Facilities Manager – Winnetka, IL
Facilities Manager – Winnetka, IL (Multi-Property Oversight: IL, MT, Chicago & Cabo)
We are seeking a highly skilled and hands-on Facilities Manager to oversee the maintenance, operations, and overall functionality of multiple high-end residential properties located in Winnetka, Illinois, with additional residences in Montana, Chicago, and Cabo San Lucas.
The ideal candidate will be mechanically inclined, proactive, and capable of managing a range of complex building systems while ensuring each property is maintained to the highest standards. This position requires strong technical knowledge, vendor management expertise, and the ability to travel as needed.
This is a live-out position based in Winnetka, offering a salary of $120,000–$150,000, full benefits, and flexibility for either full-time employment or contract engagement.
Local and Midwestern candidates are strongly preferred. The position requires approximately 40–50 hours per week, with flexibility for weekends and travel to other properties as needed.
Key Responsibilities
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Oversee and maintain all building systems, including electrical, plumbing, HVAC, and mechanical operations across multiple properties.
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Serve as the primary point of contact for maintenance, repairs, and facility operations.
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Perform hands-on maintenance and troubleshooting — this is an active, involved position rather than a supervisory-only role.
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Coordinate, schedule, and negotiate with vendors and contractors to ensure timely, high-quality work.
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Manage seasonal property preparations (e.g., winterizing systems, snow removal, pool openings/closings, and landscaping coordination).
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Ensure all properties are in “guest-ready” condition at all times.
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Maintain accurate maintenance logs, budgets, and preventive maintenance schedules.
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Provide support for special projects, renovations, and capital improvements.
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Be on-call for emergencies and available for travel between properties as required.
Qualifications & Skills
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Minimum of 5+ years of experience as a Facilities or Property Manager for high-end residential estates or multiple properties.
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Strong technical knowledge of mechanical, electrical, plumbing, and HVAC systems.
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Proven hands-on ability to perform repairs and maintenance independently.
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Excellent project management and vendor coordination skills.
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Highly organized, detail-oriented, and capable of managing multiple priorities simultaneously.
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Strong communication skills and professional demeanor.
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Experience with seasonal property management, including cold and warm climate transitions.
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Valid driver’s license, clean driving record, and ability to travel as needed.
Compensation & Benefits
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Salary: $120,000 – $150,000, commensurate with experience.
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Full benefits package offered.
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Live-out position (housing not provided).
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Flexibility for contract or full-time employment, depending on candidate preference.
