Maintenance Service Worker $30,000 jobs in Milton, ON

About the Role

A private family office is seeking an experienced, reliable, and discreet Property Manager & Maintenance Technician to oversee the day-to-day upkeep, maintenance planning, and property management support for a private residential property portfolio in the Greater Toronto Area.

This is a hands-on role combining general handyman work, landscaping, preventative maintenance, contractor supervision, and property management, with the flexibility to take on additional tasks as necessary. The ideal candidate is a skilled all-rounder who takes pride in maintaining properties to a consistently high standard, can work independently with minimal oversight, and is comfortable creating maintenance plans, tracking records, managing budgets, and liaising with established vendors and contractors selected by the family office.

Key Responsibilities

• Create, implement, and actively manage the maintenance plan for the residential property portfolio, ensuring routine, preventative, seasonal, and on-demand maintenance is properly scheduled, tracked, completed, and followed up on.
• Conduct regular property walkthroughs and inspections to proactively identify maintenance issues, safety concerns, deficiencies, and upcoming repair needs.
• Perform general hands-on maintenance and minor repairs, including basic carpentry, painting, lighting, minor plumbing, and overall property upkeep.
• Carry out and/or oversee seasonal exterior upkeep, including landscaping, lawn care, garden maintenance, snow removal, leaf clearing, and related grounds work.
• Respond promptly to maintenance requests and urgent property issues as they arise.
• Be available on-call outside regular business hours, including evenings and weekends when required for urgent or time-sensitive property matters.
• Coordinate, schedule, and supervise the family office’s approved vendors, trades, contractors, and outsourced service providers.
• Ensure vendor and contractor work is completed to the required standard, properly followed up on, and documented.
• Maintain accurate property management records, including maintenance logs, inspection reports, vendor visits, warranties, outstanding deficiencies, and recurring or ongoing issues.
• Manage and maintain tools, equipment, and supplies needed for the role
• Exercise sound judgment and discretion at all times when working on or around private residences
• Maintain strict confidentiality with respect to all information pertaining to the family office, its principals, property details, schedules, security measures, and any related parties

Requirements

• Minimum 5 years of relevant experience in property maintenance, handyman services, landscaping, or a related field
• Strong general handyman skill set (basic carpentry, painting, minor repairs, etc.)
• Landscaping and grounds maintenance experience
• Demonstrated ability to manage multiple properties and competing priorities
• Comfortable coordinating with and overseeing third-party vendors and contractors
• Valid driver’s license and reliable vehicle; willingness to travel to and work in downtown Toronto on a regular and on-demand basis
• Based locally in or near Oakville and/or Mississauga, for quick response times
• High degree of discretion, professionalism, and trustworthiness, as this role requires regular access to private residences
• Strong communication skills and responsiveness
• Ability and willingness to work flexible hours, including evenings and weekends as required, particularly during peak seasons, events, and other time-sensitive property needs.

Nice to Have

• Experience working with high-net-worth households, family offices, or estate management
• Basic knowledge of home systems (HVAC, plumbing, electrical) with an ability to triage issues before escalating to specialists
• Existing network of reputable trades contacts

Working Arrangement

• This is an on-demand, priority-based role. The role requires flexibility, responsiveness, and the ability to attend properties within the Greater Toronto Area as needed, including for urgent or time-sensitive matters.

Compensation & Benefits

• Compensation, including Health & Dental Benefits, will be competitive and based on experience, availability, and scope of responsibilities.
• A monthly vehicle allowance will be provided to support work-related travel between properties within the Greater Toronto Area.

To apply, please submit your resume along with 2-3 references demonstrating relevant experience.

Pay: From $85,000.00 per year

Benefits:

• Casual dress
• Dental care
• Extended health care
• Flexible schedule
• Life insurance
• Mileage reimbursement

Application question(s):

• Where are you located?
• Do you have a minimum of 5 years of experience in property maintenance, handyman services, landscaping, or a related field? (Yes/No)
• Are you willing and able to travel to and work in downtown Toronto on a regular and on-demand basis? (Yes/No)
• Are you available for, and comfortable with, on-call work outside regular business hours, including evenings and weekends, when required? (Yes/No)
• How many years of experience do you have coordinating or supervising third-party vendors and contractors? (Numeric)
• Are you comfortable providing 2–3 professional references who can speak to your relevant experience? (Yes/No)
• What is your salary expectation for this full-time role?
• What is your earliest available start date?

Licence/Certification:

• Driver's License & Reliable Personal Vehicle (required)

Work Location: In person