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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 Weston, FL

I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, based in Fort Lauderdale. Over the past 14 years I’ve helped more than 1,800 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 Weston.

I explain everything in plain language, I never rush a decision, and once you enroll I stay on as your agent for the long run. 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 Weston: What Local Residents Should Know

Weston has a major hospital inside the city limits, Cleveland Clinic Weston Hospital on Weston Road, and several more a short drive away, including HCA Florida University Hospital in Davie, HCA Florida Westside Hospital in Plantation, and Memorial Hospital West in Pembroke Pines and Memorial Hospital Miramar, both part of Memorial Healthcare System (Cleveland Clinic Weston, HCA Florida University Hospital, HCA Florida Westside Hospital, Memorial Healthcare System).

Having good hospitals nearby is one thing; knowing which ones your plan actually covers is another, because every plan has its own network. Before I recommend anything, I check 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.

Weston is an easy drive from my office along I-595 and I-95, so you can meet me in person, get help with claims and billing after you enroll, and sit down with me for your annual coverage review. I work with clients across Weston, including Bonaventure, Savanna, Weston Hills, The Ridges, Isles at Weston, Country Isles and Windmill Ranch. I also serve nearby Davie, Sunrise, Southwest Ranches, Cooper City, Pembroke Pines and Plantation.

Weston Driving Directions & Parking

From Weston, take Royal Palm Boulevard or Weston Road to I-75 and merge onto I-595 east. Stay on I-595 past Florida’s Turnpike to I-95 and take I-95 north to Exit 33B (Cypress Creek Road West). If you’re coming from Bonaventure, State Road 84 east to I-595 gets you to the same place.

From the exit, continue west on Cypress Creek Road a few blocks, then 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, 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, give me a call at 954-410-3710.

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

Weston Health Insurance FAQ

Do You Serve Weston, and How Can We Meet?

Yes. I work with clients throughout Weston, from Bonaventure to the southern end of the city. We can meet at my Fort Lauderdale office, at your home in Weston, over the phone or on a Zoom video call, whichever is most convenient for you.

Which Types of Insurance Do You Help With in Weston?

A large share 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 coverage for 50 or fewer employees, and self-employed people who need a plan 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. Dental, vision, life and supplemental insurance round out the list, so your household’s coverage can be handled by one person who knows your situation.

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

If you call a call center, or an agency that hands clients from one person to the next, you may end up explaining your situation to someone new every time. 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 the paperwork was signed. I do things differently. I help with claims and billing after you enroll and I review your coverage with you every year. I also start 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 own pace.

I bring 14 years in insurance, the last eight 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 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 Weston?

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 plan review are free, and you’re under no obligation to enroll.

Keep in mind that the premium is only the starting point. To estimate what a plan will really cost you over a year, I look at the deductible, copays, drug costs and out-of-pocket maximum together. If you may qualify for financial help with a Marketplace plan or with Medicare prescription drug costs, I’ll go over what that could mean for you.

Will My Plan Cover the Hospitals and Doctors I Use Near Weston?

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 is uncertain, I’ll call your doctor’s office to confirm before you decide.

When Should Weston Residents 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.

Turning 65 opens a seven-month Initial Enrollment Period around your birthday, and events like losing job-based coverage or moving may qualify you for a Special Enrollment Period. 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.

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.