Caretaker Live In, Live Out, Property Manager

A family on Shelter Island needs to hire a hands‑on Property Manager to oversee the year‑round maintenance, operation, and presentation of their waterfront estate, consisting of a main house, guest houses, waterfront facilities, and supporting infrastructure.

• Maintain the residence in excellent condition at all times with the help of a housekeeper.
• Oversee the daily operation and maintenance of all buildings, grounds, and waterfront facilities.
• Understand and supervise pool equipment, heaters, and the pool company.
• Service family‑owned vehicles.
• Conduct regular inspections and address issues proactively.
• Ensure the estate is always guest‑ready and professionally presented.
• Maintain and oversee dock facilities; coordinate care and operation of motor boats and small watercraft.
• Manage seasonal preparations, inspections, servicing, and vendor relationships related to marine equipment.
• Follow off‑season maintenance schedules for septic systems, HVAC, electrical, plumbing, water, and security systems.
• Serve as the primary point of contact for vendors, service personnel, outside contractors, and service providers.
• Maintain a clay tennis court to professional standards.
• Monitor and maintain all security systems.
• Possess strong knowledge and ability to troubleshoot WIFI, smart home, and AV systems.
• Perform routine repairs and maintenance tasks; troubleshoot property systems and coordinate specialized repairs when required.

• Minimum 5+ years of experience managing private estates, luxury residences, resorts, yachts, or similar properties.
• Strong knowledge of residential mechanical systems, WIFI, Smart home, HVAC, plumbing, electrical, and preventative maintenance programs.
• Experience supervising household staff and outside vendors.
• Ability to perform hands‑on repairs and maintenance.
• Experience with waterfront properties and boats preferred.
• Self‑motivated professional who takes ownership of every aspect of estate operations, balancing vendor and staff management with personal maintenance duties.

Schedule:

6 days during the summer and 5 days the rest of the year.

Salary range: $150,000+ annually. Employer‑provided housing for the right candidate.

Comprehensive medical coverage and dental insurance. September start.