ADVERTISING DISCLOSURE: BeforeInsuranceUSA.com is an informational directory, not an insurance agency, broker, or licensed producer. We do not sell insurance or provide insurance advice. No agent-client relationship is created by using this site. Except where a listing is clearly marked Featured, no agent listed on this site has paid for their listing. Featured listings are paid advertisements. This is an advertisement.
HomeMedicare Insurance AgentsFlorida › Winter Springs

Find Medicare Insurance Agents Near You in Winter Springs, FL

Browse medicare insurance agents serving Winter Springs, Florida. Updated 2026-07-14.

The top-rated medicare insurance agent in Winter Springs, Florida is Josh Dike - State Farm Insurance Agent, rated 4.9 stars across 349 reviews. Other highly rated options include Pontell Insurance Group, Jeremy Jones - State Farm Insurance Agent, Visitor Insurance Services of America (VISOA®). This directory lists 14 medicare insurance agents serving Winter Springs.

Showing 14 medicare insurance agents in Winter Springs, FLListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Josh Dike - State Farm Insurance Agent680 E State Rd 434(407) 890-9488
2Pontell Insurance Group1331 Sundial Point(407) 696-1333
3Jeremy Jones - State Farm Insurance Agent1049 Willa Springs Dr # 1031(407) 699-1531
4Visitor Insurance Services of America (VISOA®)1073 Willa Springs Dr STE 1009(407) 669-6400
5Sunny Insurance Agency LLC3625 FL-419 suite 290(407) 274-9674
6We Insure Winter Springs - Josh Hinkle890 Northern Way #2(321) 422-3255
7TNT Insurance Agency LLC1065 E State Rd 434(386) 310-1660
8Jean Arthur Associates Inc5626 Red Bug Lake Rd(407) 699-9930
9Soper Perez & Associates, Inc.506 E State Rd 434(407) 327-2550
10Camp Insurance Llc126 W State Rd 434(407) 544-4363
JD
680 E State Rd 434
Josh Dike - State Farm Insurance Agent
Medicare Insurance Agent · Winter Springs, FL

Josh Dike - State Farm Insurance Agent serves Winter Springs and surrounding Seminole County, Florida, as a local Medicare insurance agent. The agency helps individuals navigate Medicare plans and options available in the area. It focuses on matching clients with suitable coverage for their healthcare needs and budgets in this region. The office handles both Medicare Advantage and Medicare Supplement plan selections for local residents.

PI
1331 Sundial Point
Pontell Insurance Group
Medicare Insurance Agent · Winter Springs, FL

Pontell Insurance Group provides Medicare insurance guidance and enrollment services to individuals in Winter Springs, Florida. Its offerings include helping clients understand and select Medicare Advantage, Medicare Supplement, and Part D prescription drug plans, along with annual plan reviews to adjust coverage as healthcare needs evolve. The agency assists with navigating enrollment periods, plan comparisons, and ongoing support for claims or coverage questions. Pontell Insurance Group services single-family homes, apartments, and retail clients in the surrounding area.

JJ
1049 Willa Springs Dr # 1031
Jeremy Jones - State Farm Insurance Agent
Medicare Insurance Agent · Winter Springs, FL

Jeremy Jones - State Farm Insurance Agent in Winter Springs, FL serves homeowners, retirees, and individuals navigating Medicare enrollment. The agency provides guidance on Medicare Supplement and Advantage plans, helping clients select coverage that fits their healthcare needs and budgets. With personalized appointments, the agent explains plan options, eligibility timelines, and prescription drug coverage. This local office also assists residents in Oviedo with their Medicare insurance questions and plan selections.

VI
1073 Willa Springs Dr STE 1009
Visitor Insurance Services of America (VISOA®)
Medicare Insurance Agent · Winter Springs, FL

Serving the Winter Springs area and surrounding Central Florida communities, Visitor Insurance Services of America (VISOA®) handles Medicare insurance needs, including plan options and enrollment guidance. As a Medicare insurance agent, it assists clients in navigating supplement and Advantage plans available in the region. To handle a typical job, it assesses an individual’s specific coverage needs and walks them through available plan choices to find a suitable match.

SI
3625 FL-419 suite 290
Sunny Insurance Agency LLC
Medicare Insurance Agent · Winter Springs, FL

Clients choosing Medicare coverage may select a one-time plan review or continue with ongoing policy adjustments. Sunny Insurance Agency LLC, serving Winter Springs, helps consumers compare plans each Annual Enrollment Period and handles Original Medicare or Medicare Advantage options. An agent explains prescription drug plans, out-of-pocket limits, and changing provider networks at each appointment. Scheduling runs on either a one-time basis for new enrollments or as a seasonal, as-needed re-evaluation each fall during Open Enrollment.

WI
890 Northern Way #2
We Insure Winter Springs - Josh Hinkle
Medicare Insurance Agent · Winter Springs, FL

We Insure Winter Springs - Josh Hinkle specializes in helping clients navigate Medicare plans, including supplements and prescription drug coverage, to match individual health needs. The agency provides personalized consultations throughout Winter Springs, Florida, to explain plan options and enrollment procedures clearly. It assists with annual reviews to ensure coverage remains appropriate and effective. Seasonal support is offered during the Annual Enrollment Period when beneficiaries may adjust their plans due to changing health conditions or prescription requirements.

TI
1065 E State Rd 434
TNT Insurance Agency LLC
Medicare Insurance Agent · Winter Springs, FL

As local Medicare enrollment periods bring new questions each year, TNT Insurance Agency LLC in Winter Springs, FL provides guidance on available plans and coverage options. Their representatives work with clients to evaluate current healthcare needs, explain Medicare parts and supplements, and clarify how different policies apply to prescriptions or doctor choices. Each initial meeting focuses on a careful review of the individual’s existing coverage and medical requirements. That first consultation typically includes a plan comparison to identify the most suitable choices for the season.

JA
5626 Red Bug Lake Rd
Jean Arthur Associates Inc
Medicare Insurance Agent · Winter Springs, FL

Jean Arthur Associates Inc works with individuals throughout Winter Springs, FL, to navigate their medicare insurance options. The agency specializes in helping clients select appropriate supplemental plans and prescription drug coverage. Medicare insurance agents in this area assist with annual enrollment periods and plan comparisons. The company serves various commercial sectors in the local region, including administrative offices, retail warehouses, and food service establishments.

SP
506 E State Rd 434
Soper Perez & Associates, Inc.
Medicare Insurance Agent · Winter Springs, FL

Soper Perez & Associates, Inc., based in Winter Springs, FL, is a medicare insurance agent. The firm assists clients throughout the region with navigating medicare plan options, including Advantage and Supplement plans. It also guides individuals through enrollment periods and plan changes to match their unique healthcare needs. For those requiring additional coverage, the agency can help arrange stand-alone Prescription Drug Plan options.

CI
126 W State Rd 434
Camp Insurance Llc
Medicare Insurance Agent · Winter Springs, FL

Camp Insurance Llc serves residents in the Winter Springs, FL area with guidance through Medicare insurance options. The agency also assists businesses in the region by addressing commercial coverage needs for their employees. Agents help clients understand plan details, eligibility, and enrollment periods. They work with individuals to compare available policies and find suitable coverage. After initial enrollment, the team follows up with clients regularly and provides ongoing support for any coverage changes or questions between annual enrollment periods.

TC
200 FL-434
True Care Insurance Agency
Medicare Insurance Agent · Winter Springs, FL
(321) 209-6082
FB
142 W State Rd 434
Farm Bureau Insurance
Medicare Insurance Agent · Winter Springs, FL
(407) 327-8749
floridafarmbureau.com
EI
1073 Willa Springs Dr #2009
Edison Insurance Services
Medicare Insurance Agent · Winter Springs, FL
(407) 359-0640
edisoninsuranceservices.com
TW
676 Blenheim Loop
Tom Wall Jr LLC
Medicare Insurance Agent · Winter Springs, FL
(407) 765-2814
myuhcagent.com/thomas-wall

What Does a a Medicare Insurance Agent in Winter Springs Cost?

Medicare insurance agent services in Florida are generally free to you because agents earn commissions from insurance carriers. Plan premiums vary: Medicare Part B costs $174.70 per month in 2024 for most people, while Medicare Advantage plans can have $0 monthly premiums but may include copays. Medigap plans in Florida range from about $100 to $400 per month depending on age and plan type. This is general information, not insurance advice.

About medicare insurance agents in Winter Springs

Medicare insurance agents in Winter Springs, Florida help residents navigate Original Medicare, Medicare Advantage, and Part D drug plans. Florida law requires agents to be licensed and to follow state regulations on marketing and enrollment. Local agents can explain how Winter Springs medical facilities and providers work with different plans.

Frequently Asked Questions

What does a Medicare insurance agent in Winter Springs do?

A Medicare insurance agent helps you compare plans, enroll in Medicare Part A and Part B, and choose a Medicare Advantage or Medigap policy. They also assist with annual enrollment periods and special enrollment periods under Florida law.

Do I have to pay for a Medicare insurance agent in Florida?

Most Medicare insurance agents in Florida are paid by insurance companies through commissions, so you typically pay no direct fee for their services. Always confirm the agents compensation structure before working with them.

When can I enroll in Medicare in Winter Springs Florida?

Your Initial Enrollment Period starts three months before you turn 65 and lasts for seven months. Florida also has an Annual Enrollment Period from October 15 to December 7 for plan changes. Special Enrollment Periods may apply if you move or lose other coverage.

Medicare Insurance Agents in Other Florida Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each medicare insurance agent's credentials and current standing with your state Department of Insurance.