Helping You Understand The A, B, C’s and D’s of Medicare.

In-Person Meetings Available In Orlando And Surrounding Areas.

CALL: 1.800.936.5165

About Dale Wondisford

Learn more about Dale Wondisford of the Medigap Supplement Headquarters, where we help you understand the A’s, B’s, C’s, and D’s of Medicare.

Empowering Your Retirement Journey: Seamlessly Navigate Financial Planning and Medicare Health Options

As a seasoned advisor specializing in retirement guidance, I offer a comprehensive solution to address your evolving needs. With a deep understanding of financial intricacies and Medicare complexities, I am committed to crafting a personalized roadmap that ensures your golden years are not just secure but truly fulfilling.

My approach goes beyond mere numbers; it’s about understanding your unique aspirations, concerns, and lifestyle preferences. Through meticulous financial planning, I optimize your resources, maximizing returns while mitigating risks. Whether it’s retirement savings, investments, or estate planning, I provide tailored strategies to safeguard your financial well-being and legacy.

Navigating the labyrinth of Medicare can be daunting, but with my expertise, it becomes a streamlined process. From deciphering coverage options to optimizing benefits, I simplify the choices, ensuring you have access to the healthcare solutions that best suit your needs and budget.

With a focus on transparency, integrity, and unwavering commitment to your success, I am your trusted partner in realizing the retirement you’ve always envisioned. Let’s embark on this journey together, with confidence and clarity every step of the way.


Fill out the form to get your questions answered by Dale Wondisford wih a FREE no-obligation consulation.


Dale Wondisford has 15 years of experience helping people save hundreds and even thousands of dollars by showing his clients all of their Medicare options.

 His mission is to help people get the best coverage for their unique needs to enjoy their senior years with quality healthcare coverage.

That’s why Dale created Medigap Supplement Headquarters! Dale, “The Medicare Specialist,” is an experienced independent agent dedicated to helping you get the best coverage by providing free consultations and high-quality, top-notch service.

Don’t miss out on your chance to get the coverage you deserve with the help of someone who cares. Contact Dale today.

Laina Roy
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I have had the opportunity to have meet Dale approximately 7 years now. I have never had someone take the time to check what’s the best way to insure myself. He does a very in depth review of what was going on with health issues and the medications, in order to place me with an insurance that’s going to save on my costs
Mark Poff
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Dale is very knowledgeable and experienced working with the many offered medicare plans finding the best plan that benefits his clients which he did for my wife and I. I highly recommend Dale as I totally respect his judgement of which plan is best for the client.
Richard Hibbard
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Dale is really helpful he will get you a answer to any questions you may have. He even got on a three way call so we could hear what was going on. He always returns your call promptly. Dale is very knowledgeable about all types of insurance. Very friendly and no pressure tactics to buy. Would highly recommend Dale.