Houseman Position Windermere Estate

Job Title: Houseman

Location: Windermere, FL (Lakefront Estate, 10,000 sq. ft.)

Schedule: Monday–Friday, 9am–5pm, with flexibility for evenings and weekends as needed

Benefits:

• 2 weeks paid vacation (accrued)

• 5 paid holidays

• $300 monthly healthcare stipend

The Houseman is responsible for the upkeep, maintenance, and cleanliness of a 10,000 sq. ft. lakefront estate in Windermere, FL. This hands-on role requires attention to detail, initiative, and a proactive approach to maintaining the property’s three pools, outdoor areas, and overall functionality.

The ideal candidate will work closely with the Estate Manager and other household staff to ensure that the property is maintained to the highest standard and that daily operations run smoothly. This position does not include driving responsibilities or regular travel.

• Perform general maintenance, troubleshooting, and minor household repairs.

• Conduct routine property inspections and promptly report maintenance needs to the Estate Manager.

• Maintain three pools, including cleaning and water quality checks (training provided if necessary).

• Pressure wash patios, walkways, and exterior areas.

• Support seasonal projects, renovations, and vendor coordination.

• Perform routine checks of lighting, HVAC, AV, smart home, and mechanical systems, reporting any issues.

• Ensure all areas of the estate are clean, organized, and in top condition at all times.

• Assist with preparing the home for guests and events.

• Greet and assist vendors or service providers as directed.

• Provide support during in-home gatherings, including setup and breakdown.

• Maintain discretion and professionalism while working in and around the family’s private spaces.

• Assist with indoor and outdoor cleaning and organization.

• Track and restock household supplies and inventory.

• Receive and organize packages and deliveries.

• Monitor property access, maintain logs of vendor visits, and ensure the estate remains secure.

• Experience: 3–5 years in a private estate or luxury hospitality setting.

• Technical
  
  Skills:
  
  Comfortable with household technology and smart home systems.

• Maintenance Knowledge: Basic understanding of home maintenance, repairs, and pool care (training provided if needed).

• Communication: Strong interpersonal and professional communication skills.

• Organization & Detail: Highly organized with a meticulous eye for detail.

• Problem-Solving: Resourceful and able to identify and resolve issues proactively.

• Personal Qualities: Professional, discreet, dependable, and service-oriented.

• Schedule Flexibility: Willingness to adjust schedule for occasional evening or weekend needs.

• Clean Background Check: Due to the nature of the household, all candidates must pass an extensive background check with no exceptions.