The town of Winchester/city of Winsted, Connecticut is seeking an experienced, collaborative, engaging, and enthusiastic professional to serve as Town Manager and Chief Executive Officer for Winchester. The community has had an established Town Manager/Mayor/Selectboard form of government since 1962. The town is the second largest community in Litchfield County with a population of 10,200 encompassing 33.8 square miles of land with numerous recreational opportunities mainly around the very large, desirable, and picturesque Highland Lake. The town center in Winsted is at the crossroads of Route 44 and Route 8 and has a well-defined downtown that supports many businesses in this corridor. The town has a highly respected local school system and is home to Northwestern Community College.

The recently approved budget for FY24 is $39.1 million with approximately $24 million of that total to support the local school district. The town has also approved an allocation of $2 million from the general fund to pay for capital improvements. In 2023, the S&P bond rating agency upgraded the town to AA rating for future debt service obligations. There are a total of 60 FTE’s and numerous part-time staff.

Offering a competitive salary, currently budgeted at $130,000-$150,000, and a benefits package. The starting salary level being dependent on experience, education, and qualifications. Benefits include an offering of health insurance (including dental and vision), life insurance, generous employer-matching contributions to a defined contribution plan, 14 paid holidays, sick and vacation leave accruals, paid ICMA and CTCMA membership fees, and more. The ideal candidate will have a bachelor’s degree, MPA or MBA preferred, and five years of demonstrated, progressive management experience in public administration or relevant fields. The town of Winchester is an equal opportunity employer and is actively searching for a diverse candidate pool.


To apply submit a resume and cover letter, in confidence, as a PDF to by Dec. 4.