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Find Supplemental Insurance Agents Near You in Westport, CT

Browse supplemental insurance agents serving Westport, Connecticut. Updated 2026-07-14.

The top-rated supplemental 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 14 supplemental insurance agents serving Westport.

Showing 14 supplemental insurance agents in Westport, CTListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1The NEST Agency163 Main St(203) 428-4338
2Jeff Boley, Independent Insurance Agent, HealthMarkets Insurance Agency69 Kings Hwy N(203) 247-3312
3Cross Private Client Insurance1 Turkey Hill Rd S(203) 655-6974
4Smith Brothers Insurance1720 Post Rd E Suite 222(203) 655-9766
5Dalila Namy - State Farm Insurance Agent793 Post Rd E Ste A101(203) 429-0031
6Howard & Gay Insurance979 Post Rd E(203) 340-9540
7Dominick Valente: Allstate Insurance8 Church St S(203) 226-1182
8Promax Insurance Agency300 Post Rd E(475) 275-1238
9AssuredPartners Northeast formally Sachs Walsh Ins728 Post Rd E(203) 227-7787
10fortify insurance group24 Punch Bowl Dr(203) 226-4077
NA
163 Main St
The NEST Agency
Supplemental Insurance Agent · Westport, CT

The NEST Agency, serving Westport and the surrounding Connecticut area, operates as a local supplemental insurance agent. It helps clients bridge gaps left by traditional major medical plans by offering policies that cover out-of-pocket costs. These supplemental plans can provide benefits for hospital confinement, accidental injuries, and critical illness diagnoses. The agency specifically handles cancer insurance policies to assist with treatment expenses, and it also offers policies for hospital indemnity benefits during inpatient stays.

JB
69 Kings Hwy N
Jeff Boley, Independent Insurance Agent, HealthMarkets Insurance Agency
Supplemental Insurance Agent · Westport, CT

Jeff Boley, Independent Insurance Agent with HealthMarkets Insurance Agency in Westport, CT, offers a range of supplemental insurance products to help cover costs not paid by primary health plans. Services include Medicare supplements, hospital indemnity, accident, and critical illness policies that provide direct cash benefits to policyholders. Clients receive year-round support for claims assistance and plan reviews to ensure their coverage remains appropriate. This agency serves the supplemental insurance needs of individuals, including those living in single-family homes, as well as owners of apartments, retail establishments, and local restaurants.

CP
1 Turkey Hill Rd S
Cross Private Client Insurance
Supplemental Insurance Agent · Westport, CT

Cross Private Client Insurance serves homeowners, businesses, and property managers in Westport, Connecticut, who need supplemental insurance coverage to fill gaps left by standard policies. The agency focuses on offering tailored solutions for unexpected expenses, such as deductibles or equipment breakdowns, ensuring clients maintain financial stability after a loss. Its services include policy review and plan customization to address unique local risks. Cross Private Client Insurance also extends coverage options to clients in neighboring Fairfield and the surrounding communities of southern Fairfield County.

SB
1720 Post Rd E Suite 222
Smith Brothers Insurance
Supplemental Insurance Agent · Westport, CT

As summer storms and unplanned injuries often disrupt household budgets across Fairfield County, Smith Brothers Insurance offers tailored supplemental policies to Westport residents. These plans help cover costs that standard medical insurance may leave behind, such as deductibles and out-of-pocket expenses. The company provides personal consultations to explain policy options and review existing coverage. An initial assessment is typically conducted to identify gaps and recommend suitable solutions.

DN
793 Post Rd E Ste A101
Dalila Namy - State Farm Insurance Agent
Supplemental Insurance Agent · Westport, CT

Dalila Namy - State Farm Insurance Agent serves Westport, Connecticut, and the surrounding communities. The agency handles supplemental insurance policies designed to fill gaps in primary health or life coverage. For typical clients, this often means assessing existing plans to recommend options like accident or hospital indemnity insurance. The general approach involves discussing specific coverage needs and available policy features. Each job is managed by reviewing individual circumstances and explaining plan details clearly, ensuring clients understand how supplemental benefits work alongside their core insurance.

HG
979 Post Rd E
Howard & Gay Insurance
Supplemental Insurance Agent · Westport, CT

Howard & Gay Insurance distinguishes between one-time policy reviews and ongoing plan adjustments for Westport residents. As a supplemental insurance agent, the company focuses on covering gaps left by primary health plans, such as copays or hospital stays. A typical consultation explains these coverage differences while outlining available policy riders or benefit limits. Service runs on a one-time, scheduled, or as-needed basis, depending on whether clients request an initial assessment or prefer periodic check-ins for plan changes.

DV
8 Church St S
Dominick Valente: Allstate Insurance
Supplemental Insurance Agent · Westport, CT

Dominick Valente: Allstate Insurance specializes in offering supplemental insurance solutions that bridge coverage gaps left by primary health plans. The agency provides personalized guidance, helping clients evaluate policies designed for unexpected medical costs and income disruptions. Located in Westport, CT, it serves local residents seeking to strengthen their financial safety net. As the winter months approach, it assists families in reviewing their policies to ensure adequate protection against seasonal illnesses and weather-related accidents not fully covered by standard insurance.

PI
300 Post Rd E
Promax Insurance Agency
Supplemental Insurance Agent · Westport, CT

As fall in Westport brings seasonal activities and the close of major enrollment periods, you may notice gaps in your medical coverage for routine care or unexpected incidents. Promax Insurance Agency responds by specializing as a supplemental insurance agent, helping you fill those coverage holes with affordable policies tailored to your budget and daily life. Their team explains how these plans work alongside your primary insurance, ensuring you understand potential savings before committing. The initial step involves a simple assessment of your current policy at their local office.

AN
728 Post Rd E
AssuredPartners Northeast formally Sachs Walsh Ins
Supplemental Insurance Agent · Westport, CT

AssuredPartners Northeast, formerly Sachs Walsh Ins, operates as a supplemental insurance agent in Westport, CT. The agency helps clients bridge gaps left by primary health plans, offering specialized add-ons such as accident, critical illness, and hospital indemnity coverage. These policies provide financial support for deductibles and out-of-pocket expenses. The company serves a range of commercial sectors, including corporate offices, warehouses, and food service establishments, tailoring its offerings to the unique risk exposures found in each business environment.

FI
24 Punch Bowl Dr
fortify insurance group
Supplemental Insurance Agent · Westport, CT

Fortify Insurance Group serves residents in the Westport, Connecticut, area by helping them select supplemental insurance policies that address gaps in primary coverage. The firm also assists local commercial clients seeking comparable protective plans for their businesses. Operating as a supplemental insurance agent, the company focuses on options that may provide financial support during illness, accident, or recovery. After an initial enrollment, the agent schedules periodic reviews to discuss potential changes in needs and follows up between regular visits to address any adjustments or questions that arise.

BQ
180 Post Rd E #204
Benson/Quinlan Insurance Agency, Inc
Supplemental Insurance Agent · Westport, CT
(203) 227-8448
bensonquinlan.com
EM
191 Post Rd W
Emerald Medicare - Fairfield, CT
Supplemental Insurance Agent · Westport, CT
(203) 403-6670
emeraldmedicare.com
SC
1720 Post Rd E
SterlingRisk of Connecticut
Supplemental Insurance Agent · Westport, CT
(203) 349-8472
sterlingrisk.com
CI
500 Post Rd E 2nd Floor
Consumers Insurance Inc.
Supplemental Insurance Agent · Westport, CT
(203) 349-8201
consumers-ins.com

What Does a a Supplemental Insurance Agent in Westport Cost?

Supplemental insurance agent services in Connecticut are typically commission-based meaning you pay no direct fee for their help. Medigap plan premiums in Westport range from about $100 to $300 per month depending on your age gender and plan choice. Costs vary by carrier and underwriting factors. This is general information and not insurance advice.

About supplemental insurance agents in Westport

Supplemental insurance agents in Westport Connecticut help residents fill gaps in Medicare coverage. Connecticut law requires Medigap plans to be guaranteed issue for eligible beneficiaries during open enrollment. Agents can explain local options like Plan G and Plan N to Westport seniors.

Frequently Asked Questions

What is a supplemental insurance agent in Westport?

A supplemental insurance agent in Westport helps you buy Medigap or Medicare Supplement plans. These agents are licensed in Connecticut and can compare plans from different carriers. They do not work for the government.

When can I enroll in a Medigap plan in Connecticut?

In Connecticut you have a six-month Medigap open enrollment period that starts when you are 65 and enrolled in Medicare Part B. During this time you cannot be denied coverage or charged more for pre-existing conditions. After this period you may face medical underwriting.

Are Medigap plans standardized in Connecticut?

Yes Medigap plans in Connecticut follow federal standards with lettered plans like A B D G K L M and N. Each plan offers the same basic benefits regardless of the insurance company. Agents can help you compare prices for the same plan across different insurers.

Supplemental Insurance Agents in Other Connecticut Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each supplemental insurance agent's credentials and current standing with your state Department of Insurance.