Call Us: 207-987-5982


ABOUT US
Who We Are
The Orlando Insurance Agency is dedicated to helping our clients navigate the complex world of insurance. With a focus on Medicare, Individual/ACA, small group health, dental/hearing/vision, and retirement solutions, we strive to provide tailored options that meet each individual's needs. Our team is committed to offering personalized service and expert guidance to ensure our clients make well-informed decisions for their future and well-being.
At The Orlando Insurance Agency, our experienced professionals are passionate about delivering top-notch insurance solutions. We take pride in finding the best solution for you. Whether it's your small business, an individual Medicare solution, or your entire family looking for ACA coverage we'll guide you every step of the way!

Matt Orlando
Matt has extensive health insurance experience, with nearly 20 years of that experience in Medicare, and a deep understanding of plan design, sales and service, Matt is an excellent resource to guide you on your health insurance Journey.
Serving: Maine and New Hampshire (based out of Southern Maine)

Tom Rogers
Tom is a former teacher, history buff, and extremely knowledgeable benefit consultant. Tom is thorough, articulate, and takes great pride in guiding people through the complexity of Medicare. If you want someone in your corner... it's Tom!
Serving: Maine and New Hampshire (based out of Central Maine)

Cindy Cogswell
Cindy lives in Gray, Maine and has 35 years of experience in the insurance industry, with 25 years specializing in Medicare specifically. Cindy is extremely involved in the community and loves to help people with their Medicare decisions. Cindy has built her reputation around putting the needs of her clients above all else.
Serving: Maine and New Hampshire
(based out of Southern Maine)