Top medicare planning financial advisors in Bridgeport, CT
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.
Medicare planning becomes crucial when you’re approaching age 65 or already enrolled and need to navigate coverage options and costs. Without expert guidance, it’s easy to miss enrollment deadlines or choose plans that don’t fit your health needs and budget.
- Enrollment timing. Confirm how the advisor helps you avoid penalties by managing your initial and special enrollment periods.
- Plan comparison. Look for advisors who explain differences between Medicare Parts A, B, C, and D clearly, helping you pick the right combination.
- Cost management. Ask how they evaluate premiums, deductibles, and out-of-pocket limits to balance coverage and expenses.
- Supplemental coverage insight. Ensure they discuss Medigap policies or Medicare Advantage plans tailored to your health profile and financial goals.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Kyle M
CFP®
Danbury, CT
Matson Financial Advisors, Inc.
Kyle Matson specializes in Medicare planning and retirement income strategy, offering clear guidance on enrollment timing and plan comparisons to help manage costs effectively. Based in Danbury, CT, his firm provides flat-fee financial consultations and serves high-net-worth clients with a comprehensive planning approach that includes estate and charitable giving strategies, distinguishing him from other advisors in the Bridgeport area.
Experience: 1 year
Avg account: $2,244,473
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Legrand R
CFP®, Series 63, Series 65
Stamford, CT
Asset Management Group, Inc.
Legrand Redfield Jr. offers Medicare planning expertise combined with 47 years of industry experience, making him well-equipped to guide clients through enrollment timing and plan comparisons. His firm provides comprehensive financial planning with a flat fee structure ranging from $2,500 to $10,000, emphasizing asset allocation and manager selection, which distinguishes him from other advisors in the Bridgeport area.
Experience: 47 years
Avg account: $3,427,069
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Jeffrey R
CFP®, Series 63, Series 65, Series 66
Port Jefferson Station, NY
Aventine Financial Group
Jeffrey Roberto offers Medicare planning expertise with 23 years of experience and CFP® certification, helping clients navigate enrollment timing and plan comparisons effectively. Based in Port Jefferson Station, NY, he serves high-net-worth clients with a flat-fee structure and employs both fundamental and technical analysis for long-term investment strategies, distinguishing him from other advisors in the Bridgeport, CT area.
Experience: 23 years
Avg account: $1,125,540
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James B
Series 66
Fairfield, CT
Merrill
James Brown specializes in Medicare planning and elder care, making him well-suited to help Bridgeport residents navigate Medicare options and costs. Based in nearby Fairfield, CT, he works at Merrill, a large firm, and offers a managed strategy fee of 1.10% for accounts under $2 million, focusing on mid-career professionals and high earners with diverse financial priorities.
Experience: 2 years
Avg account: $860,085
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Gilbert D
Series 65
Fairfield, CT
GCD Financial Planning and Advisory Services
Gilbert Donovan III specializes in Medicare planning and Social Security optimization, offering tailored guidance on enrollment timing and plan comparisons to help manage costs effectively. Operating independently with a flat-fee structure, he brings four years of experience and a background at U.S. Bank, serving clients from Fairfield, CT, with a focus on comprehensive retirement and cash flow planning.
Experience: 4 years
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