ANNUAL TOWN BUDGET REFERENDUM-Tuesday, May 27, 2025
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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.

Housing Authority-Executive Director
Due Date:
June 6, 2025
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description
The Housing Authority of the Town of Winchester seeks a dynamic and visionary leader to serve as its Executive Director. This pivotal role offers the exciting opportunity to shape and re-energize the future of housing within our community.
The ideal candidate will possess strong skills and experience in:


●     Strategic planning and execution
●     Financial management and budgeting
●     Public housing regulations and compliance (HUD, DECD, CHFA)
●     Communications with local municipal officials to comply with safety regulations 
●     Property management and maintenance
●     Team leadership and development
●     Communication and interpersonal skills
●     Stakeholder engagement and relationship building
●     Problem-solving and decision-making

Candidates must possess one or more of the following:


●     A bachelor’s degree in Public Administration plus demonstrated experience.
●     Five (5) years of experience as an Executive Director of a housing authority.
●     Seven (7) years of progressively responsible experience in the management of public housing, preferably at a top supervisory level in housing management, building maintenance, or a related field.
●     A combination of experience and education demonstrating proficiency in managing large organizations, work with state, local, and federal regulations, and building relationships with people

Human Resources Position
Due Date:
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description
Human Resources Position at Winchester Publis Schools
Apply online via our website at www.winchesterschools.org using Applitrack 
EXECUTIVE ASSISTANT TO THE SUPERINTENDENT
Due Date:
Download Job ApplicationDownload Job Description
Job Type:
On-site
Commitment:
Full-time
Job Description

Category: Secretarial/Clerical/Secretary
Date Posted: 5/6/2025
Location: Central Office
Date of Availability: ASAP
Date Closing: Open until filled

Executive Assistant to the Superintendent:
The Executive Assistant assists and supports the Superintendent and the school board to ensure the effective and efficient operation of the district.  The Executive Assistant is responsible for processing and maintaining the Superintendent’s confidential and non-confidential correspondence.  The Executive Assistant assists with keeping records and filing reports, ensuring absolute confidentiality of information, files, and records.
QUALIFICATIONS:  Minimum of a two-year degree in clerical/office management or five years’ experience performing, at a high level, the duties and responsibilities associated with this position.  Must possess strong organizational, problem-solving, and computer skills.

REPORTS TO: Superintendent
To Apply:
https://www.applitrack.com/winchesterschools/onlineapp/

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.
 
Board Clerks
Due Date:
Download Job ApplicationDownload Job Description
Job Type:
Remote & On-site
Commitment:
Contractor
Job Description
The Town of Winchester, CT has  openings for Board Clerks. Salary is a stipend for the production of each set of meeting minutes:
1-60 Minute Meeting: $45.00
An additional $25 is provided to the Board Clerk for each additional hour the meeting lasts thereafter.
 
Complete job description and application available from the office of the Town Manager, Town Hall, 338 Main Street, Winsted, CT 06098 or online at 
 
Applications will be accepted until filled. Applications can be emailed to Thall@townofwinchester.org  or mailed to the Town of Winchester, 338 Main Street, Winsted CT 06098 Att: Town Manager’s office.  EEO/AA/M/F/D/V
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  $15.69/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