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Find Medicare Insurance Agents Near You in Windsor, CT

Browse medicare insurance agents serving Windsor, Connecticut. Updated 2026-07-14.

The top-rated medicare insurance agent in Windsor, Connecticut is Lynn Dobrowsky - State Farm Insurance Agent, rated 5.0 stars across 339 reviews. Other highly rated options include Oxygen Insurance Agency LLC, Bolton Financial, LLC - Helping Connecticut retirees optimize pensions, Social Security, and retirement income, The Hartford. This directory lists 15 medicare insurance agents serving Windsor.

Showing 15 medicare insurance agents in Windsor, CTListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Lynn Dobrowsky - State Farm Insurance Agent150 Poquonock Ave(860) 640-6777
2Oxygen Insurance Agency LLC360 Bloomfield Ave Suite 301(860) 580-6226
3Bolton Financial, LLC - Helping Connecticut retirees optimize pensions, Social Security, and retirement income100 Northfield Dr #200(860) 298-1011
4The Hartford1 Griffin Rd N(860) 547-5000
5Brian Busam - State Farm Insurance Agent555 Day Hill Rd(860) 787-5415
6Allstate - Gridley Insurance181 Broad St Ste 2(860) 602-6456
7Parker Ellingwood Agency Inc Insurance62 Poquonock Ave # 5(860) 688-5215
8The Hanover Insurance Group Regional Office7 Waterside Crossing Suite 101(860) 368-5030
9Farmers Insurance - Louis Pinnock65 Maple Ave fl 1(860) 787-5777
10Rabbett Insurance Agency233 Addison Rd(860) 688-1303
LD
150 Poquonock Ave
Lynn Dobrowsky - State Farm Insurance Agent
Medicare Insurance Agent · Windsor, CT

Lynn Dobrowsky - State Farm Insurance Agent serves the Windsor, Connecticut area as a Medicare insurance agency. It helps clients understand their options and select appropriate coverage plans for their healthcare needs. The company assists individuals navigating enrollment periods and comparing different Medicare policies. Specific services handled in this area include explaining Medicare Supplement plans to fill gaps in original Medicare and managing the transition from employer-based insurance to Medicare coverage.

OI
360 Bloomfield Ave Suite 301
Oxygen Insurance Agency LLC
Medicare Insurance Agent · Windsor, CT

Oxygen Insurance Agency LLC provides Medicare insurance guidance and enrollment services to individuals in Windsor, CT. It helps clients navigate initial eligibility, plan selection, and ongoing coverage needs. The agency assists with reviewing annual policy changes and ensuring plans remain aligned with personal healthcare requirements. It also coordinates service for supplemental and prescription drug plan options. Oxygen Insurance Agency LLC services single-family homes, apartments, retail establishments, and restaurants, offering Medicare support to local residents and business owners alike.

BF
100 Northfield Dr #200
Bolton Financial, LLC - Helping Connecticut retirees optimize pensions, Social Security, and retirement income
Medicare Insurance Agent · Windsor, CT

Bolton Financial, LLC helps Connecticut retirees and those approaching retirement navigate Medicare options, pension strategies, and Social Security or retirement income decisions from its base in Windsor. As a Medicare insurance agent, the agency assists clients in selecting appropriate health coverage and coordinating benefits with other retirement resources. It also provides guidance on how to structure pensions and other income streams alongside Medicare plans. The company serves clients throughout the greater Hartford metro area, including neighboring communities such as Bloomfield.

HA
1 Griffin Rd N
The Hartford
Medicare Insurance Agent · Windsor, CT

The Hartford serves the Windsor, Connecticut metro area as a local Medicare Insurance Agent. The company helps clients navigate Medicare plan options, including enrollment and annual coverage reviews. Agents explain program differences and assist with plan changes during open enrollment periods. They also guide individuals through Medicare Supplement and Medicare Advantage choices to match healthcare needs. The agency handles Part D prescription drug plan selections and coordination with existing coverage.

BB
555 Day Hill Rd
Brian Busam - State Farm Insurance Agent
Medicare Insurance Agent · Windsor, CT

Serving Windsor, Connecticut, and the surrounding communities, Brian Busam - State Farm Insurance Agent handles Medicare insurance needs for eligible individuals in the area. The agency helps clients navigate plan options, enrollment periods, and coverage details related to Medicare. Each job is approached by first reviewing the client’s personal healthcare requirements and existing coverage before comparing available plans to identify a suitable option for their situation.

AG
181 Broad St Ste 2
Allstate - Gridley Insurance
Medicare Insurance Agent · Windsor, CT

At Allstate - Gridley Insurance in Windsor, CT, the distinction between one-time plan selection and recurring annual policy reviews is central to Medicare insurance agent work. Agents help navigate initial enrollment coverage decisions during specific enrollment windows. They later assist with adjusting plans as healthcare needs or costs change each year. Ongoing service for these coverage options typically runs on a scheduled or as-needed basis, depending on approaching deadlines or client notifications.

PE
62 Poquonock Ave # 5
Parker Ellingwood Agency Inc Insurance
Medicare Insurance Agent · Windsor, CT

As Medicare open enrollment nears each fall, residents of Windsor, Connecticut, seek help navigating plan changes and increasing Part D costs. Parker Ellingwood Agency Inc Insurance provides local medicare insurance agent services, assisting clients in comparing Medicare Advantage and Supplement options. Their guidance helps ensure coverage aligns with individual prescriptions and healthcare budgets. A complimentary initial assessment is offered, during which Medicare cards and current medications are reviewed.

HI
7 Waterside Crossing Suite 101
The Hanover Insurance Group Regional Office
Medicare Insurance Agent · Windsor, CT

The Hanover Insurance Group Regional Office in Windsor, CT provides guidance on Medicare Advantage plans, prescription drug coverage, and Medigap policies. Its agents assist clients in understanding plan options and navigating annual enrollment periods. The office helps individuals compare available coverage to meet specific healthcare needs and budgets. A key service involves addressing the initial enrollment period for those turning 65, ensuring timely sign-up to avoid late penalties.

FI
65 Maple Ave fl 1
Farmers Insurance - Louis Pinnock
Medicare Insurance Agent · Windsor, CT

Farmers Insurance - Louis Pinnock assists Windsor, CT residents with their Medicare insurance needs, helping them navigate plan options and enrollment periods. This agency specializes in Medicare supplement and Advantage plan guidance, ensuring clients understand available coverage. Personal consultations clarify complex policy details, supporting informed decision-making for healthcare coverage. The agency can serve local small businesses requiring employee health benefit coordination, as well as commercial accounts in offices, warehouses, and food service operations.

RI
233 Addison Rd
Rabbett Insurance Agency
Medicare Insurance Agent · Windsor, CT

Rabbett Insurance Agency serves residents of Windsor, Connecticut, by helping them navigate Medicare plan options for their healthcare needs. The agency also assists local businesses with commercial insurance coverage, offering tailored solutions for different industries throughout the area. Their agents guide clients through annual enrollment changes and answer questions about plan benefits, deductibles, and provider networks. After an initial consultation, clients can return for follow-up help during the Medicare open enrollment period or whenever a change in health status requires a review between regular plan visits.

MA
360 Bloomfield Ave #202
Mary Adams
Medicare Insurance Agent · Windsor, CT
(860) 602-4281
AG
181 Broad St ste 2
Allstate - Gridley Insurance Team
Medicare Insurance Agent · Windsor, CT
(860) 602-6456
agents.allstate.com/gridley-insurance-team-windsor-ct1.html
NS
100 Northfield Dr Ste 200
Neerab Shrestha, Agent - New York Life
Medicare Insurance Agent · Windsor, CT
(860) 298-1038
neerab.com
FF
360 Bloomfield Ave Suite 301
Family First Life - Christian Baer
Medicare Insurance Agent · Windsor, CT
(860) 327-2327
JJ
100 Northfield Dr #200
James Joseph Pointek - New York Life Insurance
Medicare Insurance Agent · Windsor, CT
(781) 864-8347
newyorklife.com/agent/jjpointek

What Does a a Medicare Insurance Agent in Windsor Cost?

Medicare insurance agents in Connecticut typically do not charge a fee to consumers. Agent compensation is built into the plan premiums you pay. Monthly premiums for Medicare Advantage plans in the Windsor area can range from zero to over 100 dollars depending on the plan. Medigap premiums vary by age health and plan type. This is general information and not insurance advice.

About medicare insurance agents in Windsor

Medicare insurance agents in Windsor Connecticut help residents compare Medicare Advantage Medigap and Part D plans. Connecticut law requires agents to be licensed by the state and follow specific marketing rules. Working with a local agent can simplify your enrollment and annual plan review.

Frequently Asked Questions

When can I enroll in Medicare in Windsor Connecticut?

Your Initial Enrollment Period starts three months before you turn 65 and lasts seven months. Connecticut residents also have an Annual Enrollment Period from October 15 to December 7 each year.

What is the difference between Medicare Advantage and Medigap in Connecticut?

Medicare Advantage plans replace Original Medicare and often include drug coverage. Medigap plans supplement Original Medicare and help pay for deductibles and copays. Connecticut guarantees Medigap access during your Medigap Open Enrollment Period.

Do Medicare insurance agents in Windsor charge fees for their services?

Most Medicare insurance agents in Connecticut are paid by insurance companies and do not charge clients directly. You should confirm the agents compensation structure before working with them.

Medicare Insurance Agents in Other Connecticut 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.