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 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
• Landscaping tasks 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
• 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

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.