Groundskeeper & Property Caretaker

Location: Worton, MD (Chesapeake Bay Waterfront Estate)
Job Type: Full-Time, Year-Round
Housing: Onsite home available; living onsite strongly preferred

Position Overview

A private family is seeking a dedicated, skilled, and service-oriented Groundskeeper & Property Caretaker to support the operations of a 3,000-acre Chesapeake Bay waterfront estate in Worton, Maryland. Approximately 5 acres are highly maintained and require regular care, while the remainder includes farmland, woodlands, and natural landscapes. This role works closely with—and reports to—the long-tenured Farm Manager, with frequent interaction with the Owner and seasonal engagement with their grown children and extended family. The position offers long-term stability and the opportunity to grow into a future Estate & Property Manager role through hands-on training and mentorship.

The Property

The estate sits on Maryland’s Eastern Shore, spanning over 3,000 acres. Approximately 5 acres surrounding the main residence are meticulously maintained. A long, private, well-kept road provides access to the property and a small number of seasonal homes and staff residences. The Owner resides on the property full-time, while adult children and their families visit seasonally.

The Family

The estate has been in the family for many years. The 88-year-old Owner maintains an active lifestyle, traveling regularly to Washington, DC, domestically, and occasionally internationally. They value long-term, respectful relationships with household, garden, and office employees. The Groundskeeper & Property Caretaker will interact regularly with the Owner, collaborate closely with the Farm Manager, and support both the Owner and the next generation who visit seasonally.

Key Responsibilities

Groundskeeping & Landscaping

• Perform lawn care, mowing, edging, weeding, mulching, leaf management, and seasonal landscape tasks

• Operate lawn mowers, tractors, and other equipment (no special license required)

• Assist with planting, pruning, irrigation oversight, and general outdoor upkeep

• Support broader farm-related grounds projects as needed

Estate & Property Management Training

• Work under the Farm Manager to develop skills in property and estate operations

• Assist with vendor and contractor coordination, equipment maintenance, seasonal planning, and project oversight

• Participate in mentorship aimed at developing into a future Estate & Property Manager role

• Optionally learn introductory aspects of farm management

Vehicle Care

• Keep estate vehicles consistently washed, tidy, fueled, and ready for use

Mail & Errand Support

• Retrieve daily mail and packages from the farm office

• Deliver items to the residence as needed

House Maintenance & Support

• Assist with basic maintenance tasks, including light bulb replacement, trash removal, and mechanical system checks

• Support housekeeper when needed to maintain smooth household operations

Pool & Tennis Court Maintenance

• Oversee routine maintenance and seasonal care of the estate’s pool and tennis court

Ad Hoc Projects

• Complete various property, home, yard, and farm projects as requested by the Owner or Farm Manager

• Demonstrate flexibility and willingness to take on a wide range of responsibilities

Qualifications

• Proficiency with yard and grounds equipment; tractor experience preferred

• Pool maintenance experience helpful

• Strong problem-solving skills and the ability to collaborate effectively

• Excellent interpersonal skills and professionalism when interacting with the Owner, family members, vendors, and staff

• High discretion and respect for privacy

• Positive attitude, sense of humor, and ability to thrive in a rural, team-oriented environment

• Willingness to undertake hands-on tasks and maintain a strong work ethic

• Dependability and desire for long-term employment

Compensation & Benefits

• Pay: Market, commensurate with experience

• Health, dental, and vision insurance

• Paid Time Off (sick and leisure)

• Full-time schedule, 5 days per week

• Onsite housing available; relocation support considered

• Covid vaccination not required

Additional Requirements

• Ability to reliably commute to Worton, MD, or relocate to onsite housing

• Comfort working in a private, rural estate environment with long-term stability

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