REFERENDUM ON THE REPLACEMENT OF THE ROOF AT PEARSON SCHOOL
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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.

Camp Counselor
Due Date:
April 6, 2026
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description
 Recreation is hiring for summer positions

 Summer Camp Counselors & CITs
 
Great opportunity to gain experience, spend time outdoors, and make a difference this summer!
Applications due by April 6, 2026
Apply online or at Town Hall
Check out the flyers for full details!
Lifeguard Postion
Due Date:
April 6, 2026
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description
 Recreation is hiring for summer positions
Lifeguards
 
Great opportunity to gain experience, spend time outdoors, and make a difference this summer!
Applications due by April 6, 2026
Apply online or at Town Hall
Check out the flyers for full details!
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:
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