Property Caretaker
Listed on 2026-09-22
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Maintenance/Cleaning
Groundskeeper, Maintenance Technician / Mechanic, Building Maintenance, Lawn Care
Property Caretaker – Cape Cod, MA
An accomplished executive couple with grown children is seeking an experienced, hands-on Property Caretaker to take over the day-to-day care of their beautiful Cape Cod estate from a long-term caretaker who is retiring after ten years.
This is a full-time, year-round, live-in position with a significant focus on landscaping, grounds maintenance, and general property care. The property is already exceptionally well maintained, and the successful candidate will take ownership of keeping it that way.
The ideal candidate takes pride in maintaining beautiful grounds and a well-cared-for home and is equally comfortable mowing a lawn, maintaining beds and shrubbery, servicing equipment, handling a minor repair, or coordinating an outside contractor. Strong landscaping knowledge, practical maintenance skills, and familiarity with mowers, small motors, and grounds equipment are important.
This individual must be proactive and observant, identifying potential issues before they become problems. When the principals are in residence, the Property Caretaker should be attentive and available while maintaining a discreet and unobtrusive presence.
A separate private residence with utilities included is provided onsite and may be furnished or unfurnished.
Responsibilities- Hands-on care of the expansive grounds, including mowing, weeding, mulching, maintaining beds, trimming hedges and shrubbery, and seasonal cleanup
- Regular inspection and care of the residences, grounds, garages, and property systems
- Perform routine preventative maintenance, handyman work, and minor repairs
- Maintain and service mowers, landscaping equipment, small motors, tools, and other property equipment
- Proactively identify maintenance needs and property deficiencies
- Coordinate and oversee established vendors and contractors and source new providers as needed
- Coordinate specialized services including HVAC, plumbing, electrical, pool, and other property maintenance
- Oversee seasonal opening, winterization, storm preparation, and cleanup
- Monitor property security and alarm systems and respond to issues as needed
- Coordinate with the third-party housekeeping team as needed
- Assist with occasional property-related purchasing, deliveries, vehicle needs, and household setup
- Maintain property records, service schedules, warranties, and related documentation
- Report property deficiencies and emergencies promptly to the Estate Manager
- Maintain a professional and discreet presence when the principals are in residence
- Minimum five years of relevant private estate, high-end residential, grounds, or comparable experience
- Significant hands-on landscaping and grounds maintenance experience required
- Strong knowledge of lawn care, plantings, beds, hedges, shrubbery, and seasonal maintenance
- Experience with mowers, small motors, landscaping equipment, and tools
- Strong handyman and practical property maintenance skills
- Working knowledge of irrigation, HVAC, plumbing, electrical and mechanical systems, and winterization
- Experience with seasonal or oceanfront properties strongly preferred
- Comfortable managing and evaluating vendors and contractors
- Proactive, observant, organized, and able to work independently
- Dependable, responsive, trustworthy, and discreet
- Professional, approachable, collaborative, and even-tempered
- Valid driver's license and clean driving record required
- Seeking a long-term position
- Willing to reside onsite year-round
This is a full-time, year-round position. April through October is the busiest period due to the seasonal demands of the property and grounds. Winter months are typically lighter and focus on property oversight, storm preparedness, seasonal maintenance, and equipment care.
Flexibility is required during peak season, owner visits, holidays, severe weather, and property emergencies.
Compensation is $120,000–$130,000 annually, commensurate with experience, plus benefits.
A separate private residence with utilities included is provided onsite and may be furnished or unfurnished.
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