Town of Winchester Announces Release of RFQ/RFP for Wallens Hill Residential Development Project
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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.

Part-time Maintenance I -Winchester Housing Authority
Due Date:
October 14, 2025
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Part-time
Job Description
PLEASE SEND YOUR RESUME TO: 
WINCHESTER HOUSING AUTHORITY 80 CHESTNUT STREET 
WINSTED, CT 06098 
ATTENTION: EXECUTIVE DIRECTOR 
Highway Maintainer III/Cemetery Attendant
Due Date:
October 9, 2025
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Job Type:
On-site
Commitment:
Full-time
Job Description
Highway Maintainer III/Cemetery Attendant  
$26.64 - $31.30/hr. DOE
 
The Town of Winchester has an opening for a  Maintainer III/Cemetery Attendant
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 or
Please send resume and completed application by email to thall@townofwinchester.org with “Highway Maintainer III/Cemetery Attendant” in the subject line or by mail to Town Manager’s Office , 338 Main Street, Winsted, CT 06098 with “ Highway Maintainer III/Cemetery Attendant” clearly marked on the front of the envelope.  Applications are due by 10/09/2025.  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 $55,944 to $74,362.  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:
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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