Full-Time Handyman | Houseman

A private family is seeking a full-time Handyman | Houseman to join their long-standing property team on Cape Cod, supporting a compound of three separate homes on a 10-acre waterfront property. This is a hands-on, general trades role covering groundskeeping, light maintenance, painting, carpentry, simple plumbing, and daily upkeep across the property, working closely under the direction of the family's trusted, long-term Property Manager.

There is meaningful room for growth in this role over time as the candidate builds trust and expertise within the property team. The family is looking for someone with real trade skills and a strong work ethic who can continue developing professionally, not someone brand new to the field, but genuine long-term potential is very much part of this opportunity.

The property sees regular use June through September, with the family in residence and frequent guests, events, and entertaining. From roughly September through May, the family is present only occasionally (a few nights per month), and the off-season is largely governed by ongoing construction and improvement projects.

Daily Property Upkeep

• →Groundskeeping support, including tidying outdoor spaces, cleaning bugs and cobwebs from windows and exteriors, and power washing as needed
• →Take out trash, break down boxes, and manage general property cleanliness
• →Conduct regular walkthroughs of the property, inside and out, proactively identifying and addressing anything that needs attention
• →Check that all systems are functioning properly (lighting, Wi-Fi, TVs, appliances) and flag or resolve issues as they arise

General Trades & Light Maintenance

• →Perform light painting, carpentry, and simple plumbing repairs
• →Apply general trades knowledge to address a wide range of everyday maintenance needs
• →Maintain and inspect vehicles on the property, including basic upkeep, cleaning, and coordinating inspections
• →Keep tool sheds, attic storage, and equipment fully stocked and well organized

Events & Seasonal Support

• →Support setup and breakdown for outdoor events and hosting during the busy summer season, including arranging outdoor furniture and tables
• →Provide consistent, all-hands-on-deck coverage during peak summer months, including weekends
• →Assist with property readiness ahead of family arrivals and turnover between uses

Systems & Organization

• →Help build and maintain better property systems over time, including inventory tracking, task logs, and documentation of what's being done and where things are stored
• →Move the property from a reactive maintenance mindset to a more proactive, planned approach
• →Take initiative and self-start on identifying and completing tasks rather than waiting to be directed

Vendor & Project Support

• →Serve as an on-site presence for larger construction and improvement projects, coordinating with general contractors and specialized vendors (landscapers, plumbers, electricians, painters, carpenters) as needed
• →Handle lighter maintenance tasks directly to reduce reliance on outside vendors where appropriate
• →Communicate clearly and consistently with the property team and family regarding status, needs, and completed work

Team & Collaboration

• →Work collaboratively and respectfully alongside the property's existing long-term staff, including the Property Manager and household team
• →Be available for emergencies and urgent property needs as they arise
• →Support a smooth, low-drama working relationship with the team, understanding this is a long-established, trusted household

Full-time, with someone expected on property essentially year-round. Summer months (June-September) require more coverage given the volume of family presence, guests, and events. The off-season (September-May) is lighter but still requires regular presence and availability, particularly given ongoing construction projects and the property's exposure to coastal weather.

• A minimum of 5+ years of experience working for a professional property management company or in a similar estate/property maintenance role strongly preferred
• Well-rounded general trades skills: painting, carpentry, basic plumbing, and general handyman capability
• Physically capable of the demands of the role, including outdoor work, lifting, and active property upkeep
• Strong work ethic, high integrity, and a trustworthy, detail-oriented approach; this property includes valuables and requires someone the family can fully rely on
• Comfortable being mentored and coached by a long-term, highly experienced property manager, with a collaborative, team-first mindset
• Self-starter who takes initiative rather than waiting for direction
• Well-organized and disciplined, with an interest in helping build out better systems and processes over time
• Comfortable working around small dogs when guests are present
• Presently lives within a commutable distance of Cape Cod (02540 area) - no relocation candidates considered
• Legally authorized to work in the United States
• Reliable vehicle and valid driver's license
• Willing to be on call for property emergencies as needed
• Willing to undergo a background check and provide strong professional references