The top-rated medicare insurance agent in Westport, Connecticut is The NEST Agency, rated 5.0 stars across 269 reviews. Other highly rated options include Jeff Boley, Independent Insurance Agent, HealthMarkets Insurance Agency, Cross Private Client Insurance, Smith Brothers Insurance. This directory lists 16 medicare insurance agents serving Westport.
Comparison
| # | Name | Address | Phone |
|---|---|---|---|
| 1 | The NEST Agency | 163 Main St | (203) 428-4338 |
| 2 | Jeff Boley, Independent Insurance Agent, HealthMarkets Insurance Agency | 69 Kings Hwy N | (203) 247-3312 |
| 3 | Cross Private Client Insurance | 1 Turkey Hill Rd S | (203) 655-6974 |
| 4 | Smith Brothers Insurance | 1720 Post Rd E Suite 222 | (203) 655-9766 |
| 5 | Dalila Namy - State Farm Insurance Agent | 793 Post Rd E Ste A101 | (203) 429-0031 |
| 6 | Howard & Gay Insurance | 979 Post Rd E | (203) 340-9540 |
| 7 | Medicare Benefits Hotline | 154 Main St | (203) 590-7546 |
| 8 | Dominick Valente: Allstate Insurance | 8 Church St S | (203) 226-1182 |
| 9 | Promax Insurance Agency | 300 Post Rd E | (475) 275-1238 |
| 10 | AssuredPartners Northeast formally Sachs Walsh Ins | 728 Post Rd E | (203) 227-7787 |
Nestled in Westport, CT, The NEST Agency serves clients throughout Fairfield County and the surrounding region as a dedicated Medicare insurance agent. It provides guidance on Original Medicare, helping individuals navigate both Parts A and B coverage options. The agency also supports enrollment in Medicare Supplement plans designed to fill gaps in traditional Medicare, and it assists with Medicare Advantage plans in the local area. Its specific services include coordinating prescription drug coverage under Part D and helping clients understand their annual enrollment choices.
Jeff Boley, Independent Insurance Agent, HealthMarkets Insurance Agency in Westport, CT, provides a full range of Medicare insurance solutions, including plans for medical and prescription drug coverage. He assists clients during enrollment periods and ongoing plan changes. Service plans also include annual policy reviews and support for benefit adjustments as healthcare needs evolve. He works with individuals to identify suitable options from available carriers and maintains contact for questions regarding claims or coverage. The agency services single-family homes, apartments, retail, and restaurants.
Homeowners and other residents of Westport, Connecticut seeking guidance on their healthcare options work with Cross Private Client Insurance. As a local medicare insurance agent, this company assists clients in understanding their Medicare plan choices and enrollment periods. The team provides straightforward, personal consultations to help match individuals with suitable coverage based on their specific needs. Their service area also extends to clients living in nearby Fairfield, ensuring broader access for the community.
Smith Brothers Insurance serves Westport, Connecticut, and the surrounding communities in Fairfield County. The company focuses exclusively on Medicare insurance, handling Medicare Advantage plans, Medicare Supplement policies, and Part D prescription drug coverage for eligible individuals. This local agency helps clients navigate enrollment periods, plan changes, and coverage options to match their healthcare needs and budgets. For a typical client, the company uses a straightforward, educational approach, reviewing available plans side by side and explaining the differences in costs and benefits before making a recommendation.
Clients seeking Medicare guidance from Dalila Namy - State Farm Insurance Agent in Westport, CT can choose between a one-time consultation to review initial plan options or recurring annual check-ins to accommodate changing health needs. Coverage assistance typically focuses on comparing Original Medicare, Medicare Advantage, and Part D prescription drug plans available locally. As a licensed Medicare insurance agent, representatives help clarify enrollment periods and plan details specific to Fairfield County residents. This service is available on an as-needed basis for those requiring immediate plan adjustments outside of standard enrollment windows.
Howard & Gay Insurance specializes in Medicare insurance guidance and plan selection in Westport, CT, then assists clients with enrolling and managing their coverage through ongoing support. It works with individuals navigating their initial Medicare eligibility as well as those reviewing their current plans during the annual open enrollment period. This agency also helps address concerns about coverage gaps or rising out-of-pocket costs that may arise after a change in health status.
As open enrollment season approaches each fall, Medicare Benefits Hotline in Westport, CT helps local seniors sort through plan options without pressure. The agency focuses on connecting clients to the right Medicare Advantage or supplement coverage based on individual health needs. Each agent reviews a person’s current medications and preferred providers before recommending specific plans for the upcoming year. The process generally begins with a brief, in-person inspection of existing coverage documents and a discussion of any health changes.
Dominick Valente: Allstate Insurance assists individuals in Westport, CT with navigating Medicare coverage options. The agency specializes in explaining Medicare supplement plans and Part D prescription drug plans to help clients manage healthcare costs. Seniors and those approaching eligibility receive clear guidance on enrollment periods and plan benefits. The agency also advises on how Medicare coordinates with group health plans. Commercial sectors served include nearby professional offices, medical clinics, warehouses, and food service businesses.
Promax Insurance Agency serves residents of Westport, Connecticut, helping them navigate their individual Medicare plan options for medical and prescription drug coverage. The agency also advises on Medicare supplements and Advantage plans for commercial clients within the surrounding area. Assistance includes initial enrollment, plan comparisons, and annual review of coverage changes. The agent maintains ongoing contact with each client, providing follow-up support between regular plan check-ins to address any new questions or adjustments to health needs.
AssuredPartners Northeast, formally Sachs Walsh Ins, is a Medicare insurance agent based in Westport, CT, known for guiding clients through plan options. The agency helps individuals evaluate Medicare Advantage, Supplement, and Part D drug coverage to match their healthcare needs and budgets. It serves local retirees and those approaching eligibility with personalized consultations. A specialty service it can add on is enrollment support for dual-eligible beneficiaries who qualify for both Medicare and Medicaid.
What Does a a Medicare Insurance Agent in Westport Cost?
Medicare insurance agents in Connecticut do not charge you for their services. Their compensation comes from the insurance companies whose plans they sell. Typical Medicare Part B premiums in 2025 are about $185 per month for most people but can be higher based on income. Medicare Advantage plans often have low or zero monthly premiums but may have copays and deductibles. Part D drug plan premiums vary widely from around $10 to $100 per month depending on the plan and your medications. This is general information not insurance advice.
About medicare insurance agents in Westport
Medicare insurance agents in Westport Connecticut help residents compare plans and enroll in Medicare Part A Part B Part D and Medicare Advantage. Connecticut law requires agents to be licensed by the state and follow strict marketing guidelines. Local agents understand the specific plan options available in Fairfield County and can explain how Connecticut Medicare Savings Programs work.
Frequently Asked Questions
What does a Medicare insurance agent in Westport do?
A Medicare insurance agent in Westport helps you review your health needs compare Medicare plans and enroll in the right coverage. They can explain the differences between Original Medicare Medicare Advantage and Part D drug plans. Agents do not charge you directly they are paid by the insurance companies.
When can I enroll in Medicare in Connecticut?
Your initial enrollment period starts three months before you turn 65 and ends three months after your birthday month. Connecticut also has a Medicare Savings Program that may help with premiums and cost sharing. Missing your initial enrollment can lead to late penalties so it is best to start the process early.
Are Medicare insurance agents in Westport licensed differently in Connecticut?
Yes all Medicare insurance agents in Connecticut must hold a valid insurance producer license from the Connecticut Insurance Department. They must also complete annual Medicare training and follow federal marketing rules. This ensures they provide accurate information about plan options and costs.
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