This position is ideal for someone who finds satisfaction in building, repairing, maintaining, improving, and caring for exceptional properties while becoming a trusted member of a family's long-term team.
A Unique Career Opportunity
We are seeking an experienced, trustworthy, and highly motivated Private Estate Manager & Head Caretaker to oversee the maintenance, appearance, and day-to-day operation of our private family estate, two nearby rental properties, and related grounds.
This position combines the responsibilities of an estate manager with those of a skilled, hands-on caretaker. The successful candidate will personally perform much of the property's maintenance, groundskeeping, seasonal work, and day-to-day care while coordinating outside contractors when specialized work or additional assistance is required.
This is far more than a maintenance position. It is a long-term career opportunity for someone who enjoys working with their hands, takes genuine pride in exceptional workmanship, anticipates needs before they arise, and is committed to maintaining beautiful properties to the highest standards.
Our goal is to find someone looking for a long-term career—not simply their next job. We hope to develop a relationship built on mutual trust and respect with an individual who will take genuine pride in caring for our family's properties for many years. As trust is earned, the responsibilities and opportunities associated with this position are expected to grow.
Primary Responsibilities:
Estate Operations & Property Management
- Conduct routine inspections of all properties to ensure they remain in exceptional condition.
- Personally perform routine maintenance whenever practical while coordinating qualified contractors for specialized work or projects requiring additional expertise.
- Proactively identify maintenance concerns before they become costly repairs.
- Coordinate and oversee outside contractors to ensure quality workmanship and timely completion of projects.
- Maintain organized records of repairs, warranties, maintenance schedules, and service history.
- Recommend improvements that enhance the appearance, functionality, and long-term value of the properties.
- Ensure each property is consistently clean, organized, secure, and ready for family members or guests.
Grounds & Landscape Care
- Personally maintain the lawns at the two rental properties, including mowing, edging, trimming, fertilizing, seasonal cleanup, and general landscape care.
- Oversee landscape maintenance at the primary residence by regularly inspecting the work of outside contractors and ensuring it meets the family's standards.
- Maintain flower beds, shrubs, trees, gardens, orchard areas, and landscaped grounds.
- Operate, maintain, and adjust irrigation systems.
- Perform pruning, planting, fertilization, weed control, and seasonal landscape improvements.
Greenhouse, Garden & Orchard Management
- Operate and maintain the estate greenhouse.
- Start flowers, vegetables, and other plants according to the owners' direction.
- Assist with planting, harvesting, and maintaining gardens, orchard areas, and farmland.
- Monitor greenhouse equipment and growing conditions to ensure healthy plant production.
Seasonal Property Maintenance
- Personally assist with and coordinate snow removal to maintain safe access to all properties.
- Keep driveways, sidewalks, walkways, and entrances clear of snow and ice.
- Winterize irrigation systems and prepare each property for seasonal changes.
- Monitor weather conditions and proactively prepare the properties before storms whenever practical.
Vehicle & Equipment Care
- Ensure family vehicles are clean, fueled, and ready for use.
- Coordinate outside vehicle washing and detailing services.
- Monitor maintenance schedules, registrations, inspections, tire pressures, and fluid levels.
- Schedule maintenance and repairs while maintaining accurate service records.
- Maintain trailers, lawn equipment, power tools, the rototiller, and other estate equipment in clean, organized, and ready-to-use condition.
Building & Facility Maintenance
- Perform routine maintenance and minor repairs on homes, garages, outbuildings, fences, gates, lighting, irrigation systems, and related infrastructure.
- Coordinate licensed contractors when specialized repairs are required.
- Maintain workshops, garages, storage buildings, and mechanical spaces in an orderly and professional manner.
- Maintain an organized inventory of maintenance supplies and equipment.
Seasonal & Holiday Estate Projects
- Assist with the installation, maintenance, removal, and organized storage of seasonal and holiday decorations.
- Prepare the estate for holidays, family gatherings, and special events.
- Decorate interior and exterior areas as directed by the owners.
- Ensure seasonal decorations and equipment remain organized, protected, and ready for future use.
Special Projects & Family Business Support
- Provide occasional assistance with projects involving the family's businesses when requested.
- Assist with equipment movement, deliveries, facility improvements, inventory organization, and other operational projects.
- Demonstrate flexibility and a willingness to contribute wherever assistance is needed while maintaining the same high standards expected throughout the estate.
The Person We Are Looking For
The ideal candidate enjoys physical work, notices details others overlook, takes initiative without being asked, and treats every task as though caring for their own property.
You should be:
- Honest, dependable, and trustworthy.
- Organized and highly self-motivated.
- Comfortable working independently with minimal supervision.
- Mechanically inclined with strong problem-solving abilities.
- Professional, courteous, and respectful.
- Physically capable of lifting, climbing, bending, operating equipment, and working outdoors throughout the year.
- Comfortable performing hands-on work while coordinating contractors when appropriate.
- Able to prioritize multiple responsibilities while maintaining exceptional attention to detail.
- Flexible, resourceful, and willing to assist wherever needed.
Preferred Qualifications
- Previous experience maintaining a private estate, luxury residence, ranch, farm, or similar property.
- Strong knowledge of landscape maintenance, irrigation systems, and general property maintenance.
- Greenhouse or gardening experience is highly desirable.
- Basic carpentry, plumbing, electrical, and mechanical repair skills.
- Experience operating lawn and landscape equipment.
- Bilingual (English/Spanish) candidates are strongly preferred
- Valid driver's license with an excellent driving record.
Compensation & Benefits
- Annual salary of $75,000–$85,000, depending on experience and qualifications (DOE).
- Discretionary annual performance bonus based on initiative, stewardship of the estate, reliability, quality of work, and overall contribution.
- Company truck provided for business use.
- Paid Time Off (PTO).
- Health insurance and other employer-provided benefits.
- Company-provided tools and equipment.
- Long-term career opportunity with a stable, respectful family that values integrity, initiative, craftsmanship, and loyalty.
Additional Expectations
Because this position requires a high level of trust, flexibility, and personal responsibility, it is expected to be your only professional commitment.
Applicants should have:
- Reliable transportation to and from work.
- Established childcare arrangements, if applicable, that allow dependable attendance.
- The flexibility to occasionally adjust work hours for seasonal projects, weather events, or special family needs.
- An unwavering commitment to confidentiality and the privacy of the family.
- No outside employment or side businesses that interfere with the responsibilities of this position.
Pre-Employment Screening
Because this position involves access to private residences, vehicles, equipment, confidential information, and significant responsibility, the successful candidate must successfully complete a comprehensive pre-employment screening process, including:
- Comprehensive criminal background investigation
- Credit history review
- Pre-employment drug screening
- Employment verification
- Professional and personal reference verification
- Motor vehicle driving record review
Integrity, honesty, discretion, professionalism, and sound judgment are essential qualifications for this position.
Why This Position Is Different
This role is about stewardship rather than simply completing assigned tasks. We are looking for someone who takes genuine ownership of the appearance, maintenance, and day-to-day operation of our properties. You will work with your hands every day while also serving as a trusted caretaker, problem solver, and representative of our family.
We understand that exceptional people are difficult to find, and we are prepared to invest in the right individual.
If you are looking for more than just another job—if you are looking for a long-term career where your integrity, initiative, craftsmanship, and commitment to excellence will be genuinely appreciated—we would welcome the opportunity to meet you.
We are seeking someone who takes pride in doing things the right way, enjoys meaningful work, values long-term relationships, and wants to become a trusted member of our family's team.
Pay: $75,000.00 - $85,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Dental insurance
- Employee assistance program
- Flexible spending account
- Health insurance
- Health savings account
- Life insurance
- Paid time off
- Vision insurance
Work Location: In person
