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Chaperone Health Insurance Plus

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~25 min from my office · Video calls available

Health and Medicare Insurance Agent Near You in Cooper City, FL

I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, based in Fort Lauderdale. Over 14 years in insurance, I’ve helped more than 1,800 people compare health and Medicare plans side by side, matched to their doctors, their prescriptions and their budget, and I’d be glad to do the same for you and your family in Cooper City.

I explain everything in plain language, there’s never any pressure, and I remain your agent long after you enroll. Book a free plan review and I’ll personally reply 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 Cooper City: What Local Residents Should Know

Cooper City sits within easy reach of several hospitals. Memorial Hospital West and Memorial Hospital Pembroke are both in neighboring Pembroke Pines, and Memorial Regional Hospital is in Hollywood (Memorial Healthcare System). HCA Florida University Hospital is on South University Drive in Davie (HCA Florida University Hospital), and Cleveland Clinic Weston Hospital is a short drive west on Weston Road (Cleveland Clinic Weston).

Whether a plan covers your particular doctors and hospitals comes down to its network, and every network is different. So before I recommend anything, I check your doctors, hospitals, prescriptions and pharmacy against each plan we look at, and if a detail is unclear I call your doctor’s office myself to confirm it.

My office is an easy drive from Cooper City, which makes meeting in person simple, and the same goes for help with claims and billing after you enroll or your annual coverage review. I work with clients across Cooper City, including Embassy Lakes, Rock Creek, Monterra, Country Address, Cooper Colony Estates, Flamingo Gardens and Timberlake. I also serve nearby Davie, Pembroke Pines, Southwest Ranches, Weston and Hollywood.

Cooper City Driving Directions & Parking

From Cooper City, take Palm Avenue or Pine Island Road north to I-595 and head east toward Fort Lauderdale. Merge onto I-95 north and continue to Exit 33B (Cypress Creek Road West). If you’re in the eastern part of the city, Stirling Road or Sheridan Street east to I-95 north gets you there too.

From the exit, go west on Cypress Creek Road a few blocks and turn right onto NW 5th Way. My office is at 6360 NW 5th Way, Suite 101, Fort Lauderdale, FL 33309, just west of I-95 between Powerline Road and N Andrews Avenue.

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 Cooper City 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.

Cooper City Health Insurance FAQ

Do You Work With Clients in Cooper City, and How Can We Meet?

Yes. I work with clients throughout Cooper City, and you can choose how we meet: at my Fort Lauderdale office, at your home, by phone or over Zoom. Whichever you prefer, you’ll be working with me directly.

What Kinds of Coverage Can You Help With in Cooper City?

Much of my work is Medicare: Medicare Advantage, Medicare Supplement (Medigap) and Part D prescription drug plans, along with guidance when you’re 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 family’s coverage can all be handled in one place.

How Do You Compare to Other Health Insurance Agents in Cooper City?

With a call center, or an agency that passes you from one person to the next, you may end up speaking with someone new every time you call. With me, you always work with the same person: me. You have my direct line, there are no hand-offs to an assistant or call center, and I reply within 24 to 48 hours.

Waiting for a call-back that never arrives, or having nobody to turn to when a billing problem appears months after enrollment, is a common complaint. I stay on as your agent 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, then show you a full-year cost estimate for each option and explain it at your pace.

I bring 14 years of experience, I’ve been 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) anytime 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 Cooper City?

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 ongoing support 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 really costs. I also look at the deductible, copays, drug costs and out-of-pocket maximum so you can see an estimate of your true cost for the year. 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.

Which Cooper City Hospitals and Doctors Will My Plan Cover?

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

When Should I Get Started?

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 turning 65, your Initial Enrollment Period is a seven-month window around your birthday month, 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 confirm 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.