Grounds & Building Caretaker / Estate Maintenance Specialist
Location: Eastern Shore of Maryland
Property Type: Small hotel estate with 8 managed acres, vegetable gardens, historic main house, and six guest cottages
Position Type: Full-time, year-round
Reports To: Property Owner, General Manager, or Inn Manager
Position Overview
We are seeking a dependable, experienced, and hands-on Grounds & Building Caretaker to oversee the day-to-day maintenance of a distinctive small hotel property on the Eastern Shore of Maryland. The property includes 35 acres of which approximately 8 are managed acres of grounds and gardens, productive vegetable gardens, a large historic main house, and six guest cottages. This is a hybrid role requiring strong practical skills in both exterior grounds care and building maintenance, along with the judgment, pride, and professionalism needed to support a high-quality guest experience.
The ideal candidate is comfortable working independently, prioritizing daily needs across multiple buildings and outdoor areas, identifying issues before they become problems, and coordinating with management, housekeeping, vendors, and contractors as needed. This position is best suited to someone who enjoys variety, takes ownership of a property, and understands that excellent maintenance is part of excellent hospitality.
Key ResponsibilitiesGrounds, Landscaping & Exterior Presentation
· Maintain the overall appearance, safety, and cleanliness of approximately 8 managed acres, including lawns, pathways, drives, parking areas, guest-facing outdoor spaces, and service areas.
· Mow, trim, edge, weed, mulch, prune, rake, water, and perform seasonal cleanup to keep the property attractive and well cared for.
· Maintain flower beds, shrubs, trees, hedges, and planted areas with attention to guest presentation and seasonal interest.
· Operate and maintain lawn and grounds equipment, including mowers, string trimmers, blowers, hedge trimmers, hand tools, and related machinery.
· Monitor irrigation, drainage, erosion, storm debris, lighting, signage, fencing, gates, and exterior furniture for repair or replacement needs.
· Assist with snow, ice, storm, and emergency weather preparation and cleanup as needed.
Vegetable Gardens
· Support the planning, planting, upkeep, and seasonal rotation of vegetable gardens in coordination with management or culinary staff.
· Prepare beds, amend soil, plant, weed, water, mulch, trellis, harvest, and maintain garden areas so they remain productive and visually appealing.
· Monitor plants for pests, disease, irrigation needs, nutrient deficiencies, and weather-related stress.
· Maintain garden tools, compost areas, hoses, irrigation components, storage spaces, and related supplies in clean and organized condition.
· Communicate harvest availability, garden issues, and seasonal needs to the appropriate manager.
Building Maintenance: Historic Main House & Six Guest Cottages
· Perform routine and preventive maintenance for the historic main house, six cottages, and associated outbuildings or service areas.
· Address basic plumbing, electrical, carpentry, painting, drywall, hardware, locks, windows, doors, screens, fixtures, appliances, and general repair needs within skill level.
· Respond promptly to guest-comfort issues, urgent maintenance requests, and turnover-related repairs in coordination with housekeeping and management.
· Inspect buildings regularly for leaks, moisture, pest entry, structural concerns, trip hazards, equipment issues, and other signs of deterioration.
· Use an appropriate, careful approach when working on the historic main house, preserving original materials where possible and escalating specialized repairs to qualified tradespeople.
· Maintain mechanical, storage, utility, workshop, and equipment areas in an orderly and safe condition.
Property Operations, Safety & Vendor Coordination
· Walk the property regularly to identify maintenance needs, safety concerns, and appearance issues before they affect guests.
· Prioritize daily tasks based on guest arrivals, property events, seasonal conditions, weather, and management direction.
· Coordinate with outside contractors, landscapers, tradespeople, inspectors, and service providers when specialized work is required.
· Maintain basic maintenance records, supply lists, equipment service notes, and completed-task logs as requested.
· Follow safe work practices and comply with applicable property policies, equipment instructions, and local requirements.
· Represent the property professionally when visible to guests, including offering courteous assistance or direction when appropriate.
· Participate in required on-call coverage for urgent maintenance, guest-comfort issues, weather events, security-related property concerns, and emergency repairs outside normal working hours, with the ability to acknowledge urgent calls or messages within 10 minutes and resolve issues within 30 minutes when required.
Qualifications
· Minimum of 3–5 years of experience in property maintenance, estate care, hospitality maintenance, facilities maintenance, landscaping, groundskeeping, or a closely related role.
· Practical experience maintaining both buildings and grounds; experience with historic homes, inns, farms, estates, boutique hotels, or high-end residential properties is strongly preferred.
· Working knowledge of lawn care, pruning, seasonal cleanup, basic horticulture, irrigation, and garden maintenance.
· Comfort performing basic plumbing, carpentry, painting, hardware, fixture, appliance, and general repair tasks.
· Ability to operate and maintain grounds equipment safely and responsibly.
· Valid driver’s license and reliable transportation.
· Ability to lift, carry, push, pull, bend, climb, kneel, and work outdoors in varying weather conditions.
· Strong judgment, reliability, attention to detail, and ability to work independently without constant supervision.
· Professional demeanor and comfort working around guests, staff, vendors, and ownership.
· Required ability and willingness to participate in on-call duties, including timely response to urgent property and guest-related maintenance needs, with acknowledgement of urgent calls or messages within 10 minutes and issue resolution within 30 minutes when required.
Preferred Skills or Certifications
· Experience with vegetable gardens, edible landscapes, composting, soil health, or small-scale food production.
· Experience maintaining older or historic structures, including sensitivity to original materials and preservation-minded repairs.
· Basic HVAC troubleshooting, pool or spa maintenance, small-engine repair, irrigation repair, or equipment maintenance experience.
· Maryland pesticide applicator license, horticulture training, OSHA safety training, or related certifications are a plus but not required.
· Ability to trailer, tow, or operate larger equipment such as compact tractors, utility vehicles, or similar machinery is helpful.
Work Schedule
This is a full-time, year-round position. The typical schedule is daytime hours, with flexibility required during peak guest seasons, storms, special events, urgent repairs, snow or ice events, and seasonal planting or cleanup periods. Days of the week vary – not a Monday – Friday position. On-call availability is required for urgent guest-comfort issues, weather-related property needs, emergency repairs, and other time-sensitive maintenance concerns outside normal working hours. During on-call periods, the employee must acknowledge urgent calls or messages within 10 minutes and resolve issues within 30 minutes when required.
Compensation
Expected compensation is commiserate with experience, skills, certifications, schedule expectations, and required on-call duties. Candidates with strong horticulture experience, historic-property maintenance skills, independent estate-management ability, and reliable emergency-response availability should be considered at the higher end of the range.
Benefits
Benefits may include paid time off, seasonal flexibility, use of property equipment for work duties and health insurance support. Final benefits should be confirmed based on the property’s employment policies.
About the Ideal Candidate
The right person for this role is practical, observant, organized, and steady under pressure. They take pride in making a property look cared for every day, enjoy both outdoor work and hands-on repairs, and understand how maintenance decisions affect guest comfort, safety, and the reputation of a small hospitality business. This role requires someone who can notice what needs doing, communicate clearly, and follow through.
How to Apply
Interested candidates should submit a resume or work history summary via the platform, a brief description of relevant maintenance and groundskeeping experience, and at least two professional references. Applicants are encouraged to describe experience with historic buildings, hotels or inns, estate properties, vegetable gardens, landscaping equipment, and independent property care.
Job Type: Full-time
Pay: $45,000.00 - $65,000.00 per year
Benefits:
- Health insurance
- Paid time off
Education:
- High school or equivalent (Required)
Experience:
- Groundskeeping and maintenance: 3 years (Required)
Language:
Ability to Commute:
- Chestertown, MD 21620 (Required)
Ability to Relocate:
- Chestertown, MD 21620: Relocate before starting work (Required)
Work Location: In person
