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Experienced Groundskeeper / Site Manager

Job

Chester Contracting Corp

Dover Plains, NY (In Person)

$52,000 Salary, Full-Time

Posted 1 week ago (Updated 5 days ago) • Actively hiring

Expires 6/18/2026

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Job Description

Job Title:
Experienced Groundskeeper /
Site Manager Location:
Dover Plains, NY Employment Type:
Full-Time /
Year-Round About Us:
We manage multiple properties and facilities and are seeking a reliable Groundskeeper / Site Manager to maintain safe, attractive, and well-kept outdoor spaces. This is a year-round position with responsibilities that change seasonally—grass and landscaping during the warmer months, and snow and ice control in the winter—along with the upkeep of both the interior and exterior of the buildings.
Position Overview:
The Groundskeeper will handle lawn care, tree and shrub maintenance, snow removal, and the general upkeep of outdoor areas. The ideal candidate has experience with landscaping equipment, understands seasonal property needs, and takes pride in keeping the grounds looking their best. In addition, this role includes performing drywall repairs, carpentry work, painting, and other general building maintenance tasks as needed.
Key Responsibilities:
Mow, trim, edge, fertilize, and maintain lawns and open areas Prune trees, trim shrubs, and manage plant health Remove leaves, branches, and other debris Perform snow plowing, shoveling, and salting during winter Operate and maintain landscaping and snow equipment (mowers, trimmers, blowers, plows, etc.) Small repairs indoor and outdoor, painting (drywall, fences, walkways, drainage) Monitor grounds for safety hazards and address issues promptly
Qualifications:
3+ years of groundskeeping or landscaping experience preferred Skilled in operating and maintaining landscaping/snow equipment Ability to operate skid steer, excavator a plus. Ability to work outdoors in all weather conditions Physical ability to lift 50+ lbs and perform manual labor daily Valid driver's license and reliable transportation required Strong work ethic and attention to detail
Compensation & Benefits:
Competitive hourly pay Year-round steady work Paid time off and holidays Apply Today!
Call/Text:
845.832.8224
Email:
management@chesterco.com
Job Type:
Full-time Pay:
From $25.00 per hour
Work Location:
In person

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