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Chaperone Health Insurance Plus

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~30 min from my office · Video calls available

Health and Medicare Insurance Agent Near You in Pembroke Pines, FL

I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, working out of Fort Lauderdale and meeting clients across Broward County. Over 14 years I’ve helped people line up health and Medicare plans side by side and choose the one that fits their doctors, their prescriptions and their budget, and I’d welcome the chance to do that for you and your family in Pembroke Pines.

I explain everything in plain English, I never push, and I remain your agent long after the paperwork is done. Book a free plan review and you’ll hear back from me 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 Pembroke Pines: What Local Residents Should Know

Pembroke Pines has two hospitals inside the city limits, Memorial Hospital West on North Flamingo Road and Memorial Hospital Pembroke on Sheridan Street, and the rest of Memorial Healthcare System is a short drive away, including Memorial Hospital Miramar and Memorial Regional Hospital in Hollywood (Memorial Healthcare System). Many residents in the western part of the city also use Cleveland Clinic Weston Hospital on Weston Road (Cleveland Clinic Florida).

Whether a given plan covers your doctors and your hospital comes down to that plan’s network, and no two networks are identical. Before I recommend anything, I run your doctors, hospitals, prescriptions and pharmacy against each plan on the table, and if a detail is unclear I pick up the phone and call your doctor’s office myself.

My office is about half an hour from Pembroke Pines, close enough that meeting face to face, getting help with a claim or a bill after you enroll, or sitting down together for your annual review is simple to arrange. I work with clients throughout Pembroke Pines, including Pembroke Falls, Chapel Trail, Silver Lakes, Grand Palms, Pembroke Shores, Pembroke Isles and Towngate. I also serve nearby Miramar, Hollywood, Cooper City, Davie, Southwest Ranches and Weston.

Pembroke Pines Driving Directions & Parking

From central or western Pembroke Pines, take Pines Boulevard to I-75 and head north to I-595. Follow I-595 east to I-95, then take I-95 north to Exit 33B (Cypress Creek Road West). If you live in the eastern part of the city, Florida’s Turnpike north to I-595 east and then I-95 north gets you to the same exit.

Once you leave the highway, 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, in the Cypress Court building.

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 and I’ll point you the right way.

Prefer to meet at home? I also make home visits throughout Pembroke Pines 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.

Pembroke Pines Health Insurance FAQ

Do You Serve Pembroke Pines, and How Can We Meet?

Yes. I work with clients in every part of Pembroke Pines, from the neighborhoods along University Drive out to the communities west of I-75. We can meet at my Fort Lauderdale office, at your home, over the phone or on Zoom, whichever is easiest for you.

What Types of Insurance Do You Help With in Pembroke Pines?

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 businesses with group plans for 50 or fewer employees, and self-employed people who need coverage of their own.

Beyond that, I assist people who may qualify for Extra Help, Medicare and Medicaid dual eligibility, Special Needs Plans or a Special Enrollment Period, and I offer dental, vision, life and supplemental insurance. That way your household’s coverage can be handled by one person who knows your situation.

How Do You Compare to Other Health Insurance Agents in Pembroke Pines?

When you call a call center, or an agency where you get handed from one person to the next, you may be starting over with someone new every time. With me, you always deal with the same person: me. You have my direct line, there is no assistant or call center in between, and I get back to you within 24 to 48 hours.

Waiting on a call-back that never arrives, reaching an automated system instead of a person, or having no one to turn to when a problem comes up after enrollment are the complaints I hear most often. I stay with you after you enroll to help with claims and billing, and I sit down with you every year to review your coverage. I begin by asking about your health, your budget, your doctors and your prescriptions, and only then do I show you a full-year cost estimate for each option, explained at whatever pace suits you.

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) 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 Pembroke Pines?

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 there is no obligation to enroll.

Keep in mind that the premium is just one piece of the picture. I add up the deductible, copays, drug costs and out-of-pocket maximum to estimate what a plan would really cost you over a full year. If you may qualify for financial help with a Marketplace plan or with Medicare prescription costs, I’ll walk you through what that could mean.

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

That depends on the plan, because every plan has its own network. Give me the names of your doctors, your preferred hospital 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 directly.

When Should I Start Looking at Plans?

Medicare’s Annual Enrollment Period for 2027 plans runs from October 15 to December 7, 2026, and any changes you make 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 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 as well. Starting early gives us time to get it right. 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.

Roxroy-Ashley-748931.webp

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.