PROPERTY MANAGER and Groundskeeper

| Litchfield, CT, United States

Posted Date 4/03/2026
Description

Overview

A unique opportunity for a skilled and dedicated Property Manager and Groundskeeper to oversee the care and maintenance of a bucolic 60-acre private estate in Litchfield County, Connecticut. The Caretaker role is integral to the maintenance, security, and overall management of the property, and encompasses a wide range of duties including ongoing maintenance and repairs, groundskeeping, garden oversight, contractor oversight, and ensuring security measures are functioning properly at all times. The ideal candidate is highly organized and proactive with a wide range of skills who can work independently and thoughtfully to ensure the property is well managed and expertly maintained. The PM will oversee a small support staff and should have experience in that regard.

Key Responsibilities

Oversight and Reporting

The Property Manager reports to the Family Office Manager of ongoing requirements to coordinate and facilitate their responsibilities as Property Manager. This includes all financial requests as well as third party contract execution.

Maintenance and Repairs

  • Perform ongoing general maintenance and repair work inside and outside.
  • Have skills with tools and construction knowledge
  • Knowledge of plumbing, electrical, and related home trades
  • Ensure all home systems are operational, including plumbing, electrical, and HVAC.
  • Maintain, schedule, service and repair equipment, systems and supplies as necessary.
  • Maintain all driveways and pathways to ensure they are clear and safe for use year-round.
  • Maintain and clean garages and storage buildings, as well as utility vehicles

Groundskeeping and Garden

  • Ensure grounds and gardens are immaculately maintained including shrubbery and green areas.
  • Manage garden maintenance providers and collaborate as needed.
  • Oversee and assist occasionally in seasonal planting and harvesting.
  • Perform and oversee tree care, garden, landscape, and driveway maintenance.

Security

  • Ensure all security measures are in place and functioning properly.
  • Monitor alarm systems, internet, Wi-Fi, and audio-visual systems and ensure functionality at all times.

Seasonal Responsibilities

  • Perform winter maintenance, flag edges and snow removal from driveways, walks, and entrances.
  • Secure seasonal furniture and store cushions
  • Manage deer fencing to protect yew, holly hedges and susceptible foliage.
  • Oversee pruning and treatment of orchard
  • Mow tall grass fields as needed.
  • Clean up leaves, garden waste and fallen trees/limbs and mulch
  • Ensure all gutters and drains are clean of debris.
  • Collaborate with gardener for fall leaf cleanup and composting.

Pest Control

  • Address and mitigate insect problems (beetles, centipedes, ants, etc.)
  • Trap rodents and clean out spiders/cobwebs in high traffic areas.
  • Place and check rodent traps regularly and replace as necessary.
  • Oversee contractors to spray for mosquitoes and tick control

Home Systems: Routine Tasks, Oversight and Inspections

  • Test and ensure good operation of hot water, faucets, taps, toilets, and softener/filtration systems.
  • HVAC: Maintain heating fuel/AC filters, manage service provider and schedule maintenance.
  • Generators: Ensure adequate fuel and good working order. Schedule semiannual maintenance.
  • Alarm/Internet-WIFI/Audio-Video: Ensure uptime performance and schedule maintenance.
  • Coordinate with contractors for large service and maintenance projects and supervise their work.
  • Maintain system fuel requirements and scheduled maintenance.

Additional Responsibilities

  • Receive and manage mail, including letters, parcels, and packages.
  • Collect and dispose of trash and recyclables daily.
  • Perform daily pool maintenance and operation during season, including testing and cleaning. Manage seasonal opening and closing.
  • Ensure irrigation systems are leak-free and functioning properly, working with the gardener to make seasonal adjustments.
  • Maintain all outdoor kitchen appliances and ensure they are clean and in good working order
  • Maintain, clean and organize all garages, storage and gardening sheds
  • Ensure/acquire supplies for houses to insure they are adequately stocked.
  • Create and maintain comprehensive service records of all house and property systems.

Skills and Qualifications

  • Experience in building maintenance, including plumbing, electrical, and HVAC systems.
  • Hands-on skills in general construction and repair, systems and appliance maintenance
  • Gardening and operation of plowing and landscaping equipment.
  • Strong problem-solving, time management, and communication skills.
  • Experience with time management records and software to ensure all maintenance is coordinated and organized for rapid repair and efficiency. Each workday must have a prioritized "To Do" list, that reflects the order of repairs and what was accomplished for that day.
  • High degree of personal integrity, reliability, and trustworthiness.
  • Understanding of equipment and systems upkeep and maintenance, including annual service and repairs.
  • Maintain, clean, sharpen, lubricate and repair tools, vehicles and equipment.

Ideal Candidate

  • Highly organized and experienced property manager with stellar references
  • Proven experience in property management, groundskeeping, and landscaping.
  • Enjoys operational freedom and can manage schedules to accomplish set goals on a daily basis
  • Takes pride in their work and is a thoughtful decision maker.
  • Capable and willing to manage property as the lead of a small, dedicated team.
  • Hands-on role in reducing the need for small repairs performed by outside contractors.
  • Is a US Citizen or has a green card, no criminal history and will submit to a background check.
  • Clean driver’s license and ability to operate various types of equipment and vehicles
  • Has excellent work, as well as personal, references.
  • Is in a stable relationship and prepared to live on property full time.
Job Type
Full-Time
Job Categories
Groundskeeper | Property Maintenance or Manager
Housing
Live-in or On-site
Compensation
$90K for the right person with full health insurance. Generous vacation time. 3200 sq ft caretaker house on its own 4 acre wooded site is provided as part of the package.

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