Caretaking Couple, Fort Myers Area, Florida

Caretaking Couple

Fort Myers Area, Florida (Live-In)

Salary: $150,000–$180,000 (DOE) + Full Benefits + Private Residence

A wonderful, multigenerational family with a beautiful waterfront estate in the Fort Myers area is seeking an experienced, service-minded Domestic Caretaking Couple to become a long-term part of their household.

This is an exceptional opportunity to join a family that is genuinely kind, respectful, and deeply appreciative of their staff. There is very little turnover within the household, and the family is looking for a couple seeking longevity—individuals who will naturally integrate into the family environment, take ownership of the estate, and enjoy supporting one family for many years to come.

The compound encompasses approximately 14,000 square feet of combined living space, including the primary residence, guest cottage, and pool pavilion, situated on significant waterfront acreage.

The home is staffed year-round, and has a full-time Garden team. The successful couple will work alongside these valued team members while assuming responsibility for the day-to-day presentation, operation, preventative maintenance, and overall care of the estate.

Responsibilities

Property & Estate Management

• Conduct daily walkthroughs of all residences, guest accommodations, and outbuildings.
• Ensure the entire estate remains in pristine, guest-ready condition at all times.
• Oversee preventative maintenance programs for the residence and all supporting infrastructure.
• Coordinate and supervise vendors, contractors, service providers, and maintenance professionals while holding them accountable for quality, scheduling, and workmanship.
• Monitor generators, HVAC systems, water filtration, irrigation, lighting, security systems, pool equipment, and all mechanical systems to ensure they are operating efficiently.
• Maintain detailed maintenance records, warranties, service schedules, and comprehensive household inventories, ensuring all records remain current and organized.
• Create, maintain, and continually update the estate's House Manual, including detailed Standard Operating Procedures (SOPs), emergency procedures, household systems, vendor information, family preferences, and comprehensive arrival and departure guides for family members and guests.
• Take a proactive ownership approach by identifying and resolving issues before they become problems.

Waterfront Property Responsibilities

• Understand the unique demands associated with maintaining a waterfront estate.
• Protect the residence, mechanical systems, outdoor furnishings, and equipment from the effects of saltwater and the coastal environment.
• Oversee the care, preventative maintenance, and presentation of the family's vehicles and watercraft.
• Ensure all vehicle and vessel registrations, licensing, servicing, inspections, and maintenance schedules remain current.
• Previous experience maintaining boats and watercraft, including seasonal maintenance and coordinating repairs, would be highly advantageous, although not essential.
• Understand shoreline maintenance, erosion, retaining walls, drainage systems, and hurricane preparedness.
• Coordinate storm preparation, evacuation procedures, and post-storm recovery to protect both the property and its assets.

Interior Household Support

• Maintain the primary residence and guest accommodations in a beautifully presented, welcoming condition.
• Prepare the estate in advance of family arrivals, holidays, and special occasions.
• Create a warm, relaxed, family-centric atmosphere for principals, family members, and guests.
• Work alongside the housekeeping team to maintain exceptional presentation standards throughout the home.
• Assist with table service and entertaining when required.
• Assist the Chef with simple meal preparation when requested.
• Run errands, grocery shop, collect prescriptions, receive deliveries, and chauffeur family members to and from the airport as needed.

Grounds & Exterior

• Work alongside the existing gardening team to ensure the grounds remain beautifully maintained.
• Coordinate landscaping vendors and irrigation maintenance.
• Assist with seasonal projects and exterior upkeep as needed.
• Continually monitor the property to ensure every aspect of the estate reflects the highest standard of presentation.

The Ideal Couple

The successful couple will be hands-on, proactive, mechanically inclined, and genuinely enjoy estate living. They should possess excellent common sense, outstanding communication skills, and a natural hospitality mindset. Above all, they will understand that private service is about anticipating needs, taking ownership, and creating an environment where the family can simply relax and enjoy their home.

This is not a "clock-in, clock-out" position. The family is seeking a couple with a genuine ownership mentality—individuals who naturally notice what needs attention, communicate proactively, and take pride in ensuring the estate operates seamlessly throughout the year.

The ideal couple will be highly organized administrators who enjoy creating systems and maintaining detailed documentation. They should be confident maintaining household inventories, updating records, refining the House Manual, and continually improving the estate's Standard Operating Procedures to ensure consistency and seamless operation regardless of who is in residence.

Candidates should also be confident with technology and comfortable operating today's latest smart home systems. Experience with integrated home automation platforms such as Savant, Control4, Crestron, Lutron, advanced security systems, surveillance, gate access, Wi-Fi networks, lighting controls, HVAC automation, entertainment systems, and similar technologies would be highly desirable. The ability to quickly learn new technology is equally important.

The family values individuals who are humble, approachable, friendly, naturally hospitable, and genuinely enjoy working together. The ideal couple will know when to engage with family and guests and when to quietly work behind the scenes.

Outstanding longevity within previous private households is essential and will be a significant consideration during the selection process.

Conversational Spanish would be considered an advantage but is not required.

A connection to the Fort Myers area, or a genuine desire to make Southwest Florida a long-term home, would be viewed favorably.

Schedule

During the quieter summer months (May through September), the schedule is generally Monday through Friday, allowing the couple to focus on preventative maintenance, projects, organization, and preparing the estate for the upcoming season.

From October through April, when the family is in residence, flexibility is essential. Weekend coverage and holiday coverage will occasionally be required, and the successful couple should be comfortable adjusting their schedule to meet the family's needs during this busy period. The family fully appreciates the additional commitment required during the season and values professionals who embrace a true hospitality mindset.

Compensation & Benefits

• Annual salary of $150,000–$180,000, depending on experience.
• Comprehensive medical, dental, and vision insurance.
• Two weeks of paid vacation annually.
• One week of paid sick leave.
• Beautiful private three-bedroom, two-and-a-half-bath residence located on the estate, complete with its own private entrance and porch.
• Possible relocation assistance.
• Long-term opportunity with an exceptional family that genuinely values loyalty, professionalism, and mutual respect.

This is an exceptional opportunity for an experienced domestic couple seeking a long-term position with a gracious family who genuinely appreciates and values the people who support them. If you enjoy maintaining a beautiful waterfront estate, have a hands-on ownership mentality, take tremendous pride in your work, and are looking for a place to call home for many years to come, this truly is a dream opportunity.

The family is seeking more than employees—they are looking for trusted professionals who will become an integral part of their household and help preserve their estate to the highest standards while creating a warm, welcoming environment for generations of family and friends to enjoy.

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