+ Five-Star Google Reviews
Craig Smith Insurance Group has earned over 317 combined five-star reviews. Midtown clients frequently highlight Craig’s understanding of working-professional Medicare situations — including employer plan coordination and IRMAA planning. Read our client reviews →
Frequently Asked Questions — Medicare in Midtown Manhattan
I’m still working at 65 and have employer coverage. Do I need to enroll in Medicare?
It depends on your employer’s size. If your employer has 20 or more employees, you can generally delay Part B without penalty while covered by an active employer plan. If your employer has fewer than 20 employees, Medicare becomes primary at 65 even if you’re still working. Getting this wrong can result in permanent late enrollment penalties and coverage gaps. Craig walks through your specific situation to make sure you get it right.
What is the IRMAA surcharge, and does it affect me?
IRMAA is an additional surcharge added to your Part B and Part D premiums if your income exceeds certain thresholds. It’s based on your tax return from two years prior. Given Midtown Manhattan’s high concentration of professional incomes, IRMAA affects many of our clients. Use our IRMAA Calculator to check whether it applies to you and how much it may add to your monthly premium.
Where is Craig Smith’s Midtown office?
Craig Smith Insurance Group is located at 260 Madison Avenue, 8th Floor, New York, NY 10016, in the heart of Midtown Manhattan. In-person appointments are available at a time convenient to your schedule, completely free of charge.
Also serving nearby Manhattan neighborhoods and Nassau County
Craig Smith Insurance Group serves clients throughout Manhattan, including the Upper West Side and all of New York City. We also serve Nassau County communities including Lake Success, Roslyn, and New Hyde Park.
Visit Our Midtown Office — 260 Madison Avenue
Craig Smith Insurance Group is located at 260 Madison Avenue, 8th Floor, Midtown Manhattan. In-person, phone, and virtual consultations are all available — and always free.
📅 Schedule Your Free Consultation
Or call: 917-740-1895 | craigsmith@csmedicare.net
Craig Smith Insurance Group | 260 Madison Avenue, 8th Floor, New York, NY 10016 | Independent Medicare Broker | Licensed in New York, New Jersey, and 14 additional states
We are not connected with or endorsed by the United States Government or the federal Medicare program. We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
