I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, and my office is in Fort Lauderdale, just up Andrews Avenue from Wilton Manors. Over 14 years I’ve helped more than 1,800 people sort through health and Medicare plans by looking at what matters to them: their doctors, their prescriptions and what they can comfortably spend each year. I’d be glad to do the same for you and your household in the Island City.
You’ll get plain answers, no pressure, and an agent who is still here after the paperwork is done. Book a free plan review and I’ll get back to you myself within 24 to 48 hours.
Years in Insurance
Clients Helped
Client Retention
HealthMarkets Agent, 2022–2026
As an independent agent with HealthMarkets, I’m not tied to one insurance company. I compare plans from multiple carriers so you see real options side by side, and I stay involved long after you enroll.
Hear how I help you choose a plan with confidence.
Maria F., (read review on Google Maps)
Roxroy is a miracle worker! He got my mother’s insurance company to expedite the review of a surgery she needed, which otherwise would have taken far too long to be approved. I truly cannot say enough good things about him.
His dedication, compassion, and willingness to go above and beyond made all the difference for our family. We are incredibly grateful for his help!
David F., (read review on Yelp)
Wilton Manors sits between several hospitals. Holy Cross Health is just east of the city on North Federal Highway, Broward Health Imperial Point is a short drive north on Federal Highway, and Broward Health Medical Center is south in downtown Fort Lauderdale (Holy Cross Health, Broward Health Imperial Point, Broward Health Medical Center).
Having a hospital nearby and having it covered by your plan are two different things, because every plan has its own network. Before I recommend anything, I check your doctors, hospitals, prescriptions and pharmacy against each plan we’re considering, and if the answer isn’t clear I pick up the phone and call your doctor’s office myself.
Because Wilton Manors is only a few miles from my office, it’s easy to meet face to face, to get help with a claim or a bill after you enroll, and to sit down together for your annual coverage review. I work with clients across the city, including Highland Estates, Jenada Isle, Coral Gardens, Middle River Estates, Wilton Station and the Westside area along Powerline Road. I also serve neighbors in Oakland Park, Lazy Lake, Fort Lauderdale and Lauderdale-by-the-Sea.
From Wilton Drive or NE 26th Street, head west to North Andrews Avenue and take Andrews north about three and a half miles to Cypress Creek Road. Turn left (west) onto Cypress Creek Road, go a few blocks, and turn right (north) onto NW 5th Way.
If you’d rather use the highway, take Oakland Park Boulevard west to I-95, go north one exit to Exit 33B (Cypress Creek Road West), then head west on Cypress Creek Road a few blocks and turn right onto NW 5th Way. Either way, you’ll find my office at 6360 NW 5th Way, Suite 101, Fort Lauderdale, FL 33309.
Park in the building’s lot and come to Suite 101 on the ground floor. If anything is hard to find, call me at 954-410-3710 and I’ll point you the right way.
Prefer to meet at home? I also make home visits throughout Wilton Manors and the rest of Broward County.
I’m available for in-person appointments, at my Fort Lauderdale office or at your home, all over Broward County, including every city listed below.
Fort Lauderdale, Pembroke Pines, Hollywood, Miramar, Coral Springs, Pompano Beach, Davie, Sunrise, Plantation, Deerfield Beach, Lauderhill, Tamarac, Weston, Margate, Coconut Creek, North Lauderdale, Oakland Park, Hallandale Beach, Lauderdale Lakes, Parkland, Cooper City, Dania Beach, West Park, Wilton Manors, Lighthouse Point.
Enrollment and Timing
Most households need more than one kind of coverage, and what you need changes as life does. See all the coverage I help with and my guides to each type of insurance:
Do You Serve Wilton Manors, and How Can We Meet?
Yes. Wilton Manors is one of the closest cities to my Fort Lauderdale office, and I have clients throughout it. We can meet at my office, at your home, over the phone or on Zoom, whichever suits you.
What Can You Help Me With in Wilton Manors?
A large share of my work is Medicare: Medicare Advantage, Medicare Supplement (Medigap) and Part D prescription drug plans, along with guidance for people turning 65 or retiring from employer coverage. I also help individuals and families with ACA Marketplace and off-Marketplace plans, small business owners with group plans for 50 or fewer employees, and self-employed people who need coverage of their own.
If you may qualify for Extra Help, Medicare and Medicaid dual eligibility, a Special Needs Plan or a Special Enrollment Period, I can walk you through it. I also offer dental, vision, life and supplemental insurance, so your whole household’s coverage can be handled by one person.
How Do You Compare to Other Health Insurance Agents in Wilton Manors?
If you call a call center, or an agency that hands clients from one person to the next, you may end up explaining your situation to someone new every time. With me, the person you talk to is always the same: me. You have my direct line, there’s no assistant or call center in between, and I reply within 24 to 48 hours.
People tell me about agents who were hard to reach, call-backs that never came, phones answered by an automated system, and nobody around once a problem came up after enrollment. My approach is different. I begin by asking about your health, your budget, your doctors and your prescriptions, then I show you a full-year cost estimate for each option and go through it at your pace. After you enroll, I help with claims and billing, and I review your coverage with you every year.
I bring 14 years in insurance, I’ve been named a Top 100 HealthMarkets agent every year from 2022 through 2026, and I’m licensed in 33 states. You can verify my license (Florida License #W323530, NPN #17946070) through the Florida Department of Financial Services. My help is free to you, since premiums are generally the same whether you enroll through me or directly with the insurance company.
Do You Offer Every Medicare Plan in Wilton Manors?
No. We do not offer every plan available in your area. Currently we represent 8 organizations which offer 65 products in your area. Please contact Medicare.gov or 1-800-MEDICARE (TTY users should call 1-877-486-2048), 24 hours a day, 7 days a week, to get information on all of your options. In Florida, you can also get free Medicare counseling through the state’s SHIP program, called SHINE.
Does It Cost Anything to Work With You?
No. Plan premiums are generally the same whether you enroll through me or directly with the insurance company, so my help and the support that follows come at no extra cost to you. Your quote and plan review are free, and you’re under no obligation to enroll.
Keep in mind that the premium is only one piece of what a plan costs over a year. I add up the deductible, copays, drug costs and out-of-pocket maximum to give you a realistic full-year estimate. You may qualify for financial help with a Marketplace plan or with Medicare prescription drug costs, and if so, I’ll explain how that works.
Will My Plan Cover the Hospitals and Doctors Near Wilton Manors?
That depends on the plan, since each one has its own network. Give me the names of your doctors, the hospitals you prefer and the pharmacy you use, and I’ll check them against every plan we compare. If anything is uncertain, I’ll call your doctor’s office to confirm.
When Should I Start Looking at Plans?
Medicare’s Annual Enrollment Period for 2027 plans runs from October 15 to December 7, 2026, and changes take effect January 1, 2027. For ACA Marketplace plans, Open Enrollment for 2027 coverage opens November 1, 2026, and you need to enroll by December 15, 2026 for coverage that starts January 1, 2027.
Turning 65 brings its own seven-month Initial Enrollment Period around your birthday, and losing job-based coverage or moving can open a Special Enrollment Period. Starting early gives us time to compare carefully. Get your free quote and I’ll help you pin down your dates.
I’ve spent 14 years in insurance and the last 8 focused on Medicare. Before that, I built a background in business and technology, with a Master’s in Business and a BA in Information Technology, which is a big part of why I like turning complicated plan details into something clear.
My approach is education first. I take the time to understand each client individually, explain your options step by step, and let you make the call. I’m proud that more than 8 out of 10 of my clients stay with me year after year, based on my own client records. To me, that’s the real measure of whether I did my job.
Want to learn at your own pace? Start with my Knowledge base, or check out my TikTok videos, where I break down Medicare in a minute or two.
Tell me where you are in South Florida and what you need help with, and I’ll pick a time that works, at my office, at your home, by phone or on Zoom. Bring your list of doctors, your medications and your current plan if you have one, and I’ll walk through your options. My help never costs you anything extra.
Call or text: (954) 410-3710
Email: contact@chaperonehealthinsuranceplus.com
Office: 6360 NW 5th Way Ste 101, Fort Lauderdale, FL 33309
Meet by: phone, video, at my office, or at home in Broward, Miami-Dade and Palm Beach.
Five steps, no pressure, and I stay with you after you enroll.
By phone, Zoom or face to face. Your health, your budget, your doctors.
Doctors, hospitals, prescriptions and pharmacy, checked against each plan.
A full-year estimate for each option, explained in plain language.
No pressure. If you choose a plan, I handle the application with you.
Plans and networks change. I check yours each year and help with claims in between.