Groundskeeper

Westover School; Middlebury (CT); On-site; USD 33,062 - 37,195; Full time

Benefits offered by this job

Health insurance

Vision insurance

Dental reimbursement

HRA

Employer-paid life insurance

403(b) retirement plan with employer

Professional development opportunities

Job summary

Westover School in Middlebury, CT seeks a dedicated Groundskeeper to maintain lawns, gardens, trees, and outdoor spaces year-round. You will operate landscaping equipment, assist with snow removal, perform light maintenance on tools, and help support campus events while upholding safety standards.

The role is full-time, 12-month, outdoors in various weather conditions; a valid driver's license and prior groundskeeping experience are preferred.

Qualifications

• High school diploma or equivalent preferred.
• 1+ year of professional landscaping/groundskeeping preferred.
• Experience operating commercial landscaping equipment.
• Valid driver's license with acceptable driving record.
• Ability to work outdoors in varied weather.

Responsibilities

• Maintain lawns, gardens, shrubs, trees, and landscaped areas.
• Operate and maintain landscaping equipment.
• Assist with snow and ice removal.
• Monitor irrigation and report maintenance needs.
• Support campus events and general facilities tasks.
• Ensure safety and proper PPE use.

Skills

Landscaping

Equipment operation

Power tools

Attention to detail

Independent worker

Team collaboration

Valid driver’s license

Education

High school diploma or equivalent

Tools

Commercial landscaping equipment

Power tools

Job description

About UsWestover School is a gender-inclusive girls boarding and day school serving grades 9–12. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes meaningful student-adult interaction. Through our programs and dedicated faculty and staff, Westover empowers students to become confident, connected adults who lead lives of purpose and understand the value of relationships, diversity, and making a positive difference in the world.

Job Title: Groundskeeper Department: Facilities Reports to: Director of Facilities Location: Middlebury, Connecticut Position Type: Full-Time, 12 month

About UsWestover School is a gender-inclusive girls boarding and day school serving grades 9–12. We are committed to providing a college preparatory education in a small community atmosphere that emphasizes meaningful student-adult interaction. Through our programs and dedicated faculty and staff, Westover empowers students to become confident, connected adults who lead lives of purpose and understand the value of relationships, diversity, and making a positive difference in the world.

Job SummaryWestover School is seeking a dedicated and skilled Groundskeeper to maintain the beauty, safety, and functionality of our campus grounds. This position is responsible for the care and maintenance of lawns, gardens, trees, athletic and recreational areas, walkways, and landscaped spaces, ensuring the campus remains attractive, welcoming, and safe throughout the year. The Groundskeeper also assists with seasonal projects, snow removal, equipment maintenance, and general facilities support as needed.

Responsibilities And Duties

• Maintain lawns, gardens, shrubs, trees, and landscaped areas through mowing, trimming, edging, planting, watering, fertilizing, pruning, and mulching.
• Operate and maintain landscaping equipment including zero-turn mowers, trimmers, blowers, chainsaws, hedge trimmers, and other grounds maintenance tools.
• Prune and maintain trees, hedges, and ornamental plantings to promote healthy growth and an attractive campus appearance.
• Apply mulch, fertilizer, and weed control products in accordance with safety guidelines and best horticultural practices.
• Remove leaves, branches, litter, and other debris from campus grounds, walkways, parking areas, and outdoor spaces.
• Perform seasonal landscape maintenance including planting annuals, perennials, and shrubs.
• Assist with snow and ice removal from sidewalks, entrances, parking lots, and other campus areas during winter weather.
• Perform routine inspections, preventative maintenance, and minor repairs on grounds equipment and tools.
• Monitor irrigation systems and report maintenance needs.
• Assist with campus event setup, outdoor projects, and general facilities maintenance as assigned.
• Maintain a safe work environment by following established safety procedures and properly using personal protective equipment.
• Support the Facilities Department with additional duties as assigned.

Required Qualifications And Skills

• High school diploma or equivalent preferred.
• Minimum of one (1) year of professional landscaping, groundskeeping, or related experience preferred.
• Experience operating commercial landscaping equipment and power tools.
• Knowledge of landscape maintenance techniques, including pruning, planting, fertilization, weed control, and seasonal care.
• Basic mechanical aptitude with the ability to perform minor equipment maintenance and repairs.
• Ability to work independently while contributing effectively as part of a collaborative facilities team.
• Strong attention to detail and commitment to maintaining a safe, attractive campus environment.
• Valid driver's license with an acceptable driving record.

Working Conditions

• Work is performed primarily outdoors in varying weather conditions, including heat, cold, rain, snow, humidity, and direct sunlight.
• Regular exposure to dirt, dust, pollen, noise, vibration, grounds maintenance chemicals, and moving mechanical equipment.
• Position may require early mornings, occasional evenings, weekends, overtime, and response to weather‑related emergencies including snow removal, storms, and support for campus events.
• Use of personal protective equipment is required when operating equipment or handling chemicals.

Physical Requirements

• Ability to stand, walk, bend, kneel, squat, climb, and reach for extended periods throughout the workday.
• Ability to frequently lift, carry, push, and pull up to 50 pounds and occasionally move heavier materials with assistance or equipment.
• Ability to safely operate commercial landscaping equipment, power tools, and utility vehicles.
• Ability to perform repetitive physical tasks requiring manual dexterity, hand‑eye coordination, and full range of motion.
• Ability to work safely on uneven terrain, ladders, and slopes.
• Ability to safely perform strenuous physical labor throughout the workday.

Compensation And Benefits

Target hourly range: $24.00-$27.00, commensurate with experience.

Comprehensive Benefits Package, Including

• Health insurance
• Vision insurance
• Dental reimbursement
• Health Reimbursement Arrangement (HRA)
• Employer-paid life insurance
• 403(b) retirement plan with employer contributions
• Professional development opportunities and support

EEO Statement

Westover School is an Equal Opportunity Employer and does not discriminate based on race, color, religion, national origin, ancestry, citizenship status, age, disability, sex, marital status, veteran status, sexual orientation, gender identity or expression, genetic information, or any other characteristic protected by applicable law. We are committed to building a diverse and inclusive community and strongly encourage applications from candidates from historically marginalized or underrepresented backgrounds, as well as those with non-traditional career paths.