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Compare Supplemental Insurance Agents in Winter Haven, FL

Looking for a supplemental insurance agent in Winter Haven? Review the directory below to compare your options.

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 supplemental 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
Acceptance Insurance
910 Havendale Blvd NW #134, Winter Haven, FL 33881
(863) 733-7006 locations.acceptance.com
Freeway Insurance
1136 6th St NW, Winter Haven, FL 33881
(863) 733-7003 locations.freeway.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
American Insurance Inc
3610 Havendale Blvd, Winter Haven, FL 33881
(863) 965-2886 americaninsuranceinc.com
AmeriLife of Polk County, LLC
6322 Cypress Gardens Blvd, Winter Haven, FL 33884
(863) 291-4111 amerilife.com
White Chip Insurance – Winter Haven
1217 6th St SW, Winter Haven, FL 33880
(863) 342-6723 whitechipinsurance.com
Lacy McClintock - State Farm Insurance Agent
600 3rd St SW, Winter Haven, FL 33880
(863) 294-3580 teamlacy.com
Garland Insurance fka Victory Insurance
116 W Central Ave, Winter Haven, FL 33880
(863) 683-9334
Cypress Insurance Management
3021 Cypress Gardens Rd, Winter Haven, FL 33884
(863) 326-1885 cypressinsuranceonline.com
Sealy Insurance
3395 Cypress Gardens Rd, Winter Haven, FL 33884
(863) 324-3100
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
HealthMarkets Insurance - Vernon Douglas
100 Homewood Dr, Winter Haven, FL 33880
(863) 412-1947 healthmarkets.com

Supplemental insurance agents in Winter Haven Florida help residents find plans that cover gaps in Medicare or employer health coverage. Florida law requires agents to be licensed by the state and to follow strict disclosure rules. Many Winter Haven agents specialize in plans for retirees and seasonal residents.

What Does a Supplemental Insurance Agent in Winter Haven Cost?

Supplemental insurance costs in Florida vary by plan type age and health status. Medigap plans in Winter Haven typically range from 100 to 300 dollars per month for a 65 year old. Medicare Advantage plans often have low or zero monthly premiums but include copays and deductibles. This is general information not insurance advice.

* 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 is a supplemental insurance agent in Winter Haven?
A supplemental insurance agent is a licensed professional who helps you buy Medigap Medicare Advantage or other private health plans. They can explain how Florida insurance laws affect your coverage options. Agents in Winter Haven often work with local carriers like Florida Blue or Humana.
Do I need a separate agent for supplemental insurance in Florida?
You can buy supplemental insurance directly from a company but an agent can compare multiple plans for you. Florida allows agents to charge fees or earn commissions from insurers. Using an agent does not usually cost you extra.
What Florida laws apply to supplemental insurance agents?
Florida Statute 626.112 requires all insurance agents to hold a valid license. Agents must also follow the Florida Insurance Code which includes rules on advertising and disclosure. For Medicare supplements Florida has a six-month open enrollment window when you first turn 65.