Job Listing: 18693

Position: Caretaker, Full Time, Property Manager
Location: Live-in, Live-out, Long Island, New York, Suffolk County

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. The property consists of a main house and guest houses, waterfront facilities, and supporting infrastructure requiring proactive management and exceptional attention to detail. Responsibilities include: maintaining residence in excellent condition at all times with the help of a housekeeper, overseeing the daily operation and maintenance of all buildings, grounds, waterfront facilities, understanding of pool equipment/heaters/supervising the pool company, servicing family-owned vehicles, conducting regular inspections and address issues before they become problems, ensuring the estate is always guest-ready and professionally presented, maintaining and overseeing dock facilities, coordinating the care and operation of motor boats and small watercraft, managing seasonal preparations, inspections, servicing, and vendor relationships related to marine equipment. Follow established off season maintenance schedules and service logs for – Septic systems and pumping schedules, HVAC equipment, Electrical systems, Plumbing systems, Water systems and Security systems, serving as the primary point of contact for vendors and service personnel, overseeing outside contractors and service providers, maintaining a clay tennis court to professional standards, monitoring and maintaining all security systems. Strong knowledge and ability to troubleshoot problems with WIFI networks, smart homes and AV systems is a must. Hands-On maintenance duties include: performing routine repairs and maintenance tasks whenever practical, troubleshooting property systems and coordinating specialized repairs when required. All candidates must balance managerial responsibilities with active participation in maintaining the estate. Qualifications: 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. The ideal candidate is a self-motivated professional who takes ownership of every aspect of estate operations. This individual must be equally comfortable managing vendors and staff, maintaining detailed service schedules, and personally handling repairs and maintenance to ensure the property remains in exceptional condition throughout the year. Schedule: 6 days during the summer and 5 days for the rest of the year. Salary range: $150k + annually. Employer-provided housing for the right candidate. Comprehensive medical coverage and dental insurance. September start.

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