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Find Life Insurance Agents Near You in Winchester, MA

Browse life insurance agents serving Winchester, Massachusetts. Updated 2026-07-14.

The top-rated life insurance agent in Winchester, Massachusetts is Scotti Insurance Agency, rated 4.3 stars across 14 reviews. Other highly rated options include Saltmarsh Insurance Agency, John A Pierce Insurance Inc, W Allan Wilde & Son Insurance Agency, Inc.. This directory lists 11 life insurance agents serving Winchester.

Showing 11 life insurance agents in Winchester, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Scotti Insurance Agency19 Mt Vernon St(781) 729-9200
2Saltmarsh Insurance Agency751 Main St(781) 729-4615
3John A Pierce Insurance Inc934 Main St(781) 729-8770
4W Allan Wilde & Son Insurance Agency, Inc.887 Main St #1911(781) 729-1400
5Horace Mann Insurance Co895 Main St(781) 368-9029
6Furey Insurance28 Church St #8(781) 721-5758
7Barry & McHugh Insurance Inc10 Skillings Rd(781) 729-6600
8BARRY FREEMAN895 Main St(781) 368-9029
9Jay M Finn Insurance10 Skillings Rd(781) 729-5724
10Black Horse Insurance175 Washington St # C24(781) 729-1164
SI
19 Mt Vernon St
Scotti Insurance Agency
Life Insurance Agent · Winchester, MA

Scotti Insurance Agency serves Winchester and the broader Middlesex County area as a local life insurance agent. The firm assists residents with evaluating their long-term financial protection needs through term and permanent life insurance policies. Their work involves helping clients understand how coverage can support beneficiaries and estate plans. The agency also provides guidance on final expense policies and annuities for retirement income planning.

SI
751 Main St
Saltmarsh Insurance Agency
Life Insurance Agent · Winchester, MA

Saltmarsh Insurance Agency in Winchester, MA offers a full range of life insurance products designed to protect individuals and families from financial uncertainty. Their service approach includes helping clients assess coverage needs through personalized consultations and maintaining policies to adapt to changing life circumstances. The agency supports clients with single-family homes requiring estate planning, apartments needing income protection for tenants, and restaurants seeking key-person or buy-sell coverage, as well as retail establishments.

JP
934 Main St
John A Pierce Insurance Inc
Life Insurance Agent · Winchester, MA

Homeowners, families, and small business owners in Winchester, MA, turn to John A Pierce Insurance Inc for personal life insurance policies. Agents help clients assess coverage needs and navigate policy options from multiple carriers to secure financial protection for loved ones. The firm also serves residents in nearby Medford, ensuring individuals across the greater Boston area have access to professional life insurance guidance.

WA
887 Main St #1911
W Allan Wilde & Son Insurance Agency, Inc.
Life Insurance Agent · Winchester, MA

Serving Winchester and the surrounding communities in eastern Massachusetts, W Allan Wilde & Son Insurance Agency, Inc. specializes in life insurance. The agency helps individuals and families secure financial protection for their loved ones by offering various policy options. Each client’s unique needs and future goals are carefully reviewed to find suitable coverage. The agency undergoes a thorough fact-finding process to assess income needs and long-term obligations before recommending a policy.

HM
895 Main St
Horace Mann Insurance Co
Life Insurance Agent · Winchester, MA

Horace Mann Insurance Co specializes in life insurance planning for educators and public sector employees in Winchester, Massachusetts. The agency works closely with clients to evaluate protection needs, assisting with policy selection for income replacement and final expenses. It supports residents in managing financial security through individual consultations on coverage amounts and beneficiary designations. As school years begin each autumn, the agency helps new teachers and staff integrate appropriate life insurance options into their professional benefits portfolios.

FI
28 Church St #8
Furey Insurance
Life Insurance Agent · Winchester, MA

Furey Insurance in Winchester, MA offers both one-time policy reviews for single coverage needs and ongoing relationship-based service for clients who prefer recurring annual consultations. Their work focuses on matching individuals with appropriate life insurance plans that address long-term financial protection goals. The service is available on either a one-time basis for a specific policy purchase or an as-needed schedule for periodic reassessments of coverage requirements as circumstances change.

BM
10 Skillings Rd
Barry & McHugh Insurance Inc
Life Insurance Agent · Winchester, MA

As the leaves change in Winchester, many families begin reviewing their financial plans for the year ahead. Barry & McHugh Insurance Inc helps local residents evaluate their life insurance options to secure peace of mind during this seasonal check-in. The agency serves individuals who want to protect loved ones from unexpected financial burdens. Their process begins with an initial assessment to understand a client's specific coverage needs and budget, followed by a thorough inspection of existing policies before recommending any changes.

BF
895 Main St
BARRY FREEMAN
Life Insurance Agent · Winchester, MA

BARRY FREEMAN specializes in term life insurance policies designed for income replacement and final expense coverage, while also guiding clients through more permanent whole life options for long-term financial security. Serving Winchester, MA, this agency works with individuals and families to assess their current protection needs and future obligations. As local housing markets shift or fall mortgage rates change, adjusting a homeowner’s existing life coverage to match new loan terms becomes an essential yearly consideration.

JM
10 Skillings Rd
Jay M Finn Insurance
Life Insurance Agent · Winchester, MA

Jay M Finn Insurance provides life insurance coverage to individuals and families in Winchester, Massachusetts, specializing in tailored policy options to meet diverse financial protection needs. The agency works with clients to understand their long-term goals and select appropriate term or permanent plans. For commercial operations, it also offers business-related insurance solutions, serving local offices, warehouses, and food service establishments with appropriate coverage structures.

BH
175 Washington St # C24
Black Horse Insurance
Life Insurance Agent · Winchester, MA

Black Horse Insurance serves residential clients in Winchester, Massachusetts and also offers life insurance coverage for commercial businesses nearby. The agency assists local families with term, whole, and universal life policies to secure financial protection. Business owners can consult on key person and buy-sell coverage for their operations. The office provides ongoing support by reviewing client policies during annual check-ins and adjusting plans as needs change, ensuring consistent follow-up service between regular visits.

DI
10 Skillings Rd
Ducey Insurance Agency
Life Insurance Agent · Winchester, MA
(781) 235-6795

What Does a a Life Insurance Agent in Winchester Cost?

Life insurance costs in Massachusetts vary by age health coverage amount and policy type. A typical term life policy for a healthy 35 year old might range from 20 to 50 dollars per month for 500 thousand dollars of coverage. Whole life policies often cost 5 to 10 times more than term for the same face amount. This is general information and not insurance advice.

About life insurance agents in Winchester

Life insurance agents in Winchester Massachusetts help residents choose coverage that protects their families and meets state regulations. Massachusetts requires a license for all life insurance agents and mandates that policyholders receive a free look period of at least 10 days. Local agents can guide you through term life whole life and universal life options tailored to your needs.

Frequently Asked Questions

What license does a life insurance agent need in Massachusetts?

Agents must hold a valid Massachusetts life insurance producer license. They must complete prelicensing education and pass the state exam. Continuing education is required every two years to maintain the license.

How long is the free look period for life insurance in Massachusetts?

Massachusetts law provides a minimum 10 day free look period after you receive your policy. During this time you can cancel for any reason and receive a full refund of any premiums paid.

Can a life insurance agent in Winchester help with estate planning?

Yes many agents work with estate planning attorneys to coordinate life insurance with wills and trusts. Life insurance proceeds in Massachusetts are generally not subject to probate if a beneficiary is named.

Life Insurance Agents in Other Massachusetts Cities

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