Reisdent Head Gardener / Caretaker for Historic Property

Position Overview:

Resident Head Gardener and Caretaker overseeing the care and maintenance of a noted, historic, large private estate in a premier location on the North Shore of Chicago, Illinois.  The property features extensive lawns, native prairie meadows, formal and cutting gardens, numerous specimen trees, a greenhouse, a vegetable garden, fountains, extensive hardscapes, and water features.  In addition to the main house, there are several notable outbuildings. 

This role emphasizes the care, maintenance, and stewardship of a historic property. The successful candidate will act as as both the Caretaker and the Head Gardener for the property, working in close collaboration with the owners (who live at the property) and their key staff members.

 The successful candidate will:

• Understand that the role is focused on care, maintenance, and stewardship of a historic property;
• Have deep knowledge of plants and gardens with a proven record of excellent execution;
• Have a high degree of mechanical competence;
• Be proactive and observant, able to monitor the estate closely and communicate needs before they become problems;
• Be able to take intelligent initiative; and
• Be comfortable working both independently and collaboratively.

 Qualifications:

• 10+ years of hands-on horticultural experience covering a wide range of plant types, ideally on a private estate;
• Strong knowledge of Midwestern planting, including perennial borders, prairie/meadow ecosystems, and vegetable gardening;
• Proven experience with greenhouse propagation, plant care, and seasonal transitions;
• Expertise in organic/sustainable gardening and Integrated Pest Management (IPM);
• Experience with caretaking and household systems (HVAC, lighting, irrigation, security, A/V, and basic appliances, among others);
• High level of discretion and comfort working in a private family setting;
• Excellent communication skills, organized, and detail oriented;
• Proven ability to prioritize tasks, manage time, and manage outside vendors;
• Physically capable of performing manual labor outdoors in all conditions; and
• Valid driver’s license and ability to operate and maintain a wide range of yard and garden equipment (mowers,tractors, snowplows, etc.)

Key Responsibilities:

 Head Gardener Duties

• Perform daily walkthroughs;
• Maintain and care for formal gardens, cutting and vegetable gardens, orchard, greenhouse, meadows, lawns, and native prairie areas;
• Oversee or personally perform mowing, weeding, pruning, trimming, mulching, deadheading, fertilizing, watering, sowing, and harvesting;
• Oversee and coordinate external vendors:
• Maintain and operate property water systems including irrigation and ponds;
• Ensure proper care of all hardscapes, patios, pool decks, and walkways;
• Assist in seasonal cleanups (spring/fall) and snow removal when necessary;
• Support care and protection of fountains, planters, and delicate plantings; and
• Maintain greenhouse, tool sheds, and all gardening areas in clean and organized condition

Caretaker Duties

• Monitor and oversee maintenance of all mechanical and electronic systems at the property;
• Assist with driveway maintenance, garage cleaning, vehicle checks, and seasonal movement of awnings, cushions, and outdoor furniture;
• Keep all tools and equipment in safe, working order, and maintain a clear and logical inventory system;
• Monitor property for any signs of disrepair, leaks, or pest activity and act or escalate appropriately;
• Assist with cleaning attics, basements, and outdoor structures as needed; and
• Provide light support for special events and seasonal projects.

Operational Duties

• Act as a core member of the team, reporting to the Director of Properties;
• Create and follow detailed plans and schedules;
• Create annual budgets and track expenses during the year against the budgets, providing in-person quarterly updates to the owners; and
• Maintain detailed records of all activities