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.

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