Property Manager & Caretaker – Private Waterfront Estate

Chesapeake City, Maryland | Full-Time | Live-In | Year-Round

Private Family Estate | Approximately 800 Acres | Housing Provided

Position Overview

A wonderful opportunity is available for an experienced, hands-on Property Manager & Caretaker to oversee a beautiful, historic waterfront estate in the Chesapeake City area of Maryland.

Our clients are a private family with a long-standing connection to this approximately 800-acre property, which includes waterfront access, wooded areas, open fields, private residences, barns, workshops, and various outbuildings.

The family is looking for someone who genuinely enjoys working outdoors, takes pride in maintaining a beautiful property, and has the practical skills, common sense, and initiative to manage the day-to-day responsibilities of a large private estate.

This is very much a hands-on position, combining property maintenance, groundskeeping, equipment care, vendor coordination, and general oversight. The successful candidate will be the family's primary point of contact on the property, ensuring everything is maintained, secure, and ready for family visits throughout the year.

We are looking for someone who is resourceful, dependable, organized, and comfortable working independently. Someone who can identify a problem, figure out the best solution, and either take care of it personally or coordinate the appropriate professional.

This is an excellent opportunity for someone seeking a long-term position with a private family who values loyalty, discretion, and pride in one's work.

Responsibilities

Property Maintenance & General Repairs

• Oversee the daily care and maintenance of private residences, barns, garages, workshops, and additional buildings.

• Perform hands-on maintenance, including carpentry, painting, minor plumbing, basic electrical troubleshooting, and general repairs.

• Monitor and maintain property systems, including water, septic, HVAC, generators, and associated infrastructure.

• Establish and follow preventive maintenance schedules to ensure the property and equipment remain in excellent condition.

• Identify maintenance concerns early and coordinate qualified contractors for specialized repairs.

Grounds, Land & Waterfront Maintenance

• Maintain and oversee approximately 800 acres of fields, wooded areas, trails, private roads, and landscaped grounds.

• Perform and coordinate mowing, trimming, brush clearing, tree maintenance, firewood preparation, and seasonal cleanup.

• Maintain safe access throughout the property, including private lanes, walking trails, and outdoor recreational areas.

• Monitor shoreline conditions, beach access, docks, piers, and waterfront structures.

• Operate and maintain tractors, ATVs, mowers, chainsaws, and other property equipment.

• Keep workshops, tools, machinery, and storage areas clean, organized, and properly maintained.

Vendor Management & Project Coordination

• Source, schedule, and oversee independent contractors for landscaping, construction, repairs, tree work, and property improvements.

• Obtain estimates, coordinate approved projects, and monitor quality, timelines, and expenses.

• Maintain records of completed work, invoices, maintenance schedules, and equipment servicing.

• Communicate clearly with the family regarding property needs, ongoing projects, and recommended improvements.

• Be comfortable managing projects from start to finish while remaining personally involved in the day-to-day work.

Family Visits & Property Readiness

• Prepare the property and residences for family visits, ensuring everything is clean, organized, safe, and ready for arrival.

• Coordinate housekeeping, linens, household supplies, outdoor furniture, and general preparations.

• Maintain beach areas, docks, outdoor entertaining spaces, and recreational facilities.

• Assist with general household and property needs when the family is in residence.

• Following visits, ensure the residences and grounds are properly cleaned, secured, and returned to their normal condition.

• Respect the family's privacy and understand the importance of discretion when working on a private estate.

Security, Administration & Seasonal Care

• Monitor the property for maintenance concerns, storm damage, unauthorized access, and potential safety issues.

• Respond appropriately to weather-related emergencies, outages, and urgent property needs.

• Maintain organized records, work logs, inventories, receipts, and maintenance schedules.

• Provide regular updates to the family or their designated representatives.

• Plan and manage seasonal responsibilities, including spring opening, summer maintenance, fall preparation, and winter property protection.

Candidate Requirements

We are looking for a capable, practical individual who understands the responsibilities of caring for a large private property and enjoys being hands-on.

• Minimum 5–10 years of relevant experience in estate management, property maintenance, farming, groundskeeping, facilities management, or a skilled trade.

• Strong practical knowledge of carpentry, general repairs, plumbing, electrical troubleshooting, and mechanical maintenance.

• Confident operating tractors, ATVs, mowers, chainsaws, and other property equipment.

• Experience managing independent contractors, coordinating projects, and maintaining budgets.

• Comfortable working outdoors throughout the year in varying weather conditions.

• Physically capable of performing the responsibilities associated with maintaining a large rural property, with reasonable accommodation where applicable.

• Organized, resourceful, dependable, and able to work independently without constant supervision.

• Excellent communication skills and a clear command of English.

• Valid driver's license and a responsible driving history.

• Professional, discreet, trustworthy, and respectful of family privacy.

• Must have excellent, verifiable professional references.

• Must be legally authorized to work in the United States.

A background in private estate management, farming, agricultural properties, waterfront estates, or large rural properties would be particularly attractive.

Schedule, Housing, Compensation & Benefits

• Position: Full-Time Property Manager & Caretaker

• Location: Chesapeake City, Maryland

• Annual Salary: $75,000–$95,000, depending on experience and qualifications

• Schedule: Full-time, year-round, with flexibility based on seasonal demands and family visits

• Housing: Private on-site caretaker residence provided

• Paid Vacation: Two weeks annually

• Paid Sick Leave: One week annually

• Paid Holidays: National holidays, with flexibility around family visits and property requirements

• Medical Benefits: Flexible employer contribution toward medical insurance, to be discussed

• Start Date: To be discussed

The successful candidate will be required to reside on the property. Housing arrangements and associated terms will be discussed during the interview process.

The Ideal Candidate

The ideal person for this position is someone who enjoys the outdoors, appreciates the beauty of a historic property, and takes genuine pride in keeping everything running smoothly.

Someone who is just as comfortable operating a tractor, clearing a fallen tree, repairing a fence, or maintaining equipment as they are coordinating contractors, managing a project, or communicating with the family.

We are not looking for someone who simply delegates responsibilities. This is a hands-on role for someone with practical skills, initiative, common sense, and a willingness to roll up their sleeves.

A positive attitude, good judgment, flexibility, and a genuine interest in establishing a long-term relationship with the family are essential.

How to Apply

Qualified candidates with relevant property management, maintenance, or estate experience are encouraged to apply.

Please submit a current resume outlining your experience, particularly with large properties, equipment operation, hands-on maintenance, and contractor management.

Excellent professional references will be required.

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