The Town of Winchester offers the following benefits:

HEALTH INSURANCE (Effective date of hire or 7/1 annual open enrollment date – refer to rate sheet for current cost – plan summaries are available upon request)*

Plan Options:  

DELTA DENTAL INSURANCE (Effective date of hire or 7/1 annual open enrollment date – refer to rate sheet for current cost – plan summaries are available upon request)*  


 Health and Dental Rates 7.1.2023 - 6.30.2024                                                                                                                 

Please be advised that insurance premiums, for all plans, are deducted 
one month in advance of coverage.

BASIC $4,000. TERM LIFE and AD & D INSURANCE (Current cost is .76 cents per week) *

OPTIONAL LIFE, SHORT TERM DISABILITY INSURANCE, & ACCIDENT INSURANCE (Description sheet available with benefits and cost) *


FLEXIBLE SPENDING REIMBURSEMENT PLANS (MEDICAL EXPENSE & DEPENDENT CARE EXPENSE) * These plans provide employees with the opportunity to pay for certain out-of-pocket medical expenses and dependent care expenses on a pre-tax basis.

EMPLOYEE ASSISTANCE PROGRAM (EAP) – A confidential counseling and referral service available to employees, their household members and dependents.  The EAP provides assistance with legal matters, financial consultation, and counseling for a wide range of personal concerns, including drug & alcohol abuse, stress, depression, or other emotional issues. 


DIRECT DEPOSIT OF PAYROLL FUNDS - Please contact Human Resources at (781) 721-7157 or 

WINCHESTER FEDERAL CREDIT UNION - Located at 63 Shore Road, Unit 11, Winchester, MA (781-729-0668).  Information on available financial services, including direct deposit to a credit union account, may be obtained at that location.   

PENSION PLAN – Those eligible for participation in a pension plan will be required to enroll with either the Town of Winchester Retirement Office or the Massachusetts Teachers’ Retirement System.  All others will be required to enroll in the Town’s mandatory 457 Deferred Compensation Plan administered by ICMA Corporation (this plan is used in lieu of Social Security - information on this plan is available through the Treasurer’s Office).

TAX DEFERRED COMPENSATION PLAN (Voluntary) – In addition to the pension plan, Town employees may voluntarily contribute funds to a tax deferred compensation plan (457) through ICMA Corp.  Information on plan participation may be obtained from the Treasurer’s Office.   School employees may elect to voluntarily contribute to a tax sheltered 403B plan established pursuant to M.G.L., Chapter 71, Section 37B.  Information for School employees may be obtained from the School Business Office, Central Office.

*Newly hired employees must submit all insurance enrollment forms to the Human Resources Office within ten days of their hire date.