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HomeMedicare Insurance AgentsFlorida › Winter Garden

Find Medicare Insurance Agents Near You in Winter Garden, FL

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

The top-rated medicare insurance agent in Winter Garden, Florida is Bryan Fifer - State Farm Insurance Agent, rated 5.0 stars across 1,098 reviews. Other highly rated options include Shannon Till - State Farm Insurance Agent, Blake Price - State Farm Insurance Agent, Craig Martin - State Farm Insurance Agent. This directory lists 19 medicare insurance agents serving Winter Garden.

Showing 19 medicare insurance agents in Winter Garden, FLListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Bryan Fifer - State Farm Insurance Agent3724 Winter Garden Vineland Rd(407) 614-2622
2Shannon Till - State Farm Insurance Agent1620 Daniels Rd #110(407) 656-4000
3Blake Price - State Farm Insurance Agent14230 W Colonial Dr Suite 110(407) 573-6666
4Craig Martin - State Farm Insurance Agent14416 Shoreside Way #140(407) 656-1040
5Heather Thies - State Farm Insurance Agent15835 Shaddock Dr #150(407) 354-1320
6Shane Swan - State Farm Insurance Agent14416 Shoreside Way Suite 140(407) 452-0124
7Joseph Ferrara Insurance Services, Inc.1442 Roxy Ln(800) 930-7006
8NL Insurance Solutions Inc13640 W Colonial Dr ste 150(407) 654-6500
9Fabio Motta - Life and Health Insurance15000 Stratus Lp(407) 462-6796
10Central Florida Insurance Advisors213 S Dillard St(352) 575-2342
BF
3724 Winter Garden Vineland Rd
Bryan Fifer - State Farm Insurance Agent
Medicare Insurance Agent · Winter Garden, FL

Bryan Fifer - State Farm Insurance Agent provides a range of Medicare insurance agency services in Winter Garden, FL, including plan education and annual enrollment support. The office offers ongoing maintenance plans to help clients review their current coverage and adjust policies during open enrollment periods. Service plans focus on assisting with plan comparisons and paperwork for prescription drug coverage. The agent services individual clients, particularly those transitioning to Medicare, as well as households in single-family homes and apartment communities across the area.

ST
1620 Daniels Rd #110
Shannon Till - State Farm Insurance Agent
Medicare Insurance Agent · Winter Garden, FL

Shannon Till - State Farm Insurance Agent serves the Winter Garden, Florida area and provides medicare insurance agent services. The agency assists individuals with understanding their coverage options. Medicare insurance agents help clients navigate enrollment periods and plan specifics. They work with both Original Medicare and Medicare Advantage. The agency also handles Medicare Supplement plans. These services guide seniors and eligible residents through their insurance choices.

BP
14230 W Colonial Dr Suite 110
Blake Price - State Farm Insurance Agent
Medicare Insurance Agent · Winter Garden, FL

Blake Price - State Farm Insurance Agent in Winter Garden serves local homeowners and individuals seeking guidance on their health coverage needs. The agency provides personalized support, helping customers navigate Medicare insurance options to find a plan that fits their medical requirements and budget. Clients can expect clear explanations of parts, plans, and enrollment periods without pressure or confusion. The agency also regularly assists residents in nearby Ocoee and the surrounding southwest Orlando metro area.

CM
14416 Shoreside Way #140
Craig Martin - State Farm Insurance Agent
Medicare Insurance Agent · Winter Garden, FL

Serving Winter Garden and the surrounding communities of west Orange County, this agency handles Medicare insurance plan options for eligible individuals. It assists with enrollment, plan comparisons, and understanding coverage changes throughout the year. Clients typically receive guidance on Part A, Part B, and supplemental policies to match their healthcare needs and budget. The agent first reviews a client’s current coverage and medical usage, then presents suitable carriers and plan details, and completes the enrollment paperwork alongside the client.

HT
15835 Shaddock Dr #150
Heather Thies - State Farm Insurance Agent
Medicare Insurance Agent · Winter Garden, FL

For a one-time review, Heather Thies – State Farm Insurance Agent helps clients compare Medicare plans and select suitable coverage. Ongoing service is also available for enrollees needing assistance with annual plan changes or claim questions. Medicare insurance guidance in the Winter Garden, FL area covers both initial enrollment periods and long-term plan adjustments. These complementary options ensure policyholders understand their benefits and costs. Service is available on either a one-time, scheduled, or as-needed basis.

SS
14416 Shoreside Way Suite 140
Shane Swan - State Farm Insurance Agent
Medicare Insurance Agent · Winter Garden, FL

Shane Swan’s agency offers personalized Medicare insurance guidance for seniors in Winter Garden, helping clients evaluate supplement plans and Part D drug coverage throughout the annual enrollment period. The agency serves local residents who need to compare their options and navigate plan changes for the coming year with clarity. It assists customers with reviewing existing policies to avoid late-enrollment penalties before the Medicare open enrollment window closes each December.

JF
1442 Roxy Ln
Joseph Ferrara Insurance Services, Inc.
Medicare Insurance Agent · Winter Garden, FL

During the Medicare Annual Enrollment Period, many Central Florida retirees seek clear guidance on their coverage options. Joseph Ferrara Insurance Services, Inc. in Winter Garden, Florida, helps seniors compare Medicare Advantage, Supplement, and Part D plans. The agency explains how different policies coordinate with Original Medicare and local provider networks. Clients receive personalized attention to understand enrollment windows and avoid late penalties. An initial assessment begins with a complimentary review of current coverage and prescription needs before any plan recommendations are made.

NI
13640 W Colonial Dr ste 150
NL Insurance Solutions Inc
Medicare Insurance Agent · Winter Garden, FL

NL Insurance Solutions Inc offers comprehensive guidance on Medicare insurance options for residents in and around Winter Garden, FL. The agency specializes in helping clients navigate Original Medicare, Medicare Advantage, and Medicare Supplement plans. By assessing individual healthcare needs and budgets, they assist in comparing coverage choices during enrollment periods. Their service extends to commercial sectors, including local offices, warehouses, and food service businesses needing employee or owner health coverage.

FM
15000 Stratus Lp
Fabio Motta - Life and Health Insurance
Medicare Insurance Agent · Winter Garden, FL

Located in Winter Garden, FL, Fabio Motta - Life and Health Insurance assists local residents with selecting Medicare insurance plans for their healthcare needs. Commercial coverage options are also available to area businesses. Serving seniors and individuals throughout Winter Garden and the surrounding Central Florida region, the agency helps clients compare plan benefits during enrollment periods. After initial enrollment, the office provides follow-up assistance and coverage reviews between regular visits to address changing medical requirements or plan adjustments.

CF
213 S Dillard St
Central Florida Insurance Advisors
Medicare Insurance Agent · Winter Garden, FL

Central Florida Insurance Advisors, based in Winter Garden, FL, is known for guiding Medicare beneficiaries through the complexities of original Medicare, Medicare Advantage, and Part D prescription drug plans. The agency focuses on helping individuals assess their healthcare needs and budget during the annual enrollment period. It provides personalized, local assistance to retirees and younger disability recipients. A specialty service it can offer is complete assistance with Medicare Supplement plan comparisons to fill coverage gaps.

HI
1165 E Plant St #6
Hillcrest Insurance Agency
Medicare Insurance Agent · Winter Garden, FL
(407) 656-2211
hillcrestinsurance.com
AI
502 S Woodland St
Abney Insurance Agency
Medicare Insurance Agent · Winter Garden, FL
(407) 877-6110
abneyagency.com
AS
1025 Bj Brandy Cove
Angel Shield Insurance
Medicare Insurance Agent · Winter Garden, FL
(689) 236-4979
angelshieldinsurance.com
SI
Raintree Building, 310 S Dillard St STE 150
Sunline Insurance Agency
Medicare Insurance Agent · Winter Garden, FL
(407) 933-7866
sunlineinsagency.com
PS
13640 W Colonial Dr #120
Pideme Seguro Insurance
Medicare Insurance Agent · Winter Garden, FL
(321) 521-1449
web.apizeal.com/LuisMarruffo
SI
5736 Hamlin Groves Tr #162
Sheldon Insurance
Medicare Insurance Agent · Winter Garden, FL
(407) 792-0686
sheldonpalmesinsurance.com
BI
1218 Winter Garden Vineland Rd #128
Budget Insurance Offices, Inc. - Winter Garden
Medicare Insurance Agent · Winter Garden, FL
(407) 877-0878
budgetinsurancewintergarden.com
BI
1201 Winter Garden Vineland Rd #4B
Bacci Insurance
Medicare Insurance Agent · Winter Garden, FL
(321) 946-8297
baccinsure.com
BI
Charlotte St
Blu IQ LLC
Medicare Insurance Agent · Winter Garden, FL
(561) 876-6400
bluiqinsurance.com

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

Medicare insurance agents in Florida do not charge you a fee for their services. Their compensation comes from the insurance companies whose plans you select. Plan costs vary widely: Medicare Advantage plans may have $0 monthly premiums, while Medigap plans in Florida can range from $100 to $300 per month depending on your age and health. Part D drug plan premiums average around $30 to $60 per month. This is general information and not insurance advice.

About medicare insurance agents in Winter Garden

A Medicare insurance agent in Winter Garden, Florida can help you compare Medicare Advantage, Medigap, and Part D plans. Florida law requires agents to be licensed and to follow specific marketing guidelines, including a 12-month lock-in period for Medicare Advantage plans. Local agents understand the network of hospitals and doctors in Orange County, making it easier to choose a plan that fits your needs.

Frequently Asked Questions

What does a Medicare insurance agent in Winter Garden do?

A Medicare insurance agent helps you review and enroll in Medicare plans, such as Part D drug plans or Medicare Advantage. They explain coverage options, costs, and provider networks. Agents do not charge you directly; they are paid by insurance companies.

When can I enroll in Medicare in Winter Garden, Florida?

You can enroll during your Initial Enrollment Period, which starts three months before you turn 65 and ends three months after. Florida also has an Annual Enrollment Period from October 15 to December 7 each year. Special Enrollment Periods are available for certain life events.

Do Medicare agents in Florida have to follow special rules?

Yes. Florida law requires agents to complete annual training and follow strict marketing rules. For example, agents cannot make unsolicited phone calls or door-to-door sales for Medicare plans. They must also explain plan changes clearly each year.

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.