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 Leasing & Occupancy Coordinator -Winchester Housing Authority

Due Date:

July 15, 2026

Download Job Application Download Job Description

Job Type:

On-site

Commitment:

Part-time

Job Description

Part-Time (19 hours) Leasing & Occupancy Coordinator –Monday – Thursday 9am – 2pm.

Performs all aspects of office processes for the Winchester Housing Authority Public Housing

programs.

Send letter of interest with qualifications before July 15, 2026, to: Winchester Housing Authority
80 Chestnut Street
Winsted, CT 06098
Attention: Executive Director.

No Phone Calls Please. EOE

Part-time Maintenance I -Winchester Housing Authority

Due Date:

July 3, 2026

Download Job Application Download Job Description

Job Type:

On-site

Commitment:

Part-time

Job Description

MUST HAVE A WORKING KNOWLEDGE OF MAINTENANCE AND JANITORIAL PROCEDURES.
• MUST BE ABLE TO MAINTAIN RECORDS
• CREATE WORKORDERS ON HOUSING SOFTWARE
• READ AND SEND EMAILS
• MAINTAIN RECORDS
• USE GOOD JUDGEMENT
• WORK INDEPENDENTLY
• ABLE TO WORK WELL WITH OLDER AND HANDICAPPED/DISABLED PERSONS AND WITH THE GENERAL PUBLIC.

HOURLY PAY $22-$28

PLEASE SEND YOUR RESUME TO:
WINCHESTER HOUSING AUTHORITY
80 CHESTNUT STREET
WINSTED, CT 06098
ATTENTION: EXECUTIVE DIRECTOR

Police Officer

Due Date:

Download Job Application Download 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 Application Download 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