Top medicare planning financial advisors working with high-net-worth individuals in Florida
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 timing and coverage choices that fit your unique financial picture. The biggest mistake is missing enrollment windows or selecting plans that don't align with your health needs and retirement goals.
- Coverage coordination. Confirm how they integrate Medicare with your existing health insurance and retirement income to avoid costly gaps.
- Cost management. Ask how they help balance premiums, deductibles, and out-of-pocket expenses to keep your healthcare affordable.
- Plan options insight. Look for advisors who explain differences between Medicare parts and supplemental plans in clear, simple terms.
- High-net-worth focus. These advisors understand how Medicare interacts with complex assets and can tailor strategies accordingly.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Barry S
Series 65
Alpharetta, GA
Wealth With No Regrets®
Barry Spencer's expertise in Medicare planning and retirement income strategy equips him to assist high-net-worth clients with navigating Medicare coverage and enrollment complexities. Operating from Alpharetta, GA, he offers flat-fee financial planning with fees negotiated per engagement, serving individuals, small businesses, and charitable organizations, and employs a blend of fundamental and technical analysis focused on long-term risk management and strategic judgment.
Experience: 14 years
Avg account: $842,438
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Christopher R
Series 65
Bonita Springs, FL
Sentinel Wealth Inc
Christopher Ragain specializes in Medicare planning for high-net-worth clients in Florida, leveraging 22 years of experience and a Series 65 designation to navigate complex retirement income and cash flow strategies. Unlike many advisors, he integrates tax and accounting services through his ownership of related businesses, offering flat-fee retirement plan advisory and a monthly Legacy BluePrint service that combines discretionary portfolio management with comprehensive financial oversight.
Experience: 22 years
Avg account: $1,700,652
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Daniel G
Series 65
Sarasota, FL
J. L. Bainbridge & Co., Inc.
Daniel Greenwald specializes in Medicare planning for high-net-worth clients in Florida, offering tailored strategies that consider complex assets and healthcare coverage coordination. Based in Sarasota, FL, he works with J. L. Bainbridge & Co., Inc., which emphasizes conservative growth and fixed-income portfolios, charging a 1.00% AUM fee. His background includes roles at Goldman Sachs and Deloitte, providing a blend of financial and industry experience despite his relatively recent entry into advisory services.
Experience: 1 year
Avg account: $1,620,861
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Benjamin D
CFP®, Series 65
Prospect, KY
The Gleason Group, Inc.
Benjamin Doninger specializes in Medicare planning and retirement income strategy, making him well-equipped to assist high-net-worth clients navigating Medicare in Florida. With 10 years of experience and CFP® certification, he works at The Gleason Group, Inc., a firm managing nearly $1 billion with a focus on goal-based planning and long-term, diversified investment strategies, charging a 1.50% AUM fee.
Experience: 10 years
Avg account: $6,006,358
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Arthur G
CFA®
Virginia Beach, VA
Martello Retirement and Wealth, LLC
Arthur Grizzle specializes in Medicare planning and retirement income strategy, making him well-equipped to assist high-net-worth clients in Florida approaching or in retirement. His firm, Martello Retirement and Wealth, LLC, offers a flat annual fee of $3,600 for comprehensive financial planning and employs a planning-first approach using passive ETFs and proprietary strategies, distinguishing him from advisors who may rely solely on active management or different fee structures.
Experience: 9 years
Avg account: $5,736,519
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