Seasoned, medicare planning financial advisors in Massachusetts
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.
When you or a loved one become eligible for Medicare, navigating enrollment periods and coverage options can feel overwhelming. A common mistake is missing deadlines or choosing plans that don't align with your health needs and budget.
- Enrollment timing. Confirm how they help you avoid penalties by enrolling during the right periods.
- Plan comparison. Ask how they evaluate Medicare Advantage, Part D, and supplemental plans to fit your specific medical and prescription needs.
- Cost management. Discuss how they balance premiums, deductibles, and out-of-pocket expenses to keep your healthcare affordable.
- Coordination with other benefits. Check if they consider how Medicare interacts with employer coverage or Medicaid to prevent coverage gaps.
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 offers extensive expertise in Medicare planning, supported by 39 years of industry experience and a ChFC® designation, making her well-equipped to guide Massachusetts clients through enrollment timing and plan comparisons. Her firm, Wealthy Choices, emphasizes a discovery-driven planning process with flexible flat-fee and hourly compensation, catering to individuals and families seeking personalized, independent advice beyond Medicare, including long-term care insurance and estate planning.
Experience: 40 years
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Kevin C
CFP®, Series 63
Wells, ME
Salem Advisory Group LLC
Kevin Colley brings 27 years of experience and CFP® certification to Medicare planning, offering expertise in balancing premiums, deductibles, and out-of-pocket costs to help manage healthcare affordability. Based in Wells, ME, he operates through Salem Advisory Group LLC, which serves individual investors and trusts with fee-based investment management and financial planning, using fundamental and technical analysis and negotiable fees ranging from 0.1% to 1.5% AUM.
Experience: 28 years
Avg account: $249,370
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Arthur R
Series 63, Series 65
Bluffton, SC
Strategic Investment Solutions, LLC
Arthur Randall brings 21 years of experience and specializes in Medicare planning alongside income and Social Security optimization, which is crucial for managing healthcare costs effectively. Operating from Bluffton, SC, he offers independent advice with a fee structure of 1.25% AUM or $150 hourly, and his firm emphasizes tax-managed portfolios and income-focused solutions, differentiating him from advisors who may not integrate investment strategies with Medicare planning.
Experience: 22 years
Avg account: $303,971
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Gregg S
ChFC®, Series 63
Cambridge, MA
Davinci Capital Management, Inc.
Gregg Semprucci brings 37 years of experience in Medicare planning and retirement income strategy, making him well-equipped to assist with Medicare enrollment timing and plan comparisons in Massachusetts. Operating from Cambridge, MA, he offers flat-fee financial planning ranging from $1,000 to $5,000 and serves both individual and high-net-worth clients, distinguishing himself with a broad insurance background and a non-discretionary investment approach through Davinci Capital Management.
Experience: 38 years
Avg account: $591,127
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Dennis M
CFP®, Series 63
Sturbridge, MA
McCurdy & Andrew Investments, LLC
Dennis McCurdy offers seasoned expertise in Medicare planning, backed by 37 years in the industry and CFP® certification, making him well-equipped to guide Massachusetts clients through enrollment timing and plan comparisons. His firm employs a fundamental, asset-allocation investment approach and provides flat-fee financial planning, which may appeal to those seeking transparent costs alongside comprehensive retirement and tax planning services.
Experience: 38 years
Avg account: $332,440
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