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Find Medicare Insurance Agents Near You in Estero, FL

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

The top-rated medicare insurance agent in Estero, Florida is Regency Insurance Group a Hilb Group Company, rated 4.8 stars across 1,371 reviews. Other highly rated options include Ted Todd Insurance: Allstate Insurance, Rich Mathews - State Farm Insurance Agent, Brightway Insurance, The Dorrian Agency. This directory lists 11 medicare insurance agents serving Estero.

Showing 11 medicare insurance agents in Estero, FLListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Regency Insurance Group a Hilb Group Company23190 Fashion Dr p216(239) 628-4344
2Ted Todd Insurance: Allstate Insurance23160 Fashion Dr Ste 223(239) 561-1100
3Rich Mathews - State Farm Insurance Agent9510 Corkscrew Palms Cir #4(239) 992-8896
4Brightway Insurance, The Dorrian Agency19970 S Tamiami Trl #104(239) 280-5480
5Lane Insurance GroupLocated in the Galleria, 21105 Design Parc Ln #103(239) 947-7474
6Charley Insurance23160 Fashion Dr #226(239) 280-5555
7Sagacity Insurance Professionals10600 Chevrolet Way Suite 224(239) 533-9755
8State Insurance USA, LLC10600 Chevrolet Way #107(239) 567-9992
9Florida Blue Center - Ft. Myers8041 Plaza del Lago Dr(239) 494-3460
10Coastline Insurance Group, Inc.23190 Fashion Dr #210(239) 217-6005
RI
23190 Fashion Dr p216
Regency Insurance Group a Hilb Group Company
Medicare Insurance Agent · Estero, FL

Regency Insurance Group, a Hilb Group company, serves clients in Estero, Florida, and the surrounding Lee County area. As a Medicare insurance agent, it helps individuals navigate their coverage options during annual enrollment and special enrollment periods. The company assists with comparing Medicare Advantage and Medicare Supplement plans to match different healthcare needs. It also handles prescription drug plan enrollments and provides guidance on plan transitions.

TT
23160 Fashion Dr Ste 223
Ted Todd Insurance: Allstate Insurance
Medicare Insurance Agent · Estero, FL

Ted Todd Insurance: Allstate Insurance serves individual homeowners and retired residents in Estero, Florida, offering Medicare insurance agent services that help clients navigate plan options and enroll in suitable coverage. The agency assists with evaluating Part D drug plans, Medicare Advantage selections, and supplemental policies to match healthcare needs. Conveniently located to support the local community, the office also extends its Medicare guidance to neighboring Bonita Springs within the greater metropolitan area.

RM
9510 Corkscrew Palms Cir #4
Rich Mathews - State Farm Insurance Agent
Medicare Insurance Agent · Estero, FL

Rich Mathews - State Farm Insurance Agent provides Medicare insurance guidance in Estero, Florida, helping clients understand their coverage options for medical and prescription needs. The agency offers annual plan reviews and enrollment support to ensure beneficiaries maintain appropriate protection as their healthcare requirements change. Ongoing consultation helps policyholders navigate plan updates and deadlines throughout the year. The firm serves individual homeowners, residents of condominium and apartment complexes, retail employees, and workers in the local restaurant industry within the surrounding region.

BI
19970 S Tamiami Trl #104
Brightway Insurance, The Dorrian Agency
Medicare Insurance Agent · Estero, FL

Brightway Insurance, The Dorrian Agency serves Estero, Florida, and the surrounding communities in Southwest Florida. It handles Medicare insurance plans, including Medicare Supplement, Medicare Advantage, and Part D prescription drug coverage. With a local office, it guides clients through the annual enrollment period and plan options. The agency uses a thorough needs assessment to evaluate each person’s healthcare usage and budget before matching them with a suitable carrier.

LI
Located in the Galleria, 21105 Design Parc Ln #103
Lane Insurance Group
Medicare Insurance Agent · Estero, FL

Lane Insurance Group in Estero, FL distinguishes between initial enrollment assistance for Medicare and ongoing annual plan reviews, focusing on Part D prescription drug coverage and Medicare Advantage options. As a local medicare insurance agent, the agency can discuss coverage changes during the annual enrollment period. Services are available on an as-needed basis, allowing clients to request appointments for plan comparisons or questions outside of scheduled renewal seasons.

CI
23160 Fashion Dr #226
Charley Insurance
Medicare Insurance Agent · Estero, FL

Charley Insurance specializes in Medicare supplement plans, Part D prescription drug coverage, and Medicare Advantage options for residents of Estero, Florida. It guides clients through annual enrollment periods, ensuring beneficiaries understand plan changes and network requirements. The agency also explains the differences between Original Medicare and private plans, helping individuals match coverage to their healthcare needs. During the fall open enrollment season, it assists seniors with reviewing and updating their policies to avoid gaps in prescription drug or hospital coverage.

SI
10600 Chevrolet Way Suite 224
Sagacity Insurance Professionals
Medicare Insurance Agent · Estero, FL

Sagacity Insurance Professionals helps individuals and families in Estero find suitable coverage for their healthcare needs. The agency specializes in Medicare insurance agent services, focusing on plans that meet specific medical and financial requirements. Clients receive assistance navigating enrollment periods and comparing policy options. The team works closely with local businesses across several commercial sectors, including professional offices, light manufacturing warehouses, and full-service food establishments in the surrounding area.

SI
10600 Chevrolet Way #107
State Insurance USA, LLC
Medicare Insurance Agent · Estero, FL

Serving residents of Estero and the surrounding area, State Insurance USA, LLC provides guidance on Medicare insurance options for individuals. Commercial coverage solutions are also available to meet the needs of local businesses and groups. The agency specializes in helping clients understand their plan choices during enrollment periods and annual review windows. Clear explanations are given so customers can make informed decisions about their healthcare coverage. Representatives assist with plan changes and new enrollments, ensuring a smooth process. The office is available for follow-up support and repeat service between regular visits.

FB
8041 Plaza del Lago Dr
Florida Blue Center - Ft. Myers
Medicare Insurance Agent · Estero, FL

As Florida’s open enrollment window approaches each fall, many retirees in Estero begin reviewing their prescription and supplemental coverage options. The Florida Blue Center in Ft. Myers provides local, guided assistance for Medicare insurance agent services tailored to individual health needs and budgets. Advisors review each client’s current plan, compare available Part D and Medicare Advantage alternatives, and explain how coverage works with area providers and pharmacies. A free initial assessment is offered to help determine the best fit for the coming year.

CI
23190 Fashion Dr #210
Coastline Insurance Group, Inc.
Medicare Insurance Agent · Estero, FL

Coastline Insurance Group, Inc. in Estero, FL, is known for helping residents navigate the complex Medicare system. The agency offers plans for Medicare Advantage, prescription drug coverage, and Medicare Supplement policies. These options are designed to cover a range of healthcare needs for senior clients. Agents take time to compare existing coverage with available plans. They explain plan structures annually during the enrollment window. A specialty service the agency can provide is assisting clients with understanding out-of-pocket costs and co-pay structures under each potential plan option.

PI
23160 Fashion Dr #217
Parlin Insurance Agency
Medicare Insurance Agent · Estero, FL
(239) 263-3141
parlininsurance.com

What Does a a Medicare Insurance Agent in Estero Cost?

Medicare insurance agents in Florida typically do not charge you directly for their services. They are paid commissions by insurance companies, so your cost is the same whether you use an agent or go directly to the carrier. Medicare Part B premiums in 2025 are generally around $174.70 per month for most beneficiaries, though higher income earners pay more. Medicare Advantage plans often have $0 monthly premiums but may have copays and deductibles. This is general information, not insurance advice.

About medicare insurance agents in Estero

Medicare insurance agents in Estero, Florida help residents navigate Original Medicare, Medicare Advantage, and Part D drug plans. Florida law requires agents to be licensed by the state and follow strict marketing guidelines under Florida Statute 626.88. These agents provide free assistance with plan comparisons and annual enrollment periods, ensuring you find coverage that fits your health needs and budget.

Frequently Asked Questions

What does a Medicare insurance agent in Estero do?

A Medicare insurance agent helps you compare plans, enroll in Medicare Part A and Part B, and choose Medicare Advantage or Medigap policies. They are licensed in Florida and must follow state rules on marketing and disclosure.

Is there a time limit to sign up for Medicare in Florida?

Yes. Your Initial Enrollment Period starts three months before you turn 65 and ends three months after. Florida also has a General Enrollment Period from January 1 to March 31 each year if you miss your initial window. Late enrollment can result in permanent penalties.

Can a Medicare agent help me with Medicare Advantage plans in Estero?

Yes. Agents can show you all Medicare Advantage plans available in Lee County, including HMO and PPO options. They must explain plan networks, costs, and coverage limits as required by Florida law.

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.