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Find Supplemental Insurance Agents Near You in Redwood City, CA

Browse supplemental insurance agents serving Redwood City, California. Updated 2026-07-14.

The top-rated supplemental insurance agent in Redwood City, California is Cost-U-Less Insurance, rated 4.9 stars across 544 reviews. Other highly rated options include Charlotte Russell - State Farm Insurance Agent, Divia Express Insurance Agency, Inc., Steve Fiorentino - State Farm Insurance Agent. This directory lists 19 supplemental insurance agents serving Redwood City.

Showing 19 supplemental insurance agents in Redwood City, CAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Cost-U-Less Insurance660 Price Ave Unit A(650) 389-9052
2Charlotte Russell - State Farm Insurance Agent1391 Woodside Rd Ste 218(650) 369-7900
3Divia Express Insurance Agency, Inc.3000 Middlefield Rd(650) 299-1111
4Steve Fiorentino - State Farm Insurance Agent734 Woodside Rd(650) 322-3499
5Willow Street Insurance2103 Middlefield Rd(650) 298-8111
6U D Side Insurance&Middlefield registration services3133 Middlefield Rd # A(650) 306-9185
7Fiesta Auto Insurance & Tax Service3050 Middlefield Rd(650) 381-9467
8CB Acker Associates Insurance Services501 Seaport Ct #101(650) 969-5844
9CIS Insurance Agency171 Fifth Ave #102(408) 746-5030
10Stone Meadow Benefits & Insurance Associates50 Woodside Rd(650) 456-7904
CU
660 Price Ave Unit A
Cost-U-Less Insurance
Supplemental Insurance Agent · Redwood City, CA

Cost-U-Less Insurance serves Redwood City and the surrounding communities of the San Francisco Peninsula, specializing in supplemental insurance agent services. The company handles a range of ancillary policies, including Medicare supplements, hospital indemnity plans, and critical illness coverage for local residents. Its general approach involves reviewing individual coverage gaps from standard health plans and presenting policy options that fit a client’s budget and specific needs. This office typically works through a straightforward consultation that tailors each supplemental package to the customer’s existing medical situation.

CR
1391 Woodside Rd Ste 218
Charlotte Russell - State Farm Insurance Agent
Supplemental Insurance Agent · Redwood City, CA

Charlotte Russell - State Farm Insurance Agent in Redwood City, California provides supplemental insurance coverage designed to fill gaps left by major medical plans. Its service options include personalized policy reviews and claim assistance, helping clients navigate health-related financial uncertainties. The agency’s maintenance plans involve annual check-ins to adjust coverage as life circumstances change. It services a variety of properties including single-family homes, apartments, retail storefronts, and local restaurants.

DE
3000 Middlefield Rd
Divia Express Insurance Agency, Inc.
Supplemental Insurance Agent · Redwood City, CA

Divia Express Insurance Agency, Inc. serves residents throughout San Mateo County and the Redwood City area as a supplemental insurance agent. It assists clients in bridging gaps left by major medical plans, offering policies designed to cover out-of-pocket expenses like deductibles and coinsurance. The agency helps customers secure financial protection through accident and critical illness coverage, ensuring unforeseen health events do not lead to significant personal costs.

SF
734 Woodside Rd
Steve Fiorentino - State Farm Insurance Agent
Supplemental Insurance Agent · Redwood City, CA

Steve Fiorentino’s agency serves Redwood City homeowners, renters, and small business owners who seek supplemental insurance coverages. These policies help fill gaps left by standard plans, often addressing specific needs like accident recovery or critical illness expenses. The agency also assists property managers with policies tailored for rental properties and loss-of-income scenarios. Clients needing extra protection for dental, vision, or short-term disability can find guidance here. In addition to serving the greater Peninsula area, the agency covers communities extending toward San Carlos and Atherton.

WS
2103 Middlefield Rd
Willow Street Insurance
Supplemental Insurance Agent · Redwood City, CA

Willow Street Insurance serves Redwood City and the surrounding communities of San Mateo County, offering supplemental insurance policies that fill gaps left by traditional health plans. It handles Medicare supplements, accident, critical illness, and hospital indemnity coverage tailored to individual needs. Clients receive clear explanations of how these plans coordinate with primary insurance to reduce out-of-pocket costs. The company reviews each customer’s existing coverage and medical history before recommending options, then manages the application process and enrollment from start to finish to ensure accurate policy activation.

UD
3133 Middlefield Rd # A
U D Side Insurance&Middlefield registration services
Supplemental Insurance Agent · Redwood City, CA

U D Side Insurance&Middlefield registration services provides both one-time policy reviews and ongoing enrollment support for supplemental coverage. Their focus includes Medicare supplements, accident, and hospital indemnity plans that help bridge gaps in primary insurance. Operating as a supplemental insurance agent in Redwood City, CA, the company addresses the specific needs of local residents. Clients may schedule a single consultation, establish regular check-ins, or request assistance on an as-needed basis for plan changes or annual open enrollment.

FA
3050 Middlefield Rd
Fiesta Auto Insurance & Tax Service
Supplemental Insurance Agent · Redwood City, CA

For supplemental insurance, clients choose between a single-policy purchase or recurring plans that adjust with changing needs. In Redwood City, Fiesta Auto Insurance & Tax Service offers options to cover gaps in primary health coverage, such as accident, critical illness, or hospital indemnity plans. These policies complement existing benefits and help manage out-of-pocket costs. Service is available on either a one-time or as-needed basis, allowing clients to sign up when a specific need arises.

CA
501 Seaport Ct #101
CB Acker Associates Insurance Services
Supplemental Insurance Agent · Redwood City, CA

CB Acker Associates Insurance Services in Redwood City offers supplemental health and life coverage options that fill gaps in primary insurance policies. It assists clients with selecting Medicare supplements, accident plans, and hospital indemnity policies tailored to individual needs. The agency serves local residents seeking to reduce out-of-pocket medical costs and protect against unexpected financial burdens. It provides particular help during the Annual Enrollment Period when seniors may need guidance adjusting their Medicare supplement plans for the upcoming year.

CI
171 Fifth Ave #102
CIS Insurance Agency
Supplemental Insurance Agent · Redwood City, CA

Redwood City residents often reassess health costs after open enrollment or a life change. CIS Insurance Agency assists by focusing solely on supplemental insurance products that fill gaps in standard coverage. This local agent helps clients explore policies for accident, critical illness, or hospital indemnity needs. They provide clear comparisons of different plan options available to individuals and families across the area. The process begins with a no-obligation review of existing coverage to identify specific gaps. An agent then schedules a straightforward assessment of the client’s current situation.

SM
50 Woodside Rd
Stone Meadow Benefits & Insurance Associates
Supplemental Insurance Agent · Redwood City, CA

Stone Meadow Benefits & Insurance Associates, located in Redwood City, CA, works as a supplemental insurance agent. The firm specializes in helping individuals fill critical gaps often left by major medical plans. These optional add-ons can include coverage for accidents, critical illness, or hospital stays. For local businesses, the agency provides groups with access to such tailored benefits. It regularly serves the needs of offices, warehouses, and food service operations seeking voluntary supplemental coverage for their employees.

DN
734 Woodside Rd
Darren Normoyle - State Farm Insurance Agent
Supplemental Insurance Agent · Redwood City, CA
(650) 257-7848
darrennormoyle.com
RC
855 Jefferson Ave #2669
Red Cedar Insurance Agency
Supplemental Insurance Agent · Redwood City, CA
(844) 733-2332
redcedaragency.com
BT
3125 Middlefield Rd
BAY TECH INSURANCE SERVICES
Supplemental Insurance Agent · Redwood City, CA
(650) 260-2218
baytechinsurance.com
GI
20 El Camino Real
Gordon Insurance
Supplemental Insurance Agent · Redwood City, CA
(650) 654-5555
gordoninsurance.com
RI
390 Bridge Pkwy
Roman Ivlev Medicare Insurance Services
Supplemental Insurance Agent · Redwood City, CA
(415) 744-4930
sparkadvisors.com/agents/roman-ivlev-7012
RC
1622 Hudson St
Redwood City Insurance Center
Supplemental Insurance Agent · Redwood City, CA
(650) 365-8800
redwoodcityinsurance.com
BI
20 El Camino Real
Barrett Insurance Services
Supplemental Insurance Agent · Redwood City, CA
(650) 619-0370
barrettinsuranceservices.weebly.com
WI
1733 Woodside Rd Suite 370
Woodside Insurance Services LLC
Supplemental Insurance Agent · Redwood City, CA
(650) 529-9204
woodsideinsurance.net
BA
3 Lagoon Dr #260
Bay Area Insurance Inc
Supplemental Insurance Agent · Redwood City, CA
(650) 654-9750
bai-online.com

What Does a a Supplemental Insurance Agent in Redwood City Cost?

Supplemental insurance agent services in California are typically free to consumers because agents earn commissions from insurance carriers. Medigap plan premiums in Redwood City range from about 100 to 350 dollars per month depending on the plan type and your age. Some plans may have higher premiums for older applicants. Costs vary by case. This is general information not insurance advice.

About supplemental insurance agents in Redwood City

Supplemental insurance agents in Redwood City help clients navigate Medicare Supplement plans and other gap coverage options. California law requires agents to be licensed by the California Department of Insurance and to follow strict disclosure rules. Local agents can explain how plans like Medigap work alongside Original Medicare for Redwood City residents.

Frequently Asked Questions

What does a supplemental insurance agent in Redwood City do?

A supplemental insurance agent helps you compare and enroll in Medicare Supplement plans also called Medigap. They explain the differences between Plan A through Plan N and help you find a plan that fits your budget and medical needs. Agents in California must be licensed and may offer policies from multiple carriers.

When can I enroll in a Medicare Supplement plan in California?

The best time to enroll is during your Medigap Open Enrollment Period which starts when you are 65 and enrolled in Medicare Part B. This period lasts six months. During this time California law guarantees you can buy any Medigap policy without medical underwriting.

Are there California rules about Medigap pricing?

Yes California requires Medigap policies to be either community rated or issue age rated. Community rated policies charge the same premium regardless of age. Issue age rated policies base the premium on your age at purchase. Agents must clearly explain the rating method before you buy.

Supplemental Insurance Agents in Other California 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.