Job Title: Property Caretaker

Reports to: Property Director

FLSA Exemption Status: Non-exempt

Position Type: Regular, Full-Time

Regular Work Hours: 40 hrs/week, year-round, M–F 7:30–4:30. Occasional evening or weekend flexibility for events/on call

Location: Cold Spring 

Last Updated: 10/1/2026

Summary: The Property Caretaker will manage the maintenance and upkeep of multiple properties on the farm, some of which host events and overnight guests. This is a hand-on position that is responsible for carpentry, painting and repair work while also overseeing a preventative maintenance program. This role requires someone who can juggle multiple projects, think ahead to anticipate maintenance needs, and work efficiently both independently and as part of a team.

Essential Areas of Responsibility 

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Site Rental and Facilities (approx. 15+ hours/week)

Perform routine maintenance, including basic plumbing, electrical repairs, carpentry and painting.

Manage and execute a preventative maintenance schedule to ensure property longevity.

Respond promptly to maintenance requests from event staff and overnight guests.

Oversee property cleanliness, organization, and overall upkeep.

Collaborate with event teams to ensure facilities are prepared for guests.

Work with vendors and contractors when specialized maintenance is required.

Maintain records of maintenance activities and supply inventory. Communicate material and equipment needs for maintenance and repair

Identify and recommend property improvements for efficiency and guest experience.

Become familiar with buildings, including alarm systems, mechanicals, and routine service/inspections

Experience with G-suite

Property-Wide Building Care

Carpentry and painting across all campus buildings and residences (interior and exterior repair, trim, doors, siding, finish work).

Take a task list or small project from start to finish with periodic check-ins, not daily direction.

Help track completed, deferred, and upcoming seasonal building work.

Serve as a technical backstop for the Site Coordinators on repairs outside their usual scope. No supervisory authority.

Help scope and coordinate subcontractor work when a job needs outside help.

Year-round coverage, including winter and shoulder-season building work.

Qualifications & Skills

Demonstrated carpentry and painting skill well beyond basic (photos or examples of your work expected), plus working knowledge of basic plumbing and electrical.

Track record of completing assigned work independently, without close supervision

Ability to prioritize tasks and manage multiple projects simultaneously.

Strong problem-solving skills and a proactive mindset.

Comfortable working independently and within a team setting.

Physical ability to perform manual labor, including lifting, climbing, and standing for extended periods.

Strong attention to detail and ability to anticipate maintenance needs.

Versatility: comfortable moving between trades and task types in a single week.

Personable, professional manner with guests, event staff, and colleagues across departments.

Valid driver's license and reliable transportation to Cold Spring. (license is repeated below)

Preferred Qualifications

Previous experience maintaining event or hospitality spaces.

Experience with older or historic buildings

Familiarity with HVAC systems and general handyman skills.

Basic knowledge of safety and compliance regulations for building maintenance.

Administrative Responsibility

Submit weekly timesheets to supervisor according to current requirements

Attend trainings in administrative procedures as required

Attend safety trainings as required\

Work Environment: This job is performed both indoors and outdoors with occasional administrative work.

Physical Demands: This is a physically active role. The Property Caretaker must be willing and able to:

Lift and move materials, up to 50 pounds at a time

Operate power tools

Perform other physical activities as needed for building equipment and maintenance

Work steadily outdoors in heat, cold, rain, and wind. (Working outdoors is not required when conditions are hazardous to human health.)

Additional Eligibility Qualifications

Affinity for Glynwood’s mission

Valid US driver license in good standing

Provable eligibility to work in USA

Other Duties: Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee for this job. Duties, responsibilities and activities may change at any time with or without notice.

If you have any photos of your carpentry or painting work please attach photos.