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Compare Medicare Insurance Agents in Winter Haven, FL
Compare medicare insurance agents in Winter Haven. Review contact information and insurance categorys before you decide.
18 agents listed
Updated May 2026
Winter Haven, FL
Important: Listings are compiled from publicly available sources and have not been independently verified by BeforeInsuranceUSA.com. We do not endorse any agent or guarantee outcomes. Verify licensing and disciplinary status with the Department of Insurance of Florida before hiring.
Showing 18 medicare insurance agents in Winter Haven, FL
Listings are displayed in no particular order and are not ranked by BeforeInsuranceUSA. Order does not constitute a recommendation or endorsement of any agent.
Rob Semans - State Farm Insurance Agent
639 1st St S, Winter Haven, FL 33880
(863) 299-1274
robsemans.com
Team Barfield - Barfield Insurance
141 5th St NW #302, Winter Haven, FL 33881
(863) 662-3134
teambarfield.com
Barfield Insurance & Financial Services Inc.
110 Spirit Lake Rd Unit 5, Winter Haven, FL 33880
(863) 293-5400
insurewithbarfield.com
Karen Bryan - State Farm Insurance Agent
391 Ave A SW, Winter Haven, FL 33880
(863) 268-2800
choosekaren.com
Total Care Consultants Llc
1503 Havendale Blvd NW, Winter Haven, FL 33881
(863) 268-2972
tccflorida.com
GreatFlorida Insurance: Brock Schnabel
5658 Cypress Gardens Blvd, Winter Haven, FL 33884
(863) 594-2600
winterhaven.greatflorida.com
AmeriLife of Polk County, LLC
6322 Cypress Gardens Blvd, Winter Haven, FL 33884
(863) 291-4111
amerilife.com
Garland Insurance fka Victory Insurance
116 W Central Ave, Winter Haven, FL 33880
(863) 683-9334
Clearvue Insurance Agency (Formerly Lorna Wilson Agency)
Please call for an appointment, 2422 Wildwood Ct, Winter Haven, FL 33884
(863) 521-7605
planenroll.com
Dershimer Insurance Agency
190 Avenue A NW, Winter Haven, FL 33881
(863) 299-8330
dershimerinsurance.com
Carroll-Marshall Insurance, Inc.
205 Ave G SW, Winter Haven, FL 33880
(863) 293-1111
cminsure.com
Swift Insurance Agency FL
400 Ave C NE, Winter Haven, FL 33881
(863) 546-8440
Health Insurance For You
2014 Wentworth Pl, Winter Haven, FL 33881
(407) 614-1725
healthinsforyou.com
HealthMarkets Insurance - Vernon Douglas
100 Homewood Dr, Winter Haven, FL 33880
(863) 412-1947
healthmarkets.com
Medicare insurance agents in Winter Haven Florida help residents compare plans and enroll during open enrollment periods. Florida law requires agents to be licensed by the state and follow specific marketing guidelines. Local agents understand the needs of Polk County seniors and can explain Medigap Advantage and Part D options.
What Does a Medicare Insurance Agent in Winter Haven Cost?
Medicare insurance agent services in Florida are generally free to you because agents receive commissions from insurance carriers. Plan costs vary widely: Medicare Advantage plans may have $0 monthly premiums while Medigap plans can cost $100 to $300 per month depending on your age and location. Part D prescription drug plans average $30 to $80 per month in Florida. This is general information not insurance advice. Consult a licensed agent for your specific situation.
* Cost estimates are general ranges based on publicly available data and compiled using automated research tools. Actual fees vary by agent and case complexity. This is not insurance advice — consult directly with an agent for fee specifics.
Frequently Asked Questions
What does a Medicare insurance agent in Winter Haven do?
A licensed agent helps you compare Medicare plans like Part D and Medicare Advantage. They explain coverage options and assist with enrollment. Agents must follow Florida insurance regulations and cannot charge you for their advice.
When can I enroll in Medicare in Winter Haven Florida?
Initial enrollment starts three months before you turn 65 and lasts seven months. The Annual Enrollment Period runs from October 15 to December 7 each year. Florida also has a Special Enrollment Period for certain life changes like moving or losing other coverage.
Are Medicare insurance agents free in Florida?
Yes agents are typically paid by insurance companies not by you. Their commissions are built into the plan premiums. You pay the same premium whether you use an agent or not. Always confirm with the agent that their services are no cost to you.
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BeforeInsuranceUSA.com is not an insurance agency, agent referral service, or insurance advice provider. No agent-client relationship is formed by submitting a form or using this site. We do not endorse, recommend, or vouch for the qualifications of any agent. Past results do not guarantee future outcomes. Each situation is different. Verify agent credentials with your state department of insurance before hiring.
About Our Listings
Agents listed on BeforeInsuranceUSA.com are compiled from publicly available directories, state department of insurance records, and business listings. Inclusion does not constitute endorsement. We do not verify agent licensing, disciplinary status, or qualifications. Verify each agent's current standing with the Department of Insurance of Florida.