Job Description

Job Description:

Private family seeks a dedicated, hands-on, and highly communicative Property Caretaker to oversee the full-service care and year-round maintenance estate on Fishers Island, NY. This position blends operational oversight with hands-on property maintenance, vendor coordination, and general estate care. The family resides primarily in New York City and spends time at the home during the summer and early fall. The Caretaker will serve as the principal’s on-site representative and operational lead, ensuring the estate remains well-maintained, secure, and always principal and guest ready.

This is a full-time, year-round, live-out position, ideally suited to a candidate residing somewhat near the New London–Groton, CT ferry landing. The approximate schedule is Monday through Friday, 8:00am–4:00pm, with flexibility to accommodate occasional extended hours as needed.

The ideal candidate is a reliable, solutions-driven professional with a calm, service-oriented demeanor, and a strong sense of personal accountability. Exceptionally organized and proactive, they bring a “no task too small” mindset and are confident managing seasonal needs, small-scale repairs, and trusted vendor relationships . The caretaker will take pride in the property, while ensuring principals preferences and vision are executed with clear and consistent communication to keep them fully informed. A respectful understanding of home systems and an ability to self-direct are essential. A vital part of this role will be to keep the principals informed of completed tasks, active projects, and upcoming needs, while also supporting long-distance confidence in the estate’s overall readiness and care.

Responsibilities include, but are not limited to:

• Managing the daily, weekly, seasonal and annual upkeep and maintenance of the estate and grounds
• Routine household maintenance: trash/recycling management, stocking supplies, light cleaning
• Groundskeeping: mowing, trimming, field cutting, debris clearing, edging, and care around rock beds
• General upkeep of outdoor areas, including window washing, furniture cleaning, and pest control oversight
• Perform safety and functionality checks on systems: water heaters, filters, plumbing, septic, HVAC
• Gutter clearing, seasonal door/window battening for storms, and hurricane preparedness
• Seasonal dock management: spring installation and post–Labor Day removal
• Painting (interior during winter; exterior during spring and fall), light carpentry, and general repair work
• Maintenance of equipment and vehicles, including tractor, pickup truck, saws, mowers, carpentry tools, and an “island car”
• Coordinating with a trusted network of vendors and service providers (plumber, roofer, pool contractor, etc.); pool servicing remains with current vendor
• Task scheduling and documentation using household manuals and/or digital systems
• Emergency readiness: annual insurance reviews, storm prep, supply management
• Running errands and sourcing materials locally (e.g., Home Depot runs)
• Delivering weekly status updates via email to principals; maintaining a proactive, ownership-oriented approach
• Additional caretaker/property management responsibilities as requested

Requirements:

• Strong command of English language; exceptional communication skills, both written and verbal
• Excellent references required from both current and previous employers
• Minimum 5 - 7+ years managing a private property or estate
• Broad skillset in home and grounds maintenance, with comfort handling both interior and exterior responsibilities
• Proven ability to manage multiple projects, timelines, and vendor relationships
• Exceptional organizational skills and dedication to responsibilities
• proactive problem solver with an above and beyond attitude and service-oriented, team mindset
• Ability to exercise quick and accurate judgment and work well in a busy environment where the utmost discretion and confidentiality are required
• Ability to seamlessly follow direction as well as independently lead a team
• Poised, positive, and professional in both mindset and manner
• Computer savvy with proficiency in both Mac and PC systems
• Proficiency in documenting work schedules and communicating task updates concisely and with diligence
• Reliable, personable, and adaptable to seasonal shifts and evolving needs
• Flexibility in scheduling with willingness to work extended hours as needed
• Reside within 15 minutes of the New London–Groton ferry terminal and be comfortable commuting
• Possess a valid U.S. driver’s license with clean driving record and have reliable transportation
• Legally authorized to work in the United States for any employer

Compensation : Around $120,000 per annum plus benefits

All salaries are dependent on experience and references, and all candidates must be willing to submit themselves for a Federal Background Check

Job Tags

Full time, For contractors, Summer work, Seasonal work, Long distance, Live out, Shift work, Monday to Friday,

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