Job Description

Private multi-generational family seeks a skilled and self-motivated year-round, Live-In Caretaker/Property Manager 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

Benefits: Private accommodations. Performance-based annual bonus potential. Benefits stipend may be discussed for the right candidates.

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

Job Tags

Similar Jobs