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HomeMedicare Insurance AgentsFlorida › Winter Haven

Find Medicare Insurance Agents Near You in Winter Haven, FL

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

The top-rated medicare insurance agent in Winter Haven, Florida is Rob Semans - State Farm Insurance Agent, rated 4.9 stars across 982 reviews. Other highly rated options include Team Barfield - Barfield Insurance, Barfield Insurance & Financial Services Inc., Karen Bryan - State Farm Insurance Agent. This directory lists 18 medicare insurance agents serving Winter Haven.

Showing 18 medicare insurance agents in Winter Haven, FLListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Rob Semans - State Farm Insurance Agent639 1st St S(863) 299-1274
2Team Barfield - Barfield Insurance141 5th St NW #302(863) 662-3134
3Barfield Insurance & Financial Services Inc.110 Spirit Lake Rd Unit 5(863) 293-5400
4Karen Bryan - State Farm Insurance Agent391 Ave A SW(863) 268-2800
5Total Care Consultants Llc1503 Havendale Blvd NW(863) 268-2972
6GreatFlorida Insurance: Brock Schnabel5658 Cypress Gardens Blvd(863) 594-2600
7AmeriLife of Polk County, LLC6322 Cypress Gardens Blvd(863) 291-4111
8Clearvue Insurance Agency (Formerly Lorna Wilson Agency)308 Ave G SW Suite 201(863) 866-8990
9Garland Insurance fka Victory Insurance116 W Central Ave(863) 683-9334
10Cypress Insurance Management3021 Cypress Gardens Rd(863) 326-1885
RS
639 1st St S
Rob Semans - State Farm Insurance Agent
Medicare Insurance Agent · Winter Haven, FL

Rob Semans - State Farm Insurance Agent serves the Winter Haven, Florida area, specializing in Medicare insurance guidance for local seniors and residents approaching retirement. This agency helps clients navigate Medicare plans, including Medicare Advantage and Medicare Supplement insurance options. Their licensed team assists with understanding enrollment periods and comparing plan benefits. For individuals in Winter Haven seeking Medicare coverage, the office provides plan selection and annual enrollment support. They also handle Part D prescription drug plan evaluations and sign-ups.

TB
141 5th St NW #302
Team Barfield - Barfield Insurance
Medicare Insurance Agent · Winter Haven, FL

Team Barfield - Barfield Insurance offers guidance on Medicare supplement plans, Medicare Advantage options, and prescription drug coverage in Winter Haven, Florida. The agency helps clients review annual plan changes and enroll during designated periods. It provides ongoing support for policy questions and claim assistance throughout the year. Services cover individual single-family homes, apartments, retail businesses, and local restaurants.

BI
110 Spirit Lake Rd Unit 5
Barfield Insurance & Financial Services Inc.
Medicare Insurance Agent · Winter Haven, FL

Homeowners and retirees in Winter Haven, Florida, turn to Barfield Insurance & Financial Services Inc. for Medicare insurance agent support, helping them navigate plan options like supplements, advantage plans, and Part D coverage. The company works with individuals to review their healthcare needs and compare available policies. Its services extend to residents of nearby Lakeland, ensuring greater access for those in the broader Polk County metro area.

KB
391 Ave A SW
Karen Bryan - State Farm Insurance Agent
Medicare Insurance Agent · Winter Haven, FL

Serving Winter Haven and the surrounding communities of Central Florida, Karen Bryan as a State Farm Insurance Agent handles Medicare insurance needs for eligible individuals. The agency focuses on helping clients understand their plan options, including coverage gaps and prescription drug choices. Each client consultation begins with a thorough review of their current health needs and budget. The agency typically works through a step-by-step process, comparing available plans to find suitable coverage before assisting with enrollment paperwork.

TC
1503 Havendale Blvd NW
Total Care Consultants Llc
Medicare Insurance Agent · Winter Haven, FL

Unlike one-time Medicare enrollment assistance, Total Care Consultants Llc in Winter Haven, FL offers ongoing support for plan changes and annual reviews. They help clients compare Medicare insurance options to find coverage that fits their healthcare needs and budget. Guidance includes understanding plan details, prescription drug coverage, and supplemental policies. Their service is available on both a scheduled and as-needed basis, allowing clients to arrange appointments for specific questions or regular check-ins throughout the year.

GI
5658 Cypress Gardens Blvd
GreatFlorida Insurance: Brock Schnabel
Medicare Insurance Agent · Winter Haven, FL

GreatFlorida Insurance Brock Schnabel offers Medicare Advantage and prescription drug plan guidance to Winter Haven residents. The agency assists individuals with comparing coverage options and understanding enrollment forms. Specialists explain how original Medicare works alongside supplemental policies to manage out-of-pocket costs. Seasonal support includes navigating the Annual Enrollment Period each fall, ensuring clients review changes in benefits or provider networks before December 7th deadline.

AP
6322 Cypress Gardens Blvd
AmeriLife of Polk County, LLC
Medicare Insurance Agent · Winter Haven, FL

With Medicare’s annual enrollment period approaching, many Winter Haven seniors face complex plan choices between Original Medicare, Advantage, and Part D drug coverage. AmeriLife of Polk County, LLC helps local beneficiaries navigate these options with clear explanations of costs, networks, and out-of-pocket limits. A licensed agent will meet clients in person to review their current health needs and prescriptions before comparing their coverage against available local plans. Initial assessment begins with a no-prep, complimentary review of each client’s medical expenses and provider preferences to determine eligibility.

CI
308 Ave G SW Suite 201
Clearvue Insurance Agency (Formerly Lorna Wilson Agency)
Medicare Insurance Agent · Winter Haven, FL

Serving residents of Winter Haven, Clearvue Insurance Agency, formerly Lorna Wilson Agency, helps individuals navigate their Medicare insurance options. The agency also assists clients with related supplemental coverage needs throughout the local area. By reviewing each client’s healthcare requirements and budget, the agent works to match them with suitable plans from available providers. After enrollment, the office follows up to address any questions and remains available for plan adjustments during the annual enrollment period, ensuring ongoing support between regular health visits.

GI
116 W Central Ave
Garland Insurance fka Victory Insurance
Medicare Insurance Agent · Winter Haven, FL

Garland Insurance, formerly known as Victory Insurance, provides Medicare insurance guidance to clients in Winter Haven, Florida. The agency focuses on helping individuals understand their coverage options and navigate plan selections for their healthcare needs. Specialty add-ons include assistance with Medicare Supplement and Part D prescription drug plans. The agency can serve commercial accounts such as small offices, distribution warehouses, and food service establishments requiring group health insurance solutions.

CI
3021 Cypress Gardens Rd
Cypress Insurance Management
Medicare Insurance Agent · Winter Haven, FL

Cypress Insurance Management in Winter Haven, Florida, is known for guiding individuals through the complexities of Medicare plan selection. The agency helps clients evaluate their coverage options, including Medicare Advantage and Supplement plans. Its service range also includes assisting with Part D prescription drug plans to ensure proper medication coverage. As a local Medicare insurance agent, it provides personalized consultations to address specific healthcare needs. For add-on coverage, it can assist with enrolling in Medicare plan options that include routine vision and dental benefits for more comprehensive care.

JL
1750 Havendale Blvd NW STE 1
J&KC Life Insurance Agency
Medicare Insurance Agent · Winter Haven, FL
(863) 368-5964
facebook.com/jkclifeinsurance
SI
3395 Cypress Gardens Rd
Sealy Insurance
Medicare Insurance Agent · Winter Haven, FL
(863) 324-3100
WI
Please call for an appointment, 2422 Wildwood Ct
Whigham Insurance
Medicare Insurance Agent · Winter Haven, FL
(863) 521-7605
planenroll.com
SI
400 Ave C NE
Swift Insurance Agency FL
Medicare Insurance Agent · Winter Haven, FL
(863) 546-8440
CM
205 Ave G SW
Carroll-Marshall Insurance, Inc.
Medicare Insurance Agent · Winter Haven, FL
(863) 293-1111
cminsure.com
DI
190 Avenue A NW
Dershimer Insurance Agency
Medicare Insurance Agent · Winter Haven, FL
(863) 299-8330
dershimerinsurance.com
HI
2014 Wentworth Pl
Health Insurance For You
Medicare Insurance Agent · Winter Haven, FL
(407) 614-1725
healthinsforyou.com
HI
100 Homewood Dr
HealthMarkets Insurance - Vernon Douglas
Medicare Insurance Agent · Winter Haven, FL
(863) 412-1947
healthmarkets.com/local-health-insurance-agent/vdouglas

What Does a 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.

About medicare insurance agents in Winter Haven

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.

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.

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.