Houseman / Groundskeeper for Private Estate- Winter Park

Position: Full-Time Groundskeeper (Non-Resident) – Discreet & Experienced

Location: Winter Park, FL
Schedule: Monday–Friday, Full-Time
Compensation: $70,000-$85,000 based on experience, health stipend, and paid time off

Overview:
An ultra-high net worth family seeks an experienced and exceptionally discreet Groundskeeper to maintain the meticulous exterior and landscape of a private estate. This is a non-residential, full-time position requiring the highest standards of care, professionalism, and confidentiality.

Key Responsibilities:

• Hands-on care and maintenance of lawns, gardens, hardscapes, irrigation, and exterior grounds

• Coordination with landscape contractors and seasonal specialists as needed

• Maintenance of outdoor structures, walkways, fences, and related systems

• Monitoring and reporting on the condition of trees, plants, and turf

• Operating and maintaining all landscape-related tools and equipment

• Ensuring exterior areas are clean, organized, and presentation-ready at all times

• Providing discreet support for special events and seasonal preparations

• Observing and respecting household privacy and security protocols at all times

Qualifications:

• Minimum 5 years of experience maintaining high-end or estate-level grounds

• Knowledge of regional flora, irrigation systems, seasonal plant care, and pest control

• Knowledge of Koi pond care a plus

• Strong work ethic and attention to detail

• Demonstrated discretion and experience working with high-profile or private families

• Ability to work independently with integrity and good judgment

• Valid driver's license and reliable transportation

• Background check required

Confidentiality and professionalism are paramount.
This is a trusted role within a private estate setting, and the ideal candidate will approach their work with pride, precision, and respect for the household’s values and privacy.

To apply, please submit a resume and brief cover letter outlining relevant experience and qualification