ADVERTISING DISCLOSURE: BeforeInsuranceUSA.com is an informational directory, not an insurance agency, broker, or licensed producer. We do not sell insurance or provide insurance advice. No agent-client relationship is created by using this site. Except where a listing is clearly marked Featured, no agent listed on this site has paid for their listing. Featured listings are paid advertisements. This is an advertisement.

Find Supplemental Insurance Agents Near You in Middletown, NY

Browse supplemental insurance agents serving Middletown, New York. Updated 2026-07-14.

The top-rated supplemental insurance agent in Middletown, New York is James Demmer - State Farm Insurance Agent, rated 4.9 stars across 924 reviews. Other highly rated options include Cassie Gleeson - State Farm Insurance Agent, Joy Insurance, Evergreen Insurance Agency -Peter Schmidt. This directory lists 18 supplemental insurance agents serving Middletown.

Showing 18 supplemental insurance agents in Middletown, NYListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1James Demmer - State Farm Insurance Agent13 James P Kelly Way ste a(845) 344-3276
2Cassie Gleeson - State Farm Insurance Agent246 NY-211(845) 775-3277
3Joy Insurance639 E Main St(845) 683-5261
4Evergreen Insurance Agency -Peter Schmidt690, 4 NY-211 E(845) 673-6127
5The Premium Select Group Inc.32 County Rd 78(845) 520-9774
6Hutchings Agency Inc.682 E Main St # 2D(845) 343-2148
7Nicole Feichtl at Comparion Insurance Agency265 NY-211 Suite 106B(845) 394-6155
8Lori Buhagiar: Allstate Insurance125 Dolson Ave Ste 22b(845) 343-5909
9Marshall+Sterling90 Crystal Run Rd(845) 343-2138
10The Lang Agency LLC22 County Rd 78 #2(845) 342-5264
JD
13 James P Kelly Way ste a
James Demmer - State Farm Insurance Agent
Supplemental Insurance Agent · Middletown, NY

James Demmer - State Farm Insurance Agent serves the Middletown, NY area and surrounding Orange County region as a supplemental insurance agent. The company helps individuals fill gaps in their primary health insurance coverage by offering policies that can assist with out-of-pocket costs. Supplemental insurance plans are designed to provide financial support for unexpected medical events. The agency regularly assists clients with enrolling in accident and hospital indemnity insurance plans.

CG
246 NY-211
Cassie Gleeson - State Farm Insurance Agent
Supplemental Insurance Agent · Middletown, NY

Cassie Gleeson - State Farm Insurance Agent in Middletown, NY provides supplemental insurance policies designed to fill gaps left by primary health coverage, helping clients manage out-of-pocket costs. The office offers guidance on plan selection and facilitates enrollment, with ongoing support for policy questions and claims assistance. Payment plan options and periodic policy reviews are available to ensure coverage remains suitable as needs change. Its supplemental insurance services are intended for single-family homes, apartments, retail businesses, and restaurants.

JI
639 E Main St
Joy Insurance
Supplemental Insurance Agent · Middletown, NY

Joy Insurance serves homeowners, renters, and small business owners in the Middletown area who seek supplemental insurance coverage to fill gaps left by major medical or property policies. The agency assists clients in selecting policies that help cover deductibles, co-pays, or income loss during unexpected events. Services focus on explaining plan options clearly so customers can make informed decisions without pressure. The agency also provides support for policy claims and renewals. Joy Insurance extends its services to residents of the nearby town of Goshen.

EI
690, 4 NY-211 E
Evergreen Insurance Agency -Peter Schmidt
Supplemental Insurance Agent · Middletown, NY
PS
32 County Rd 78
The Premium Select Group Inc.
Supplemental Insurance Agent · Middletown, NY

In the supplemental insurance field, clients choose between one-time policy setups and recurring service plans for coverage adjustments. The Premium Select Group Inc. operates in Middletown, NY, helping local residents and businesses navigate options such as accident, critical illness, or hospital indemnity policies. These supplemental plans fill gaps left by major medical insurance. The company’s service runs on an as-needed basis, with clients contacting them when their circumstances change or when they wish to review their current supplemental coverage.

HA
682 E Main St # 2D
Hutchings Agency Inc.
Supplemental Insurance Agent · Middletown, NY

As the seasons change in the Middletown area, households often review their existing health coverage to identify potential gaps. Hutchings Agency Inc. serves locals by explaining how supplemental insurance can help manage out-of-pocket expenses not covered by major medical plans. They tailor these conversations to each client’s current needs and budget. A typical first step involves a personal meeting or phone call to review the individual’s existing coverage and discuss likely financial exposures. This initial assessment helps the agency recommend appropriate policy options for further consideration.

NF
265 NY-211 Suite 106B
Nicole Feichtl at Comparion Insurance Agency
Supplemental Insurance Agent · Middletown, NY

Nicole Feichtl at Comparion Insurance Agency serves as a supplemental insurance agent based in Middletown, New York. This role involves providing Medicare supplements, critical illness plans, and hospital indemnity coverage that fill gaps left by primary major medical policies. Individualized assessments help clients address out-of-pocket expenses and uncovered deductibles. The agency offers these specialty add-on policies for various commercial sectors, including local offices, warehouses, and food service operations that need tailored group benefit solutions.

LB
125 Dolson Ave Ste 22b
Lori Buhagiar: Allstate Insurance
Supplemental Insurance Agent · Middletown, NY

Lori Buhagiar: Allstate Insurance in Middletown, NY, provides supplemental insurance policies designed to cover gaps left by primary health plans. It also handles general insurance services for local residents. The agency specializes in helping clients manage out-of-pocket medical costs, offering accident and critical illness coverage that pays cash benefits directly to policyholders. As winter approaches, it assists individuals in reviewing their existing plans to ensure adequate protection against seasonal injuries like fractures or hospital stays that can strain household budgets.

MS
90 Crystal Run Rd
Marshall+Sterling
Supplemental Insurance Agent · Middletown, NY

Marshall+Sterling serves households in Middletown by identifying supplemental insurance policies that address gaps in primary health coverage. The agency also assists local businesses with commercial plans to protect against unexpected medical expenses and lost income. Their services extend throughout the surrounding area, providing consultations tailored to individual needs and budgets. Regular check-ins with existing clients allow the agency to adjust coverage as circumstances change, with follow-up calls and policy reviews scheduled between routine visits to maintain appropriate protection.

LA
22 County Rd 78 #2
The Lang Agency LLC
Supplemental Insurance Agent · Middletown, NY

The Lang Agency LLC serves residents of Middletown and the surrounding region by providing supplemental insurance policies that help cover costs not paid by primary health plans. These policies can include options for accident, cancer, and critical illness coverage. The agency also assists local businesses by offering similar supplemental plans to their employees, ensuring broader access within the community. Between regular visits from primary carriers, the agency maintains contact with policyholders to facilitate seamless claim submissions and adjust coverage as life circumstances change.

MI
593 NY-211
Macri Isola Catherine Insurance Agency Inc.
Supplemental Insurance Agent · Middletown, NY
(845) 692-2277
cmiinsuranceagency.com
RI
112 North St
Reineke Insurance Agency
Supplemental Insurance Agent · Middletown, NY
(845) 343-8000
curabba.com/reineke-insurance-agency
MI
610 Route 211 E, Ste 2
The Misner Insurance Agency, Inc.
Supplemental Insurance Agent · Middletown, NY
(845) 434-7755
misneragency.com
EI
117 North St
Estrella Insurance
Supplemental Insurance Agent · Middletown, NY
(845) 535-0095
agents.estrellainsurance.com/en-us/ny/middletown/402.html
EH
85 Crystal Run Rd
Elevance Health
Supplemental Insurance Agent · Middletown, NY
elevancehealth.com
JD
225 Dolson Ave #304
Jason D Hartman - Aflac Insurance Agent
Supplemental Insurance Agent · Middletown, NY
(845) 381-1184
NI
1934 NY-211
Nationwide Insurance: Vogel And Moore Inc.
Supplemental Insurance Agent · Middletown, NY
(845) 692-4441
agency.nationwide.com/ny/middletown/10941/vogel-and-moore-inc
AA
633 NY-211
Affinity Advantage Financial Solutions
Supplemental Insurance Agent · Middletown, NY
(845) 695-1000
affinityadvantage.com

What Does a a Supplemental Insurance Agent in Middletown Cost?

Supplemental insurance agent services are usually free to consumers because agents earn commissions from insurance carriers. Medigap plan premiums in New York can range from about $100 to $400 per month depending on your age, location, and plan type. Costs vary by case. This is general information, not insurance advice.

About supplemental insurance agents in Middletown

Supplemental insurance agents in Middletown, NY help residents choose Medigap or Medicare Advantage plans that fill gaps in Original Medicare. New York law guarantees a 30-day open enrollment period for Medigap policies when you first turn 65. Agents also explain how state regulations affect plan availability and pricing in Orange County.

Frequently Asked Questions

What is a supplemental insurance agent in Middletown NY?

A supplemental insurance agent is a licensed professional who helps you compare and enroll in Medigap or Medicare Advantage plans. They work with multiple carriers to find a plan that fits your health needs and budget. Agents must follow New York State Department of Financial Services rules.

When can I enroll in a Medigap plan in New York?

In New York, you have a 6-month Medigap open enrollment period starting the month you turn 65 and enroll in Medicare Part B. During this time, you can buy any Medigap policy without medical underwriting. Outside this window, insurers may use health questions to set premiums.

Are there special rules for Medicare Advantage in New York?

Yes, New York allows a 12-month trial period for Medicare Advantage plans. If you join a Medicare Advantage plan when first eligible, you can switch back to Original Medicare and buy a Medigap policy within the first year. This rule helps protect your rights.

Supplemental Insurance Agents in Other New York 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.