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HomeMedicare Insurance AgentsNew York › New Windsor

Find Medicare Insurance Agents Near You in New Windsor, NY

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

The top-rated medicare insurance agent in New Windsor, New York is Phillip Williams - State Farm Insurance Agent, rated 5.0 stars across 974 reviews. Other highly rated options include JMD Insurance Agency, Steve Cooney - State Farm Insurance Agent, Roger Dwyer: Allstate Insurance. This directory lists 13 medicare insurance agents serving New Windsor.

Showing 13 medicare insurance agents in New Windsor, NYListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Phillip Williams - State Farm Insurance Agent164 Temple Hill Rd #300(845) 563-7100
2JMD Insurance Agency357 Windsor Hwy #300(845) 391-8646
3Steve Cooney - State Farm Insurance Agent316 Blooming Grove Turnpike 94 Suite 200(845) 562-6400
4Roger Dwyer: Allstate Insurance357 Windsor Hwy(845) 562-1664
5Windgate Insurance Agency, Inc.375 Windsor Hwy #500(845) 562-8800
6Dalleo Group Insurance161 Windsor Hwy STE 200(845) 565-1516
7New York Life Insurance460 Temple Hill Rd(845) 569-8200
8Bryan Insurance Agency, LLC287 Windsor Hwy #350(845) 565-2200
9American National Insurance Company/Fam Family Insurance Company88 Old Rte 9W suite 100(845) 562-0701
10Jannotti Insurance Agency20 Brown's Dr(845) 564-2942
PW
164 Temple Hill Rd #300
Phillip Williams - State Farm Insurance Agent
Medicare Insurance Agent · New Windsor, NY

Phillip Williams - State Farm Insurance Agent serves the New Windsor, NY area and the surrounding Orange County region as a Medicare insurance agent. The company helps residents navigate their healthcare coverage options during enrollment periods. Understanding the complexities of Original Medicare and private plans, clients receive guidance tailored to their individual needs and budgets. The agency focuses on educating customers so they can make informed decisions about their coverage. Specific services provided include assisting with Medicare Supplement plans and Medicare Advantage plan comparisons.

JI
357 Windsor Hwy #300
JMD Insurance Agency
Medicare Insurance Agent · New Windsor, NY

JMD Insurance Agency provides a range of Medicare insurance services in New Windsor, NY, including plan comparisons and enrollment assistance. It offers ongoing support to help clients review their coverage during annual enrollment periods and navigate any changes in their healthcare needs. The agency works with individuals seeking to understand their Medicare options, ensuring they receive guidance tailored to their situation. It services single-family homes, apartments, retail, and restaurants.

SC
316 Blooming Grove Turnpike 94 Suite 200
Steve Cooney - State Farm Insurance Agent
Medicare Insurance Agent · New Windsor, NY

Steve Cooney - State Farm Insurance Agent serves homeowners, renters, and small business owners. As a Medicare insurance agent in New Windsor, New York, this agency helps clients navigate plan options, enrollment periods, and coverage details for their healthcare needs. Clear explanations and personalized guidance are offered to individuals approaching or over age sixty-five who seek suitable Medicare plans. The agency also serves residents throughout Orange County and the surrounding Hudson Valley communities, including the neighboring town of Newburgh.

RD
357 Windsor Hwy
Roger Dwyer: Allstate Insurance
Medicare Insurance Agent · New Windsor, NY

Serving the greater New Windsor, New York area and surrounding communities, this company provides guidance on Medicare insurance options. It helps clients navigate Medicare Supplement plans, Advantage plans, and Part D prescription drug coverage to address individual healthcare needs. The agency explains the annual enrollment periods and how to compare various plan benefits and costs. To handle a typical job, it starts by assessing a client’s current health, budget, and preferred providers, then presents a short list of suitable plan choices for the client to consider.

WI
375 Windsor Hwy #500
Windgate Insurance Agency, Inc.
Medicare Insurance Agent · New Windsor, NY

Windgate Insurance Agency, Inc. in New Windsor, NY helps individuals distinguish between one-time enrollment periods and the ongoing adjustments available during annual open enrollment. Their work focuses on explaining how Medicare Advantage plans and Supplement policies differ in coverage scope and cost structure. Assistance is provided on a one-time or as-needed basis, depending on whether the client is new to Medicare or reviewing their existing plan during a scheduled change period.

DG
161 Windsor Hwy STE 200
Dalleo Group Insurance
Medicare Insurance Agent · New Windsor, NY

Dalleo Group Insurance specializes in guiding clients through Medicare Advantage plans and Part D drug coverage. Serving the New Windsor, NY area, this agency provides straightforward assistance in navigating annual enrollment periods and comparing plan options. It helps individuals identify supplemental coverage that aligns with their current healthcare needs and budget constraints. The company also addresses the specific concerns that arise during Medicare’s Open Enrollment, ensuring clients can make timely adjustments before the year-end deadline.

NY
460 Temple Hill Rd
New York Life Insurance
Medicare Insurance Agent · New Windsor, NY

During Medicare’s Annual Enrollment Period, residents in the New Windsor area often need clear guidance through plan changes and prescription drug coverage options. New York Life Insurance helps local beneficiaries compare Medicare Advantage and Supplement plans in simple, straightforward terms. Their agents take time to explain how different policies coordinate with existing coverage and out-of-pocket costs. An initial assessment meeting reviews personal health needs and current insurance details. That meeting concludes with a plain-language evaluation of each plan’s suitability for the coming year.

BI
287 Windsor Hwy #350
Bryan Insurance Agency, LLC
Medicare Insurance Agent · New Windsor, NY

Bryan Insurance Agency, LLC provides guidance on Medicare insurance options for individuals in New Windsor, New York. The agency specializes in explaining the various Medicare Supplement plans and Part D prescription drug coverage available to eligible residents. It helps clients navigate the annual enrollment periods and choose appropriate plans based on their healthcare needs. The agency can serve offices, warehouses, and food service businesses seeking to understand their Medicare-related options.

AN
88 Old Rte 9W suite 100
American National Insurance Company/Fam Family Insurance Company
Medicare Insurance Agent · New Windsor, NY

American National Insurance Company and Fam Family Insurance Company provides residential Medicare insurance guidance to individuals in New Windsor, New York. The agency also supports commercial coverage options for local small businesses needing group health solutions. Their service area includes New Windsor and surrounding communities across Orange County. Clients receive thorough plan comparisons during initial consultations, with follow-up support available between regular visits to address coverage changes or upcoming enrollment periods.

JI
20 Brown's Dr
Jannotti Insurance Agency
Medicare Insurance Agent · New Windsor, NY

Jannotti Insurance Agency is a licensed Medicare insurance agent located in New Windsor, New York, recognized for guiding clients through the complexities of Medicare plans. The agency assists individuals with navigating coverage options, including Medicare Advantage, Part D prescription drug plans, and Medicare Supplement policies. By evaluating each client’s unique healthcare needs, the team helps compare available plans in the region to find suitable choices. The agency also offers specialized support for enrollment periods, ensuring clients understand deadlines and can make timely decisions about their coverage.

DJ
161 Windsor Hwy STE 200
Dalleo Jr Joseph M
Medicare Insurance Agent · New Windsor, NY
(845) 565-1516
AH
345 Windsor Hwy
Auto | Home | Life
Medicare Insurance Agent · New Windsor, NY
(845) 360-2408
insurancenyquote.com/contact-us
KJ
460 Temple Hill Rd
Kevin J. Mulqueen, Financial Advisor - Eagle Strategies
Medicare Insurance Agent · New Windsor, NY
(845) 563-9325
kevinmulqueen.net

What Does a a Medicare Insurance Agent in New Windsor Cost?

Medicare insurance agents in New York do not charge you a fee for their services. Their compensation comes from insurance carriers. Plan costs vary by type: Medicare Advantage plans often have $0 premiums, while Medigap plans can cost between $100 and $400 per month depending on your age and location. Part D prescription plans average $30 to $100 per month. This is general information and not insurance advice.

About medicare insurance agents in New Windsor

Medicare insurance agents in New Windsor, New York help residents compare Part D, Medicare Advantage, and Medigap plans. New York law requires agents to be licensed by the Department of Financial Services. Local agents can explain how New York-specific rules like the guaranteed issue period for Medigap apply to you.

Frequently Asked Questions

What is the role of a Medicare insurance agent in New Windsor?

A Medicare insurance agent helps you review plan options, compare costs, and enroll in coverage that fits your needs. They are licensed by New York State and must follow state regulations. Agents do not charge you directly; they are paid by insurance companies.

When can I enroll in Medicare in New Windsor?

You can enroll during your Initial Enrollment Period which starts three months before you turn 65 and ends three months after. New York also has a Special Enrollment Period for certain life events. Missing deadlines may result in late penalties.

Are there New York-specific rules for Medigap plans?

Yes, New York has a guaranteed issue rule for Medigap plans. This means you can buy a Medigap policy at any time of year without medical underwriting if you are in your trial period or lose other coverage. This rule is unique to New York.

Medicare Insurance Agents in Other New York 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.