Job Description

Private multi-generational family seeks an experienced, dedicated long-term Domestic Couple to oversee the full-service care and year-round maintenance of four private residences on Islesboro Island, located off the coast of Maine. This is a full-time, live-in role with on-island private accommodation provided year-round. This is an ideal role for a service-oriented couple seeking to steward and manage a legacy family estate with pride, confidentiality, and commitment.

The couple will be responsible for the comprehensive interior and exterior care and oversight of the properties, supporting a high level of cleanliness, preparedness, and operational excellence throughout the year, with peak activity during the summer season (July–September). This position is suited to a couple who are hands-on, detail-oriented, and committed to long-term estate care.

Must be a reliable and personable team who take pride in their work and are eager to build a lasting, professional relationship grounded in trust, consistency, and high standards. The outgoing caretakers have been with the family for 50 years, and the family is seeking a similarly dedicated team to uphold the tradition of long-term estate stewardship.

Responsibilities include, but are not limited to:

Interior/Housekeeping:

• Daily housekeeping, deep seasonal cleans, and organization of all residences
• Laundry, ironing, and wardrobe care for multiple family members
• Inventory management and supply ordering
• Grocery shopping and home provisioning in preparation for summer season
• Occasional light meal prep and support with guest readiness
• Seasonal opening and closing of homes, including linen, furnishings, and kitchenware management
• Coordinating and overseeing 3–4 seasonal housekeepers sourced locally during summer months

Exterior/Groundskeeping:

• Year-round general maintenance and property inspections across four seasonal homes
• Light carpentry, painting, and basic repair work as needed
• Landscaping oversight including mowing, trimming, debris clearing, and firewood management
• Dock area oversight and light support with boats (full-time captain in place)
• Upkeep of vintage vehicles and seasonal recreational equipment
• Oversight of vendors, service professionals, and local contractors
• Ensure snow removal and storm preparation during off-season
• Monthly reporting and tracking of hours worked per property to family office

Requirements:

• Strong command of the English language; superb communication skills, both written and verbal
• Minimum 5-7 years’ experience working in a similar role as a couple for a private family or estate
• Excellent references required from both current and previous employers
• Experience in both interior household management and exterior/grounds maintenance
• Experience with coastal or island property management a strong plus
• Willingness to live year-round in a remote, close-knit island community
• Flexibility and adaptability in a seasonal, family-oriented environment
• Discreet, proactive, and able to work autonomously with limited supervision
• Service-minded with warm and professional demeanor
• Self-starters who take initiative and pride in their work
• Comfortable managing logistics during peak occupancy, including family gatherings and events
• Strong communication skills and ability to coordinate with remote family office
• Technologically savvy; able to manage property systems, schedules, and communications
• Valid U.S. driver’s licenses and clean driving records
• Legally able to work in the United States

Salary: $160,000 - $180,000 per annum

Benefits: Private accommodations and vehicle provided. Benefits stipend may be discussed as part of compensation package, 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

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