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Chaperone Health Insurance Plus

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~20 min from my office · Video calls available

Health and Medicare Insurance Agent Near You in Hollywood, FL

I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, and my office is in Fort Lauderdale, a straight run up I-95 from Hollywood. Over 14 years I’ve helped more than 1,800 people compare health and Medicare plans side by side, starting with their doctors, their prescriptions and their budget, and I’d be glad to do the same for you and your family in Hollywood.

I explain everything in plain language, I never pressure anyone to sign, and once you enroll I remain your agent for claims, billing and your yearly review. Book a free plan review and I’ll get back to you personally within 24 to 48 hours.

No cost. No obligation to enroll.

Florida License #W323530   •   NPN #17946070   •   AHIP certified for the 2027 plan year   •   Registered with the federal Marketplace

14

Years in Insurance

1,800+

Clients Helped

85%+

Client Retention

Top 100

HealthMarkets Agent, 2022–2026

MORE THAN A FREE QUOTE​

Independent Health, Medicare & Life Insurance Broker

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.

  • Your Doctors and Prescriptions Checked: I confirm your providers, medications, and pharmacy are covered before recommending any plan. If something is unclear, I’ll call your doctor’s office myself.
  • The Plan That Costs Less for You: The lowest premium isn’t always the lowest cost. I calculate your full-year cost for every plan, based on your doctors, prescriptions, and health needs, before you choose.
  • Expert Help, Free to You: My reviews and enrollment help are free. Insurers pay my commission, and premiums are generally the same whether you use an agent or not.
  • At Your Pace, Every Question Answered: I’ll walk you through your options at your pace, answer every question, and let you decide what’s right. There’s no obligation to enroll.
  • I Handle the Paperwork: If you choose a plan, I complete the application with you and follow it through to approval, so the process is as simple as a conversation.
  • I Stay Your Agent After You Enroll: Work with me directly, in person, by phone, or on Zoom, and I reply within 24 to 48 hours, for annual reviews, claims, and every change in between.
  • Coverage for Every Stage of Life: Medicare, ACA/Marketplace Health Insurance, Small Business Plans, Life, Dental, Vision, and Supplemental Coverage.

Hear how I help you choose a plan with confidence.

CLIENT REVIEWS

What my clients say

"An Outstanding Insurance Agent Who Truly Cares!"

Roxroy is an exceptional insurance agent, and I couldn’t be happier with the service he provides. He takes such good care of both my mom and me, making sure our insurance needs are handled with care, attention, and professionalism.
 
It’s such a relief to have someone you can trust who genuinely looks out for you and your family. Roxroy goes above and beyond to make sure we’re taken care of, and that kind of personal attention means so much to us.
 
I truly appreciate everything he does and highly recommend him to anyone looking for an insurance agent who is knowledgeable, dependable, and genuinely cares about his clients!

"Roxroy is a miracle worker!"

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)

DOCTORS, HOSPITALS & NETWORKS

Health Insurance in Hollywood: What Local Residents Should Know

Hollywood is the home base of Memorial Healthcare System, with Memorial Regional Hospital on Johnson Street, Memorial Regional Hospital South on Washington Street and Joe DiMaggio Children’s Hospital all inside the city, and Memorial Hospital Pembroke and Memorial Hospital West a short drive west in Pembroke Pines (Memorial Healthcare System locations).

Having good hospitals nearby only helps if your plan’s network includes the doctors you actually see. Networks differ from one plan to the next, so before I recommend anything I run your doctors, hospitals, prescriptions and pharmacy against each plan we’re considering, and if a listing looks unclear I pick up the phone and call your doctor’s office to confirm.

Because my office is one exit-to-exit drive up I-95 from Hollywood, 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 each year to review your coverage. I work with clients in neighborhoods across the city, including Hollywood Lakes, Hollywood Hills, Emerald Hills, Hillcrest, Driftwood, Boulevard Heights and Liberia. I also serve nearby Hallandale Beach, Dania Beach, Pembroke Pines, Miramar, West Park and Davie.

Hollywood Driving Directions & Parking

From Downtown Hollywood or the beach, take Hollywood Boulevard west to I-95 and head north about 13 miles to Exit 33B (Cypress Creek Road West). If you’re in western Hollywood, Sheridan Street or Pines Boulevard east to I-95 north gets you onto the same route.

At the exit, continue west on Cypress Creek Road for a few blocks, then turn right (north) 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 anything is hard to find, call me at 954-410-3710 and I’ll walk you in.

Prefer to meet at home? I also make home visits throughout Hollywood and the rest of Broward County.

Cities I Serve in 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.

Hollywood Health Insurance FAQ

Do You Serve Hollywood, and Where Can We Meet?

Yes. I work with clients throughout Hollywood, from the beach to the neighborhoods west of I-95. We can meet at my Fort Lauderdale office, at your home, over the phone or on Zoom, whichever suits you.

Which Types of Insurance Do You Help Hollywood Residents With?

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. 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 their own coverage.

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. Dental, vision, life and supplemental insurance are available too, so one person can look after all of your family’s coverage.

How Do You Compare to Other Health Insurance Agents in Hollywood?

At a call center, or at an agency where you’re handed from one person to the next, you may speak with someone new every time you call. With me, you always work with the same person: 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 had an agent who was hard to reach, promised a call-back that never came, or disappeared after enrollment, and some have only ever reached an automated phone system. I do it differently. I stay on after you enroll to help with claims and billing, I review your coverage with you every year, and I begin by asking about your health, your budget, your doctors and your prescriptions before I suggest a single plan. Then I lay out a full-year cost estimate for each option and go through it at your pace.

I bring 14 years in insurance, with the last 8 focused on Medicare, and I’ve been named a Top 100 HealthMarkets agent every year from 2022 through 2026. I’m licensed in 33 states, and my license (Florida License #W323530, NPN #17946070) can be verified 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 Hollywood?

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 there is no obligation to enroll.

Keep in mind that the premium is only one piece of what you’ll actually spend. I add up the deductible, copays, drug costs and out-of-pocket maximum to give you a full-year cost estimate for each plan. If you may qualify for financial help with a Marketplace plan or with Medicare prescription drug costs, I’ll explain what that could mean for you.

Will My Plan Cover the Hospitals and Doctors I Use in Hollywood?

That depends on the plan, because every plan has its own network. Give me the names of your doctors, your hospitals and your pharmacy, and I’ll check each one against every plan we compare. If anything needs confirming, I’ll call your doctor’s office myself.

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 begins November 1, 2026, and you need to enroll by December 15, 2026 for coverage that starts January 1, 2027.

If you’re turning 65, your Initial Enrollment Period is a seven-month window around your birthday, and losing job-based coverage or moving can open a Special Enrollment Period at other times of the year. Starting early gives us time to compare carefully, so get your free quote and I’ll help you pin down your dates.

A Bit More About Me

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.

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Book a Free Plan Review

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.

Roxroy Ashley - Licensed Insurance Agent

How we'll work together

Five steps, no pressure, and I stay with you after you enroll.

 

1

We talk about you

By phone, Zoom or face to face. Your health, your budget, your doctors.

2

I check the details

Doctors, hospitals, prescriptions and pharmacy, checked against each plan.

3

We compare real costs

A full-year estimate for each option, explained in plain language.

4

You decide, I enroll you

No pressure. If you choose a plan, I handle the application with you.

5

We review every year

Plans and networks change. I check yours each year and help with claims in between.