Independent, 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.
If you're approaching Medicare eligibility or helping a loved one navigate enrollment, you need an advisor who understands the complex timing and coverage options that can affect your healthcare costs. A common mistake is missing enrollment windows or choosing plans that don't align with your health needs, leading to unexpected expenses.
- Surtax awareness. Confirm how they factor in Massachusetts' "Millionaire's tax" surtax on high incomes when planning your Medicare costs.
- Plan coordination. Ask how they integrate Medicare with your other insurance and retirement income to avoid coverage gaps.
- Independent advice. These advisors operate without firm constraints, so check how they present unbiased options across Medicare plans.
- Enrollment timing. Verify their approach to managing enrollment periods to prevent costly penalties or coverage lapses.
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 independent advice with a flat-fee structure that suits clients seeking clear cost expectations. With 39 years of experience and a ChFC® designation, she provides personalized financial planning from her Waltham, MA office, differentiating herself through a discovery-driven process and flexible fee options including hourly and retainer agreements.
Experience: 40 years
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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 assist with Medicare enrollment and coverage coordination in the Boston area. As an independent CFP®-certified advisor offering flat-fee comprehensive financial planning, she manages $30.1 million across 65 clients, providing personalized, unbiased advice without broker-dealer ties, which may appeal to those seeking transparent, integrated retirement and healthcare planning.
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, offering independent advice from Cambridge, MA, near Boston. With 20 years of experience and flat-fee options ranging from $1,000 to $5,000, he serves both individual and high-net-worth clients, providing asset management and financial planning with a focus on Social Security optimization and plan coordination.
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, offering independent advice with a flat-fee structure ranging from $4,000 to $9,000, suitable for high-net-worth clients in the Boston area. His firm emphasizes comprehensive financial planning with a globally diversified, tax-efficient investment approach, differentiating him through a blend of retirement, Social Security, and tax-loss harvesting expertise despite his relatively recent entry into the industry.
Experience: 1 year
Avg account: $4,112,722
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Renato M
Danvers, MA
Healthview Asset Management, Inc.
Renato Mastrogiovanni specializes in Medicare planning and long-term care insurance, offering independent advice from Danvers, MA, near Boston. His firm uses actuarial algorithms to project healthcare costs and provides flat-fee, discretionary portfolio management, distinguishing him with a healthcare-focused investment approach and leadership roles in retirement income organizations.
Experience: 11 years
Avg account: $580,006
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