2026 Leaf Pickup Schedule – November 30th – December 3rd, 2026
Read More

Job Openings

Below is a list of positions for which we are currently accepting applications. In order to be considered for employment with the Town, you must fully complete the Town’s application form and return it, along with a Resume and Cover Letter, by email or by mail, unless otherwise specified in the Job Announcement. Click here to see the Town’s application form.

We accept applications via email. Applications can be emailed to thall@townofwinchester.org or mailed to us at Attn: Town Manager’s Office, Winchester Town Hall, 338 Main Street, Winsted, CT 06098. Please note that we only accept applications for employment when a position has been posted; we do not maintain general interest resumes.

Senior Center Director
Due Date:
November 30, 2026
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description
SENIOR CENTER DIRECTOR
$34.19 - $44.18 hourly 
Town of Winchester
The Town of Winchester is seeking qualified applicants for a full-time Senior Center Director position.
Job Description & Application:
The complete job description and employment application are available online at:
Applications may also be obtained from the Town Manager’s Office, Town Hall, 338 Main Street, Winsted, CT 06098.
How to Apply:
Interested candidates should submit a completed employment application and resume by one of the following methods:
Please include “Senior Center Director” in the subject line.
Mail:
Town of Winchester
 Town Manager’s Office
 338 Main Street
 Winsted, CT 06098
Please clearly mark “Senior Center Director” on the front of the envelope.
EEO/AA/M/F/D/V
We encourage qualified candidates to apply!
 
 
P/T Finance/Human Resources
Due Date:
November 13, 2026
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Part-time
Job Description
Winchester Housing Authority
 POSITION: P/T Finance/Human Resources 
 
This position is: Part-Time (18 Hours) Monday – Wednesday 8:00am – 2:30pm 
Salary Range: $29-$32 
 
PURPOSE: 
Under the general supervision of the Executive Director, Direct financial activities of the Winchester Housing Authority to assure accurate financial records are maintained in compliance with Federal, State, City and Winchester Housing Authority requirements. The position is responsible for all operation records, banking accounts, accounts payable, payroll and investment information. Creating and maintaining all general ledgers and producing related accounting and management reports. Responsible for the front window. Answer and Return calls/messages. Prepare financial statements and all other required or requested reports for all State and Federal programs. Assist the Executive Director in the daily operation of the Housing Authority.

PLEASE SEND YOUR RESUME TO:

            WINCHESTER HOUSING AUTHORITY

            80 CHESTNUT STREET

            WINSTED, CT 06098

            ATTENTION: EXECUTIVE DIRECTOR

NO CALLS PLEASE

Maintainer III
Due Date:
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description
JOB OPENING
TOWN OF WINCHESTER, CT
Highway Maintainer III
$26.10 - $30.77hr
 
The Town of Winchester has an opening for a Highway Maintainer III at the Department of Public Works.  Complete job description and application available from the office of the Town Manager, Town Hall, 338 Main Street, Winsted, CT 06098 
 Please send resume, and completed application by email to thall@townofwinchester.org with “ Maintainer III” in the subject line or by mail to Town Manager’s Office , 338 Main Street, Winsted, CT 06098 with  “ Maintainer III” clearly marked on the front of the envelope.  EEO/AA/M/F/D/V
 
Police Officer
Due Date:
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description

 The Town of Winchester is accepting applications for entry level police officers to fill full time positions. Candidates must be 21 years of age and possess a valid Connecticut Driver License and a high school diploma or equivalent.  All candidates must pass the CPCA Written exam prior to submitting a completed application to the Town of Winchester and will be required to successfully complete written and oral examinations, physical wellness exam including drug screening, background investigation, polygraph examination, psychological examination, and Police Chief’s interview. Entry level candidates must provide proof of passing the CHIP Physical Abilities Assessment prior to the written test being given. The salary range is $84,872.83-$89,410.97.  Deadline for application is.  To submit an application or view a more complete job announcement go to www.PoliceApp.com/WinchesterCT
The Town of Winchester is an Equal Opportunity/Affirmative Action Employer.
 
Part Time School Crossing Guard
Due Date:
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Part-time
Job Description
PART TIME ALTERNATE SCHOOL CROSSING GUARD
TOWN OF WINCHESTER, CT
Salary $16.35/hr.  
 
The Town of Winchester, CT is seeking candidates to be considered for part time School Crossing Guard for the Winsted Police Department.  Job description and application available from the Town Manager's office, Town Hall, 338 Main Street, Winsted, CT 06098 or at https://www.townofwinchester.org/job-openings
Completed applications can be dropped off at the Police Department, 338 Main Street, Winsted, CT 06098 open until filled.  EEO/AA/M/F/D/V