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Chaperone Health Insurance Plus

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~15 min from my office · Video calls available

Health and Medicare Insurance Agent Near You in Deerfield Beach, FL

I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, with my office in Fort Lauderdale. Over the past 14 years I’ve helped people weigh health and Medicare plans side by side, starting from their doctors, their prescriptions and what they can comfortably spend, and I’d be glad to do that for you and your family in Deerfield Beach.

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 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 Deerfield Beach: What Local Residents Should Know

Deerfield Beach has a hospital inside the city limits, Broward Health North on East Sample Road, and several more a short drive away, including Broward Health Imperial Point in Fort Lauderdale, HCA Florida Northwest Hospital in Margate and Boca Raton Regional Hospital, part of Baptist Health, just across the county line in Boca Raton (Broward Health North, Broward Health Imperial Point, HCA Florida Northwest, Boca Raton Regional Hospital).

Whether a plan covers the doctors and hospitals you rely on comes down to its network, and every network is different. Before I recommend anything, I run your doctors, hospitals, prescriptions and pharmacy against each plan we’re considering, and if something isn’t clear I pick up the phone and call your doctor’s office myself.

Because my office is only a short drive down I-95 from Deerfield Beach, 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 all over Deerfield Beach, including The Cove, Deer Creek, Crystal Lake, Century Village, Carver Heights, Tedder and Hillsboro Ranches. I also serve nearby Pompano Beach, Lighthouse Point, Hillsboro Beach, Coconut Creek and Boca Raton.

Deerfield Beach Driving Directions & Parking

From Deerfield Beach, take Hillsboro Boulevard west to I-95 and head south about nine miles to Exit 33B (Cypress Creek Road West). If you’re coming from the Sample Road area or western Deerfield Beach, Sample Road to I-95 south, or Powerline Road straight south to Cypress Creek Road, gets you here just as easily.

From the exit, go west on Cypress Creek Road a few blocks and 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 you have any trouble finding it, call me at 954-410-3710.

Prefer to meet at home? I also make home visits throughout Deerfield Beach 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.

Deerfield Beach Health Insurance FAQ

Do You Work With Clients in Deerfield Beach, and How Can We Meet?

Yes. Deerfield Beach is a quick trip up I-95 from my Fort Lauderdale office, and I have clients throughout the city. We can meet at my office, at your home, over the phone or on Zoom, whichever suits you.

What Kinds of Coverage Can You Help With in Deerfield Beach?

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.

Beyond that, I help 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 are available too, so your family’s coverage can all be handled by one person.

How Do You Compare to Other Health Insurance Agents in Deerfield Beach?

At a call center, or at an agency where you’re handed 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’s no assistant or call center in between, and I reply within 24 to 48 hours.

Call-backs that never arrive, a phone answered by an automated system, or an agent who disappears once the paperwork is signed are common complaints, and I’ve built my practice around avoiding them. I stay involved after enrollment 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 your pace.

I bring 14 years of experience, 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 Deerfield Beach?

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 go directly to 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 just one piece of what a plan really costs. I add up the deductible, copays, drug costs and out-of-pocket maximum to estimate your true cost for the whole year. 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.

Which Deerfield Beach Hospitals and Doctors Will My Plan Cover?

That depends on the plan, because each one has its own network. Give me the names of your doctors, your preferred hospital and your pharmacy, and I’ll check them 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 take effect January 1, 2027. For ACA Marketplace coverage, Open Enrollment for 2027 plans begins 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 enrollment windows as well. It pays to start early. Get your free quote and I’ll help you pin down the dates that apply to you.

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.