Top medicare planning financial advisors in Boston, MA
The right financial advisor for you depends on how you weigh location, expertise, experience, the clients they typically serve, and how they work with you.
You need a Medicare planning advisor if you're approaching age 65 and want to navigate enrollment periods, coverage options, and costs without costly mistakes. A common pitfall is missing deadlines or choosing plans that don't fit your health needs or financial situation.
- Enrollment timing. Confirm how they help you avoid penalties by managing initial and special enrollment periods.
- Coverage coordination. Ask how they balance Medicare parts A, B, C, and D with supplemental plans to minimize out-of-pocket expenses.
- Tax impact awareness. In Massachusetts, high incomes may trigger extra surtaxes; check how they factor this into your plan choices.
- Cost forecasting. Ensure they model your expected medical needs and premiums over time, not just the current year.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Penelope T
ChFC®, Series 63
Waltham, MA
Wealthy Choices (R)
Penelope Tzougros specializes in Medicare planning and long-term care insurance, offering expertise crucial for navigating enrollment periods and coverage coordination near Boston. With 39 years of experience and a flat-fee structure starting at $1,000 annually, she provides independent, personalized financial planning that includes tax and estate considerations, distinguishing her from advisors with less comprehensive service models.
Experience: 40 years
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Mark T
Series 66
Boston, MA
Merrill
Mark Tsoir specializes in Medicare planning in Boston, leveraging Merrill's large-firm resources to help clients navigate enrollment periods and coverage coordination. With a focus on mid-career professionals and high earners, he offers a 1.10% AUM fee for managed strategies under $2 million, and provides multilingual support in Russian, Hebrew, and English, distinguishing him from other advisors in the area.
Experience: 2 years
Avg account: $860,085
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Kate C
CFP®
Salem, MA
Red Clover Wealth Management, LLC
Kathleen Cote specializes in Medicare planning and income planning, making her well-equipped to help clients in the Boston area navigate Medicare enrollment and coverage options. As a CFP®-certified independent advisor offering flat-fee comprehensive financial planning, she manages $30.1 million across 65 clients, providing personalized, discretionary portfolio management without broker-dealer conflicts.
Experience: 14 years
Avg account: $463,183
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Robert M
Series 63, Series 65
Cambridge, MA
Davinci Capital Management, Inc.
Robert Mcgowan specializes in Medicare planning and retirement income strategy, making him well-equipped to assist with Medicare enrollment and coverage coordination in the Boston area. His firm offers flat-fee financial planning ranging from $1,000 to $5,000, serving both individual and high-net-worth clients with a non-discretionary, analytical approach, distinguishing him from advisors with purely asset-based fees.
Experience: 21 years
Avg account: $591,127
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Samuel L
Series 65
Newtonville, MA
Levenson Wealth LLC
Samuel Levenson specializes in Medicare planning and tax strategies, helping clients navigate enrollment periods and coverage coordination in the Boston area. His firm offers flat-fee, project-based planning with a focus on tax efficiency and diversified investments, catering to high-net-worth individuals seeking comprehensive retirement and Social Security optimization alongside Medicare guidance.
Experience: 1 year
Avg account: $4,112,722
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