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Find Medicare Insurance Agents Near You in Oldsmar, FL

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

The top-rated medicare insurance agent in Oldsmar, Florida is Freeway Insurance, rated 5.0 stars across 246 reviews. Other highly rated options include Brightway Insurance - The Dittman Agency, We Insure Oldsmar - Edison Debarros, Freddy Alfaro-Aprendiendo de Seguros. This directory lists 10 medicare insurance agents serving Oldsmar.

Showing 10 medicare insurance agents in Oldsmar, FLListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Freeway Insurance127 Forest Lakes Blvd Ste 5(727) 203-7012
2Brightway Insurance - The Dittman Agency3705 Tampa Rd UNIT 1(727) 493-0918
3We Insure Oldsmar - Edison Debarros501 St Petersburg Dr E Ste A(727) 614-2424
4Freddy Alfaro-Aprendiendo de Seguros327 Lake Placid Ct(813) 358-7064
5Stephen Belau - State Farm Insurance Agent3730 Tampa Rd #2(813) 343-0926
6Florida West Insurance Inc3800 Tampa Rd #140(813) 886-4446
7Stahl & Associates Insurance3939 Tampa Rd #1(813) 818-5300
8Barber Agency, Inc.3902 Tampa Rd(727) 726-1112
9STAR NSURANCE180 N Race Track Rd(954) 287-1512
10Hospitality Insurance Agency4025 Tampa Rd(727) 726-1112
FI
127 Forest Lakes Blvd Ste 5
Freeway Insurance
Medicare Insurance Agent · Oldsmar, FL

As Florida’s open enrollment season approaches, residents of Oldsmar often face complex decisions about their prescription drug coverage and supplemental plans. Freeway Insurance, a dedicated Medicare Insurance Agent in the area, helps local seniors navigate these annual changes to find a plan that fits their health needs and budget. During an initial consultation, agents review each client’s current medications, preferred doctors, and monthly costs. They then compare available Medicare Advantage or Part D options before scheduling an in-person or virtual inspection of the individual’s coverage requirements.

BI
3705 Tampa Rd UNIT 1
Brightway Insurance - The Dittman Agency
Medicare Insurance Agent · Oldsmar, FL

Brightway Insurance - The Dittman Agency serves the Tampa Bay area and Hillsborough County from its base in Oldsmar, Florida. As a Medicare insurance agent, the agency helps clients navigate their coverage options during enrollment periods. It provides guidance on selecting plans that suit individual healthcare needs and budgets. The agency specializes in assisting with Medicare Supplement plans and Medicare Advantage policies for local residents.

WI
501 St Petersburg Dr E Ste A
We Insure Oldsmar - Edison Debarros
Medicare Insurance Agent · Oldsmar, FL

We Insure Oldsmar - Edison Debarros provides Medicare insurance guidance, including plan comparisons and annual enrollment assistance. The agency helps clients evaluate Medicare Advantage, Supplement, and Part D drug options to match healthcare needs and budgets. It offers ongoing policy reviews to ensure coverage remains appropriate as circumstances change. The service area includes single-family homes, apartments, and retail clients in Oldsmar, Florida.

FA
327 Lake Placid Ct
Freddy Alfaro-Aprendiendo de Seguros
Medicare Insurance Agent · Oldsmar, FL

Homeowners and retirees in Oldsmar, FL, seeking Medicare guidance can turn to Freddy Alfaro-Aprendiendo de Seguros, a Medicare insurance agency. The company offers education and enrollment assistance for Medicare plans, helping clients understand their coverage options. Services include comparing plans, navigating enrollment periods, and explaining benefits. The agency also serves the greater Tampa Bay metro area, including neighboring communities such as Safety Harbor and Clearwater.

SB
3730 Tampa Rd #2
Stephen Belau - State Farm Insurance Agent
Medicare Insurance Agent · Oldsmar, FL

Serving Oldsmar, Florida, and the surrounding Tampa Bay communities, Stephen Belau as a State Farm Insurance Agent handles Medicare insurance plans for eligible residents. The agency assists clients in reviewing their coverage options during enrollment periods. A typical job involves helping individuals compare plan benefits and costs to find a suitable policy. Stephen Belau uses a thorough consultation to explain how different plans work with their existing healthcare needs.

FW
3800 Tampa Rd #140
Florida West Insurance Inc
Medicare Insurance Agent · Oldsmar, FL

Florida West Insurance Inc in Oldsmar, FL helps clients distinguish between one-time enrollment options and ongoing plan management when selecting Medicare coverage. They assist with understanding Part A and Part B benefits, Medicare Advantage plans, and prescription drug options. Yearly plan reviews and updates ensure coverage aligns with changing health needs and regulations. Their services are available on a scheduled basis, typically at the client's request for annual review periods.

SA
3939 Tampa Rd #1
Stahl & Associates Insurance
Medicare Insurance Agent · Oldsmar, FL

Stahl & Associates Insurance, located in Oldsmar, Florida, provides guidance to individuals navigating Medicare insurance options. The company assists clients in understanding the complexities of Original Medicare, Medicare Advantage, and Part D prescription drug plans, helping them select suitable coverage for their healthcare needs. As a Medicare insurance agent, the firm helps retirees and those approaching eligibility age find appropriate plans within their budget. Stahl & Associates Insurance serves both private residences and commercial sectors, including professional offices, warehouses, and food service establishments.

BA
3902 Tampa Rd
Barber Agency, Inc.
Medicare Insurance Agent · Oldsmar, FL

Barber Agency, Inc. in Oldsmar, FL, focuses on helping individuals navigate Medicare supplement and Advantage plan options, offering guidance to match coverage with healthcare needs. It further assists clients by reviewing Part D prescription drug selections and explaining enrollment procedures for those first qualifying for Medicare. This local agency also helps people facing the annual Medicare Open Enrollment Period, ensuring they understand how to adjust their plans before the December 7 deadline if their medications or budgets change.

SN
180 N Race Track Rd
STAR NSURANCE
Medicare Insurance Agent · Oldsmar, FL

With the annual Medicare open enrollment season approaching in Oldsmar, STAR NSURANCE helps local residents navigate their plan options for the coming year. This agency focuses on matching individuals with suitable Medicare Advantage or Supplement policies that fit their healthcare needs and budget. The agent takes time to explain how different plans cover prescriptions and doctor visits common in the Tampa Bay area. An initial no-obligation consultation is scheduled to review the client’s current coverage and personal medical requirements.

HI
4025 Tampa Rd
Hospitality Insurance Agency
Medicare Insurance Agent · Oldsmar, FL

Hospitality Insurance Agency provides guidance for individuals navigating Medicare coverage options in Oldsmar, Florida. The company specializes in explaining Medicare plans, including supplements and prescription drug add-ons, to help clients secure appropriate health benefits. Service focuses on understanding local healthcare needs and assisting with annual enrollment decisions. The agency also serves commercial sectors such as offices, warehouses, and food service locations within the community.

What Does a a Medicare Insurance Agent in Oldsmar Cost?

Medicare insurance agents in Florida typically do not charge a fee for their services. They are paid by the insurance carriers whose plans they sell. Plan premiums vary widely; for example, Medicare Advantage plans can have $0 monthly premiums, while Medigap plans may cost $100 to $300 per month depending on your age and location. This is general information, not insurance advice.

About medicare insurance agents in Oldsmar

Medicare insurance agents in Oldsmar, Florida help residents compare plans and enroll in Medicare Part A, Part B, Part D, and Medicare Advantage. Florida law requires agents to be licensed by the state and follow strict marketing guidelines. Agents can assist during Initial Enrollment Periods and Special Enrollment Periods based on your circumstances.

Frequently Asked Questions

What does a Medicare insurance agent in Oldsmar do?

A Medicare insurance agent helps you review plan options, explain coverage differences, and complete enrollment. They work with multiple carriers to find a plan that fits your health needs and budget.

When can I enroll in Medicare in Oldsmar Florida?

Your Initial Enrollment Period starts three months before you turn 65 and ends three months after your birthday month. In Florida, you may also qualify for a Special Enrollment Period if you move or lose other coverage.

Is there a penalty for late enrollment in Florida?

Yes. If you do not sign up for Medicare Part B when first eligible, you may pay a late enrollment penalty of 10% for each full 12-month period you delay. This penalty applies for as long as you have Part B.

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.