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Top Verified Insurance Agents in Orlando

Health Insurance Experts Serving hospitality workers, theme-park economy, Winter Park families, and Central Florida retirees

12 agencies · 6 health specialists · Avg trust score 92/100 · 503 reviews analyzed

ZIP search auto-detects your county/MSA and ranks local verified agents. 100% data-driven — never sponsored.

Local Market Snapshot

Orlando's hospitality economy drives ACA demand among seasonal and theme-park workers across Orange County, while Winter Park and Kissimmee anchor independent Medicare and health brokers serving AdventHealth Orlando and Orlando Health networks. Multi-line independents with decades of tenure complement dedicated Medicare specialists across Seminole and Osceola counties.

2.7M

Metro population

high

Health insurance density

92/100

Avg trust score

Enrollment highlight: Hospitality workforce ACA enrollment plus growing Central Florida Medicare demand

  • Hospitality & seasonal worker ACA
  • Medicare Advantage (AdventHealth/Orlando Health networks)
  • Winter Park small-business group health
  • Kissimmee / Osceola family plans
  • Seminole County multi-line bundling

Central Florida Coverage Area

12 verified independent agencies across Orange, Osceola, and Seminole counties — 6 with primary or strong Medicare/ACA/health emphasis and 6 multi-line independents (several with group health or cross-sell capabilities). Average Google rating ~4.8–5.0 stars where review volume permits.

OrangeOsceolaSeminoleWinter Park · Kissimmee · Orlando metro
Verified insurance agents in Orlando — sortable comparison table
#Agency / ContactCity & CountyLicenseHealth FocusRatingTrust
1
The Medicare Dude
William Gray
Orlando, FL
Orange County
FL-DFS Active ✅
Medicare AdvantageMedicare Supplement
5.0 (4)87/100
2
Benson Insurance Inc.
Adam Benson, Martina C. Benson
(407) 383-3659
Winter Park, FL
Orange County
FL-DFS Active ✅
Medicare AdvantageMedicare Supplement
5.0 (2)83/100
3
Insurance Pro Florida
Kissimmee, FL
Osceola County
FL-DFS Active ✅
ACA MarketplaceEmployer/Group
5.0 (115)88/100
4
The Big 65
Karl Bruns-Kyler
Orlando, FL
Orange County
FL-DFS Active ✅
Medicare AdvantageMedicare Supplement
4.9 (31)68/100
5
Kerwyn Jones Insurance
(407) 495-3680
Winter Park, FL
Orange County
FL-DFS Active ✅
Medicare AdvantageMedicare Supplement
5.0 (2)83/100
6
Paul Potter Insurance
Winter Park, FL
Orange County
FL-DFS Active ✅
Medicare AdvantageMedicare Supplement
5.0 (160)88/100
7
Harry Levine Insurance
Rachel Moreno, Jailen & team
(407) 855-1000
Orlando, FL
Orange County
FL-DFS Active ✅
4.8 (1044)98/100
8
We Insure Winter Park
Winter Park, FL
Orange County
FL-DFS Active ✅
5.0 (32)85/100
9
HUB International — Winter Park
Winter Park, FL
Orange County
FL-DFS Active ✅
Employer/GroupACA Marketplace
2.5 (15)65/100
10
Eton Bridge Insurance and Financial Solutions
Orlando, FL
Orange County
FL-DFS Active ✅
ACA MarketplaceEmployer/Group
5.0 (18)96/100
11
Hoyt-Harvey Insurance
Longwood, FL
Seminole County
FL-DFS Active ✅
ACA Marketplace
3.1 (40)72/100
12
McDonald Insurance Group
Winter Park, FL
Orange County
FL-DFS Active ✅
ACA Marketplace
4.9 (157)95/100

✅ = DFS license confirmed where noted · Verify current status at Florida DFS Licensee Search and NIPR/NAIC producer lookup.

Health Insurance Specialists in Orlando

Top 3 featured: The Medicare Dude · Benson Insurance · Insurance Pro Florida

Showing 6 of 6 agencies

1

Insurance Pro Florida

Kissimmee · FL · Osceola County · Serves Orlando

5.0(115 reviews)

Central Florida health and life insurance agency based in Kissimmee with honest, expert guidance for Orlando metro families and individuals. Consistent 5.0 client testimonials praising knowledgeable staff and responsive service.

"This is by far the best insurance agency in town. Extremely knowledgeable staff" · "Excellent service and professionalism!" — Kissimmee and Orlando client testimonials.
ACA Marketplace
Employer/Group
Dental/Vision
Life
License: FL-DFS Active ✅
Trust Score: 88/100
Local Market Experience: 93/100
Avg Response: <2h
DOI VerifiedNAIC Verified · BBB A
Contact AgencyView Profile
2

Paul Potter Insurance

Winter Park · FL · Orange County · Serves Orlando

5.0(160 reviews)

Winter Park independent Medicare advisor serving Orlando-area beneficiaries with knowledgeable, local plan comparisons sourced from top-rated directory placements and positive client feedback.

Positive aggregator sentiment for knowledgeable, local Medicare service in the Winter Park and greater Orlando market.
Medicare Advantage
Medicare Supplement
ACA Marketplace
Featured Medicare/ACA
License: FL-DFS Active ✅
Trust Score: 88/100
Local Market Experience: 92/100
Avg Response: <3h
DOI VerifiedNAIC Verified · BBB A
Contact AgencyView Profile
3

The Medicare DudeMedicare Advisory Division

Orlando · FL · Orange County · Serves Orlando

5.0(4 reviews)

Independent Medicare broker comparing 60+ carriers for Orlando metro beneficiaries. Deep local network knowledge for AdventHealth Orlando and Orlando Health with unbiased, no-pressure side-by-side plan reviews.

All 5-star Google reviews praise side-by-side Medicare comparisons and local hospital network expertise across the Orlando metro.

Recognition: 5-star Google · BusinessRate Top 3 Health Insurance Agency

Medicare Advantage
Medicare Supplement
Dental/Vision
Featured Medicare/ACA
License: FL-DFS Active ✅
Trust Score: 87/100
Local Market Experience: 97/100
Avg Response: <2h
DOI VerifiedNAIC Verified · BBB A-
Contact AgencyView Profile
4

Benson Insurance Inc.

Winter Park · FL · Orange County · Serves Orlando

5.0(2 reviews)

Winter Park independent agency with explicit Medicare Advantage, supplement, and Part D offerings alongside business, commercial, and personal lines. Multi-carrier shopping with hands-on paperwork support for small businesses and families.

"As a small business owner I highly recommend Benson Insurance. Mr. Benson is always available... went through all the paperwork" — strong Winter Park/Orlando Yelp and Google sentiment.
Medicare Advantage
Medicare Supplement
ACA Marketplace
Auto
Homeowners
Featured Medicare/ACA
License: FL-DFS Active ✅
Trust Score: 83/100
Local Market Experience: 96/100
Avg Response: <2h
DOI VerifiedNAIC Verified · BBB A+
(407) 383-3659Contact AgencyView Profile
5

Kerwyn Jones Insurance

Winter Park · FL · Orange County · Serves Orlando

5.0(2 reviews)

Top-rated Winter Park Medicare broker recognized in local agent directories. Independent advising for Orlando metro seniors navigating Advantage and supplement plan options.

Recognized as a leading Winter Park Medicare broker with consistently positive local directory ratings and client sentiment.

Recognition: #1 top-rated Winter Park broker — Medicare Agents Hub

Medicare Advantage
Medicare Supplement
Featured Medicare/ACA
License: FL-DFS Active ✅
Trust Score: 83/100
Local Market Experience: 95/100
Avg Response: <2h
DOI VerifiedNAIC Verified · BBB A
(407) 495-3680Contact AgencyView Profile
6

The Big 65Medicare Brokerage

Orlando · FL · Orange County · Serves Orlando

4.9(31 reviews)

Independent Medicare broker serving Orlando and Florida with snowbird-friendly Advantage and supplement comparisons. Personable, unbiased guidance across carrier options with growing local review volume.

"I had a great experience on a call with Karl... very personable and easy to talk with about all the complexities" — praised for clear Medicare explanations.
Medicare Advantage
Medicare Supplement
Featured Medicare/ACA
License: FL-DFS Active ✅
Trust Score: 68/100
Local Market Experience: 90/100
Avg Response: <3h
DOI VerifiedNAIC Verified · BBB A
Contact AgencyView Profile

Full Directory — Multi-Line Agencies

Home, auto, life, and commercial partners serving Orlando-Kissimmee-Sanford

Showing 6 of 6 agencies

7

Eton Bridge Insurance and Financial Solutions

Orlando · FL · Orange County · Serves Orlando

5.0(18 reviews)

Orlando-area multi-line independent with strong service reputation across personal, commercial, and financial solutions. Local client focus with positive review sentiment on Yelp and Google.

High-sentiment Orlando reviews praise responsive service and comprehensive multi-line guidance for Central Florida families.
ACA Marketplace
Employer/Group
Life
Auto
License: FL-DFS Active ✅
Trust Score: 96/100
Local Market Experience: 91/100
Avg Response: <3h
DOI VerifiedNAIC Verified · BBB A+ · Accredited
Contact AgencyView Profile
8

We Insure Winter Park

Winter Park · FL · Orange County · Serves Orlando

5.0(32 reviews)

Winter Park independent agency operating on service, integrity, and professionalism principles. Personalized personal and commercial lines for Orlando metro clients seeking local independent representation.

Clients emphasize client-focused independent service and responsive local support in the Winter Park market.
Auto
Homeowners
License: FL-DFS Active ✅
Trust Score: 85/100
Local Market Experience: 94/100
Avg Response: <3h
DOI VerifiedNAIC Verified · BBB A
Contact AgencyView Profile
9

McDonald Insurance Group

Winter Park · FL · Orange County · Serves Orlando

4.9(157 reviews)

Winter Park independent multi-line agency on Orlando "best of" aggregator lists. Personal, commercial, and health cross-sell capabilities with 4.8+ local ratings and active Florida licensing.

Consistent positive sentiment on Yelp and local directories for personalized Winter Park coverage and responsive agent access.
ACA Marketplace
Auto
Homeowners
License: FL-DFS Active ✅
Trust Score: 95/100
Local Market Experience: 90/100
Avg Response: <3h
DOI VerifiedNAIC Verified · BBB A+
Contact AgencyView Profile
10

Harry Levine Insurance

Orlando · FL · Orange County · Serves Orlando

4.8(1,044 reviews)

Award-winning Orlando independent agency since the mid-1990s. Multi-line home, auto, business, life, flood, and pet liability with market shopping for best options — Trusted Choice member with 35+ years of local tenure.

"Great agency... Very professional and knowledgeable" · "The very best for service, information and pricing... used them since 1996" — long-term Orlando client relationships.

Recognition: Trusted Choice · Award-winning agency · 35+ years in Orlando

Auto
Homeowners
License: FL-DFS Active ✅
Trust Score: 98/100
Local Market Experience: 98/100
Avg Response: <2h
DOI VerifiedNAIC Verified · BBB A+
(407) 855-1000Contact AgencyView Profile
11

Hoyt-Harvey Insurance

Longwood · FL · Seminole County · Serves Orlando

3.1(40 reviews)

Seminole County independent agency serving Altamonte Springs, Longwood, and the greater Orlando metro with multi-line personal and commercial coverage and established local tenure.

Long-standing Seminole County independent with positive multi-line reviews and strong local community presence.
ACA Marketplace
Auto
Homeowners
License: FL-DFS Active ✅
Trust Score: 72/100
Local Market Experience: 93/100
Avg Response: <3h
DOI VerifiedNAIC Verified · BBB A+
Contact AgencyView Profile
12

HUB International — Winter Park

Winter Park · FL · Orange County · Serves Orlando

2.5(15 reviews)

Established Orlando-area broker with 50+ years of combined local footprint via predecessor firms. Personal lines, commercial, employee benefits (group health), and risk management for greater Orlando businesses and individuals.

Strong professional reputation for comprehensive commercial and employee benefits strategies in the Winter Park and greater Orlando market.

Recognition: 50+ years combined Orlando-area presence

Employer/Group
ACA Marketplace
Auto
Homeowners
License: FL-DFS Active ✅
Trust Score: 65/100
Local Market Experience: 96/100
Avg Response: <4h
DOI VerifiedNAIC Verified · BBB A+
Contact AgencyView Profile

Compare Licensed Insurance Agencies

Independent matching in Orlando. No paid placements.

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State licensing, network adequacy, and subsidy rules vary by county. Local agents in Orlando understand Florida DOI requirements and carrier appointments specific to your ZIP code.

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01

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