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Carefree Hosting is a growing short-term rental management company overseeing 20+ properties throughout the region. As our portfolio expands, we are transitioning from reactive maintenance coordination to a structured, preventative maintenance system.

We are seeking a highly organized, mechanically skilled Maintenance Manager to oversee maintenance operations across our portfolio.

This is a leadership-level, responsibility-based role — not just a handyman position.

Position Overview

The Maintenance Manager will oversee property maintenance operations across multiple short-term rental properties, ensuring homes remain safe, compliant, guest-ready, and proactively maintained.

This position starts as part-time (approximately 20–25 hours per week) with flexible scheduling requirements. As the portfolio grows to 28–30+ properties, the role is expected to transition into full-time.

This is not a traditional 9–5 position. The right candidate must be comfortable with flexibility and occasional urgent response needs.

Responsibilities

  • Develop and manage preventative maintenance schedules for each property
  • Coordinate HVAC, septic, plumbing, electrical, propane, and seasonal services
  • Oversee and prioritize handyman tasks
  • Schedule and supervise outside contractors
  • Prepare properties for inspections and ensure safety compliance
  • Develop storm and winter preparedness plans
  • Conduct periodic property condition checks
  • Coordinate emergency repair response
  • Support capital improvement projects
  • Maintain organized maintenance documentation and property profiles

Qualifications

  • Strong working knowledge of residential systems (HVAC, plumbing, electrical basics)
  • Mechanically inclined with troubleshooting ability
  • Highly organized and systems-oriented
  • Comfortable managing multiple properties simultaneously
  • Confident decision-maker
  • Professional communication skills
  • Ability to manage contractors and ensure quality work
  • Valid driver’s license and reliable transportation

Preferred:

  • Experience in property management or facilities oversight
  • Skilled trade background
  • Project management experience
  • Experience preparing properties for inspections

Work Structure

  • Part-time (20–25 hours per week to start)
  • Flexible schedule based on operational needs
  • On-site presence required for inspections, vendor oversight, and projects
  • Availability for urgent issues when necessary
  • Opportunity for growth into full-time leadership role as portfolio expands

Why Join Carefree Hosting?

  • Growing and forward-thinking company
  • Opportunity to build and structure a maintenance department
  • Leadership-level role with room for expansion
  • Direct impact on operational standards and company growth

To apply, please submit your resume and a brief description of your experience managing resident

Pay: $35.00 - $40.00 per hour

Work Location: Hybrid remote in Oneonta, NY 13820

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