Don Lilly III — Medicare Supplement Agent
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Don Lilly III
Futurity First: Don Lilly Agency
(540) 380-8340
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Don Lilly III, MBA, LUTCF, LACP is the General Manager of the Don Lilly Agency of Futurity First Insurance Group, a retirement-focused insurance and financial services firm based in the Roanoke Valley of Virginia serving clients nationwide.
For more than 20 years, Don and his team have helped individuals and families navigate Medicare decisions, retirement income planning, life insurance, annuities, Social Security strategies, and long-term financial planning. His agency specializes in helping clients turning 65 understand their Medicare options while building retirement strategies designed to help protect income, reduce financial risk, and create long-term confidence in retirement.
Unlike captive insurance agencies that represent only one company, the Don Lilly Agency works with multiple nationally recognized insurance carriers and financial providers. This allows clients to compare Medicare Advantage plans, Medicare Supplement plans, Medicare Part D prescription drug coverage, life insurance options, annuities, and retirement solutions based on their individual healthcare needs and financial goals.
The agency is known for taking an educational approach to Medicare and retirement planning through one-on-one consultations, retirement reviews, educational workshops, and ongoing client support throughout the year — not just during Annual Enrollment Period.
In addition to Medicare planning, Don and his team assist clients with:
Medicare Advantage Plans
Medicare Supplement Insurance
Medicare Part D Prescription Drug Plans
Turning 65 Planning
Retirement Income Strategies
Social Security Coordination
Fixed Indexed Annuities
Wealth Management
ACA Health Insurance
Long-Term Care Planning
Life Insurance
Final Expense Insurance
Based in Roanoke, Don Lilly Agency serves clients locally and nationwide with licensed agents in all 50 states through in-person, phone, and virtual appointments.
Whether someone is preparing to retire, already enrolled in Medicare, or simply looking for a second opinion on their current coverage, Don and his team focus on helping clients make informed decisions with clarity, education, and personalized support.
Investment advisory services offered through Futurity First Wealth Management. Securities offered through registered representatives of a broker-dealer, member FINRA/SIPC.
For more than 20 years, Don and his team have helped individuals and families navigate Medicare decisions, retirement income planning, life insurance, annuities, Social Security strategies, and long-term financial planning. His agency specializes in helping clients turning 65 understand their Medicare options while building retirement strategies designed to help protect income, reduce financial risk, and create long-term confidence in retirement.
Unlike captive insurance agencies that represent only one company, the Don Lilly Agency works with multiple nationally recognized insurance carriers and financial providers. This allows clients to compare Medicare Advantage plans, Medicare Supplement plans, Medicare Part D prescription drug coverage, life insurance options, annuities, and retirement solutions based on their individual healthcare needs and financial goals.
The agency is known for taking an educational approach to Medicare and retirement planning through one-on-one consultations, retirement reviews, educational workshops, and ongoing client support throughout the year — not just during Annual Enrollment Period.
In addition to Medicare planning, Don and his team assist clients with:
Medicare Advantage Plans
Medicare Supplement Insurance
Medicare Part D Prescription Drug Plans
Turning 65 Planning
Retirement Income Strategies
Social Security Coordination
Fixed Indexed Annuities
Wealth Management
ACA Health Insurance
Long-Term Care Planning
Life Insurance
Final Expense Insurance
Based in Roanoke, Don Lilly Agency serves clients locally and nationwide with licensed agents in all 50 states through in-person, phone, and virtual appointments.
Whether someone is preparing to retire, already enrolled in Medicare, or simply looking for a second opinion on their current coverage, Don and his team focus on helping clients make informed decisions with clarity, education, and personalized support.
Investment advisory services offered through Futurity First Wealth Management. Securities offered through registered representatives of a broker-dealer, member FINRA/SIPC.
Products Offered:
Medicare Supplement, Medicare Advantage, Life Insurance, Health Insurance, Final Expense, Dental Plans, Annuities, Long Term Care, Disability Insurance, Retirement Planning, Mortgage Protection, Prescription Drug Plans, Short Term Medical, Home Health Care, Cancer/Heart/Stroke, Accident Insurance, Financial Advisors, Investment Services
States Serviced
VA, WV, NC, SC, KY, MD, DC, OH, NY, FL, TX, NJ, CT, IL, IN
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Articles & Insights from Don Lilly III
Jul 20, 2026
Mastering Medicare: Your AEP Survival Guide
The Medicare Annual Enrollment Period (AEP) comes around every fall, but for many beneficiaries, it still brings confusion, stress, and missed opportunities. If you’re enrolled in Medicare or about to become eligible, understanding how to make the most of this window can mean better coverage, lower costs, and greater peace of mind. Here’s how to take control of your Medicare decisions this AEP.
Jul 20, 2026
Does Medicare Cover All Healthcare Services?
Medicare provides broad coverage for many essential healthcare needs, but it does not cover everything. It is important to understand what is and is not included, so you can plan ahead, avoid unexpected expenses, and decide whether a Medicare Advantage plan or a Medicare Supplement (Medigap) plan is right for you. In this post, we outline what Original Medicare covers, where the gaps are, and what options you have for protection from unexpected out-of-pocket costs.
Jul 20, 2026
What to Know About the Medicare Initial Enrollment Period
Enrolling in Medicare to secure affordable healthcare coverage is a milestone for many individuals approaching retirement. The Initial Enrollment Period (IEP) is a crucial time in this process. It is a limited window of time during which you can sign up for Medicare without facing penalties or gaps in coverage. To make informed choices and avoid costly mistakes, it is important to understand how the IEP works.
Jul 20, 2026
Special Enrollment Periods: Taking Advantage of Flexible Medicare Options
Enrolling in Medicare can seem overwhelming, particularly when life changes occur outside the standard enrollment windows. Special Enrollment Periods (SEPs) offer flexibility for individuals who experience certain qualifying events. They allow these individuals to enroll in, drop, or change Medicare coverage without waiting for the next Open Enrollment Period. Knowing how SEPs work can help you make timely decisions and avoid gaps in your healthcare coverage.
Jul 20, 2026
Managing Chronic Conditions with Medicare Special Needs Plans (SNPs)
Living with a chronic health condition often involves juggling medications, frequent doctor visits, and ongoing care. Medicare Special Needs Plans (SNPs) are designed to make these challenges easier by offering coordinated healthcare and personalized coverage for individuals with specific medical needs.
Jul 20, 2026
Is Home Care or Hospice a Better Option When it Comes to Medicare?
Home health is designed for short-term, medically necessary recovery at home. It supports a recent illness, injury, or surgery when you need skilled nursing or therapy to regain function. Hospice is for a life-limiting illness when the focus shifts from cure to comfort and quality of life. You can receive many of the same disciplines (nurse, aide, social work), but the goal is symptom control, not rehabilitation or curative treatment for the terminal diagnosis.
Jul 20, 2026
A Closer Look at Medicare Coverage of Cataract Surgery in 2026
Facing cataract surgery? Discover how Medicare covers this common procedure, including benefits and what to expect regarding your out-of-pocket costs. Get informed before your appointment!
Jul 20, 2026
Does Medicare Cover Ambulance and Air Ambulance Services?
Emergencies happen suddenly and move fast. Families naturally focus on getting a loved one to the hospital and worry later about the costs. Medicare does cover many ambulance trips, but the rules are specific, and misunderstandings can lead to surprise bills.
Medicare Advantage
Jul 20, 2026
What You Should Know About Medicare Advantage Networks
Imagine scheduling a routine follow-up with your favorite doctor, only to learn later that the visit was out-of-network for your new Medicare Advantage plan. The bill could be higher than expected even though the medical care itself went smoothly. Understanding how networks work helps you avoid that kind of surprise.
Medicare Advantage
Jul 20, 2026
Original Medicare vs Medicare Advantage
Medicare choices can feel like picking a lane on a freeway with ten exits in the next mile. The core decision for many beneficiaries is whether to stay with Original Medicare, Part A plus Part B, or enroll in a Medicare Advantage plan, also called Part C. Both paths can work well, but they manage costs, networks, and add-on coverage in different ways, so the best fit depends on how you use care and who you want access to.
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