Independent Medicare Broker Serving St. Augustine, FL
St. Augustine is an incorporated city in St. Johns County and one of the fastest-growing Medicare markets in northeast Florida. If you are turning 65 or reviewing your current Medigap coverage, William Gray is an independent Medicare insurance broker licensed in Florida since 1998. Call (386) 871-3858 to speak directly with William — not a call center — about Medicare Supplement options available in St. Augustine.
Your Independent Medicare Broker
William Gray
Founder of The Medicare Dude · Licensed Since 1998 · Independent Medicare Broker
Independent Medicare Broker serving St. Augustine, Florida
"Very Knowledgable and personable! William made a seemingly difficult transition easy and seamless. I appreciated his unbiased opinion and personalized what was best for me. He took great care in listening to my concerns. I never felt rushed and felt he took a personal interest in assisting me to make the best choice. Not one of those "Big box" sales as seen on TV. Highly recommend William."
Sharon H
Medicare client
5 ★ · 90 reviews
Medicare in St. Augustine
St. Augustine is located in St. Johns County, between Jacksonville to the north and Palm Coast to the south. Medicare Advantage and Part D plan availability is determined by county and by the residential ZIP code used for enrollment, so the plans available to a St. Augustine resident may differ from those available in other parts of Florida.
HCA Florida Flagler Hospital is the primary acute care hospital serving St. Augustine and St. Johns County. If you are comparing Medicare Advantage plans, confirming that your preferred hospital and specialists participate in a plan's network is an important step before enrolling.
St. Johns County is one of the fastest-growing counties in Florida. If you are comparing Medicare Supplement coverage, the plan letter and standardized benefits are the same regardless of which carrier you choose — but premiums can vary meaningfully from one company to another for the same plan.
St. Augustine and St. Johns County
St. Augustine is located in St. Johns County (FIPS 12109). The county relationship gives context for Medicare Advantage and Part D service areas, while a residential address is used to confirm an individual’s available options.
Residents comparing Medicare can benefit from first deciding whether Original Medicare or Medicare Advantage better fits their preferred way to receive care.
Turning 65 in St. Augustine — What to Expect
If you are approaching Medicare eligibility, your Initial Enrollment Period begins three months before the month you turn 65 and extends three months after. This is generally the most favorable time to enroll in a Medicare Supplement plan because federal guaranteed-issue rights apply — insurers cannot use medical underwriting to deny coverage or charge higher premiums based on your health history.
St. Augustine residents turning 65 have two main paths: Original Medicare (Parts A and B) with a Medicare Supplement plan and a standalone Part D drug plan, or Medicare Advantage (Part C) through a private insurer. The right path depends on your doctors, prescriptions, expected use of care, and how you want to manage out-of-pocket costs.
Medicare Supplement (Medigap) Plans in St. Augustine
Medicare Supplement insurance — also called Medigap — works alongside Original Medicare to help cover certain out-of-pocket costs such as deductibles, coinsurance, and copayments. Medigap plans are standardized by the federal government: a Plan G from one company covers the same core benefits as a Plan G from any other company. What differs between carriers is the premium, the company's financial strength, and its history of rate increases.
Plan G is one of the most comprehensive Medigap options available to people newly eligible for Medicare on or after January 1, 2020. Plan N offers a lower premium in exchange for copays on some office and emergency room visits. Because Medigap benefits are standardized, comparing premiums across carriers is one of the most practical steps a St. Augustine resident can take. An independent broker can pull real-time rates from multiple carriers — at no cost to you.
Medicare Enrollment Timing
The Initial Enrollment Period is an important time for people becoming eligible for Medicare. Medicare Advantage and Part D plans can also be reviewed during the Annual Enrollment Period, October 15 through December 7.
Florida does not currently provide a general annual Medigap Birthday Rule. Outside a Medigap Open Enrollment Period or another applicable guaranteed-issue right, changing Medicare Supplement coverage may require medical underwriting. An independent broker can explain the comparison process for a St. Augustine resident and help identify questions to ask.
Medicare Supplement guidance
Explore Medigap options for St. Augustine
Medicare Supplement policies work with Original Medicare. Compare plan basics, review Plan G and Plan N considerations, or request a no-cost conversation about your situation.
Medigap Resources
Nearby Communities
Want to understand how independent Medicare help works? Learn what a Medicare broker does before choosing help with your coverage.
Direct Personal Service
Work Directly With William in St. Augustine
Nearly 30 years of Medicare experience. One independent broker. Direct access — before, during, and after enrollment.
William answers his own phone.
When you call, you reach William directly — not a call center, not a rotating representative, not a voicemail queue.
Help before you enroll.
William explains your options, compares the plans available through the carriers he represents, and helps you choose coverage that fits your doctors, prescriptions, and budget.
Help during enrollment.
William walks you through the application process and makes sure your coverage is confirmed before your effective date.
Support after enrollment.
Questions don't end when the policy starts. William remains available when your coverage circumstances change, when you have billing questions, or when you want to review your options.
No carrier bias.
As an independent broker, William represents multiple insurance companies — not just one. His goal is to find the right fit for you, not to hit a quota for a single carrier.
No cost. No obligation. No pressure.
William's assistance — before, during, and after enrollment — is provided at no direct cost to you. Carriers compensate independent brokers; you do not pay a separate fee for William's guidance. There is no obligation to enroll, and no pressure to choose any particular plan.
No call centers · No carrier bias · Licensed in 15 states
What Clients Say
"I contacted William to assist my wife and I after moving to Florida from another state. He contacted us immediately and scheduled a phone appointment for the following week. We spent about an hour getting to know each other and our needs. He recommended several companies to match our needs and our location here in FL that we would NEVER had figured out on our own. Praise the Lord for Bill and for his help!! I would recommend him to anyone and everyone!!"
Jim M.
Medicare client · Verified Google Review
"Working with William Gray on my Medicare selections was an outstanding experience. Navigating Medicare can feel overwhelming, but William made the entire process simple, clear, and stress-free. He took the time to understand my specific needs, explained every option in a way that was easy to grasp, and offered thoughtful guidance without ever making me feel rushed or pressured."
Julie K.
Medicare client · Verified Google Review
"ABSOLUTELY GOD SENT! I knew nothing about Medicare and close to panicking before speaking with William. Super professional, well informed and kind! Anyone out there approaching 65 years old needs someone like William in their corner; he walked me through each step and all the options best suited my needs!!! All at NO COST because he is paid through the insurance companies."
JKC
Medicare client · Verified Google Review
"Navigating the healthcare system is complex to say the least. This is where The Medicare Dude, William Gray, shined for us on the road to consummating an ideal configuration for our unique and collective situations. William is not just a registered healthcare broker professional, but he is also a wealth of knowledge and sage consult in our best interests. He's always available when questions arise."
TinaKelvin B.
Medicare client · Verified Google Review
"I required an insurance broker with comprehensive knowledge in the field, and William Gray exceeded my expectations. He visited my home and provided a thorough explanation of various Medicare products. As a result, he helped me select the best supplement and achieve a significant reduction of over $150 per month in premiums."
Debra A.
Medicare client · Verified Google Review
"Very Knowledgable and personable! William made a seemingly difficult transition easy and seamless. I appreciated his unbiased opinion and personalized what was best for me. He took great care in listening to my concerns. I never felt rushed and felt he took a personal interest in assisting me to make the best choice. Not one of those "Big box" sales as seen on TV. Highly recommend William."
Sharon H.
Medicare client · Verified Google Review
Showing 6 of 90 verified Google reviews
Ready to Compare Medicare Options in St. Augustine?
No pressure. No cost. Just honest guidance from an independent agent who works for you — not an insurance company.
Prefer to talk? Call William — 1-800-DUDE-309 (800-383-3309)
Licensed in multiple states · Independent · No cost to you