Live-In Property Manager / Caretaker Job at Hire Society, Islesboro, ME

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  • Hire Society
  • Islesboro, ME

Job Description

Private multi-generational family seeks a skilled and self-motivated year-round, Live-In Property Manager / Caretaker to oversee the exterior and interior maintenance and mechanical upkeep of four seasonal residences located across the island. This is a full-time, year-round, live-in role with on-island private accommodation provided, year-round, for a dedicated individual who takes pride in the care of a rural coastal property and is looking for a long-term placement in a trusted position. The outgoing caretaker has served the property for over 50 years, and the family seeks a professional who will uphold the tradition of long-term estate stewardship with integrity, discretion, and hands-on commitment.

Responsibilities include, but are not limited to:

  • Year-round property inspections and general exterior maintenance across four family homes
  • Routine upkeep of mechanical systems (HVAC, plumbing, appliances) in collaboration with service providers
  • Basic carpentry, painting, and small-scale repair work
  • Landscaping and groundskeeping: mowing, trimming, storm cleanup, snow removal
  • Firewood chopping and stacking; clearing paths and debris
  • Seasonal property preparation: opening homes in June, closing in September
  • Vehicle care, including routine cleaning, fueling, and coordination of maintenance
  • Support with dock area and small boat upkeep (full-time captain in place)
  • Oversight of outside vendors, tradespeople, and seasonal contractors
  • Regular communication and reporting to remote family office, including monthly work summaries

Requirements:

  • Strong command of the English language; excellent communication skills
  • Minimum 5-7 years’ experience in a similar role for a private estate or family
  • Excellent references required from current and previous employers
  • Experience with year-round exterior maintenance and hands-on property care
  • Discreet, proactive, and highly dependable with an “all-in” mindset
  • Comfortable working independently in a remote island environment
  • Technologically savvy; capable of overseeing systems, contractors, and seasonal needs
  • Hands-on, hard-working, and solutions-oriented
  • Experienced in maintaining coastal or remote properties
  • Comfortable with seasonal demands and light summer oversight of support staff
  • Able to take initiative while following family office directives
  • Loyal, discreet, and service-focused with a strong work ethic
  • Physically capable and confident managing diverse property systems
  • Valid U.S. driver’s license with clean driving record
  • Legally able to work in the United States

All salaries are dependent on experience and references, and all candidates must be willing to submit themselves for a Federal Background Check

Benefits: Private accommodations. Performance-based annual bonus potential.

Benefits stipend may be discussed for the right candidates.

Job Tags

Full time, For contractors, Summer work, Seasonal work, Remote job,

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