I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, and my office is in Fort Lauderdale. Over the past 14 years I’ve sat down with families and retirees to compare health and Medicare plans one next to the other, starting with the doctors they see, the medications they take and what they can comfortably spend, and I’d like to do the same for you in Sunrise.
I explain everything in everyday language, I never rush a decision, and once you’re enrolled I remain your agent. Book a free plan review and you’ll hear back from me personally 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)
Sunrise sits within a short drive of several hospitals, among them HCA Florida Westside Hospital on West Broward Boulevard in Plantation, HCA Florida University Hospital in Davie, Cleveland Clinic Weston Hospital in Weston and HCA Florida Woodmont Hospital in Tamarac (HCA Florida Westside, HCA Florida University, Cleveland Clinic Weston, HCA Florida Woodmont).
Having a hospital nearby is one thing; having it in your plan’s network is another, and every plan draws its network differently. Before I recommend anything, I run your doctors, hospitals, prescriptions and pharmacy against each plan we’re considering, and if a detail isn’t clear I pick up the phone and call your doctor’s office myself.
Because my office is only a short drive east of Sunrise, it’s simple to meet face to face, to get help with a claim or a bill after you’ve enrolled, or to go over your coverage together each year. I work with clients across Sunrise, including Sunrise Lakes, Welleby, Springtree, Sawgrass, Sunrise Golf Village and New River Estates. I also serve the neighboring communities of Plantation, Tamarac, Lauderhill, Davie and Weston.
From most of Sunrise, take Oakland Park Boulevard east to I-95 and go north one exit to Exit 33B (Cypress Creek Road West). If you’re in the southeastern part of the city near Sunrise Boulevard, head east on Sunrise Boulevard to I-95 north and stay on it to Exit 33B.
Once you leave the interstate, continue west on Cypress Creek Road for a few blocks and turn right onto NW 5th Way. My office is 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 you have any trouble finding it, call me at 954-410-3710.
Prefer to meet at home? I also make home visits throughout Sunrise 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 Sunrise, and How Can We Meet?
I do. Sunrise is an easy drive from my Fort Lauderdale office, and I have clients throughout the city. We can meet at my office, at your kitchen table, over the phone or on Zoom, whichever suits you.
Which Types of Insurance Can You Help Me With in Sunrise?
Much 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. For individuals and families I handle ACA Marketplace and off-Marketplace plans, I set up group plans for small businesses with 50 or fewer employees, and I help self-employed people find their own coverage.
I also assist people who may qualify for Extra Help, Medicare and Medicaid dual eligibility, Special Needs Plans or a Special Enrollment Period. Dental, vision, life and supplemental insurance round out the list, so your household’s coverage can be handled by one person.
How Do You Compare to Other Health Insurance Agents in Sunrise?
If you call a call center, or an agency that hands you from one person to the next, you may end up explaining your situation to someone new every time. With me, the person you speak with 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.
Many people have waited on a call-back that never arrived, reached an automated system instead of a person, or found nobody willing to help once a problem came up after enrollment. I stay involved after you enroll to help with claims and billing, and I review your coverage with you every year. I begin by asking about your health, your budget, your doctors and your prescriptions, then walk you through a full-year cost estimate for each option at whatever pace works for you.
I bring 14 years of experience, I’ve been a Top 100 HealthMarkets agent every year from 2022 through 2026, and I hold licenses in 33 states. You can verify my license (Florida License #W323530, NPN #17946070) at any time 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 Sunrise?
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 my ongoing support come at no extra cost to you. Your quote and your 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 really costs. I factor in the deductible, copays, drug costs and out-of-pocket maximum to estimate what a full year would look like for you. If you may qualify for financial help with a Marketplace plan or with Medicare prescription drug costs, I’ll go over those options with you.
Will My Plan Cover the Hospitals and Doctors I Use Near Sunrise?
That depends on the plan, because each one has its own network. Give me the names of your doctors, your preferred hospitals and your pharmacy, 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.
If you’re approaching 65, your Initial Enrollment Period is a seven-month window around your birthday, and losing job-based coverage or moving can open other windows as well. Starting early gives us time to get it right. 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.