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Senior Maintenance Supervisor (Village at Brookline)

$79k to $98k

Boston, MA, United StatesLeadPosted Nov 3, 2026

Against the Boston typical range

Job description

At Winn. Companies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 30 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed-income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact. Interested in learning more?

Visit Winn. Companies to explore our benefits , mission, communities, and career opportunities. About the Opportunity Winn. Companies is searching for a Senior Maintenance Supervisor to join our team at Village at Brookline , a 193-unit affordable housing community located in Brookline, MA; The Residences at Brighton Marine, a 102-unit affordable housing community; and Oliver Lofts II, a 19-unit affordable housing community, where both properties are located in Boston, MA .

In this role, you will oversee maintenance operations across multiple properties while performing hands-on maintenance functions as a working supervisor. You will lead maintenance teams and help ensure the physical condition, safety, appearance, and overall maintenance of the properties meet ownership, management, and Winn standards.

The pay range for this role is $38.00-$47.00 per hour. The selected candidate will adhere to the following schedule: Monday through Friday from 8:00AM to 5:00PM with the ability to work on-call duty for emergencies.

Responsibilities

Lead and manage maintenance staff across assigned properties while serving as a hands-on working supervisor as needed. Assist with hiring, training, developing, and holding maintenance staff accountable to operating standards, and participate in weekly staff meetings. Prepare maintenance staff and vendor schedules to complete service requests, preventive maintenance, unit upkeep, and curb appeal requirements.

Conduct monthly building inspections, review third-party property inspections, and coordinate necessary maintenance repairs. Maintain working knowledge of maintenance programs and capital improvement projects, and assist Property Managers in controlling maintenance expenses. Solicit contractor bids with approval from the Property Manager and Regional Maintenance Manager.

Participate in on-call and emergency maintenance during off-hours and perform hands-on maintenance activities as needed.

Requirements

High school diploma or GED equivalent. 5-8 years of experience in apartment, property, facilities, or building maintenance. 5+ years of supervisory and management experience. General knowledge of electrical, plumbing, appliance, and HVAC maintenance. Current driver's license in good standing and ability to meet the driving record standards outlined in the Company Safe Vehicular Operations Policy.

Previous experience with REAC / NSPIRE inspections. Previous experience with capital improvement projects. EPA certification. HVAC certification. Basic computer skills with the ability to navigate web-based applications. Strong customer service, verbal and written communication skills, with the ability to work effectively with diverse groups of people and personalities.

Strong supervisory and leadership skills. Availability for on-call activity during off-hours to address urgent maintenance needs.

Preferred Qualifications

Vocational or technical training. Certified Apartment Maintenance Technician (CAMT) and Heating, Ventilation, and Air Conditioning (HVAC) certifications. Previous experience with property management software.

Benefits

& Perks Eligible full-time U.S. employees enjoy a competitive benefits package, including: Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options 401(k) with company match and company-paid life, AD&D, and long-term disability insurance Tuition reimbursement, professional development opportunities, and career growth resources Wellness programs, employee assistance resources, commuter benefits , and employee discount programs Flexible work options for eligible positions Learn more about our benefits at https://www.

winnbenefits.com . If you are a California Resident, please see our Notice of Collection here . It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors. Internal candidates, please apply here: Internal Careers Hub

Description copied from Winn's careers page. Read the full posting before you apply.

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