Residential Property Caretaker Team

Tapestry Associates   Orcas , WA   Full-time     Hospitality
Posted on November 18, 2021

Private Estate - Orcas Island, WA
Private Employer


A private couple seeks an energetic, experienced, proactive, and hands-on team to support an approximately 15-acre estate on Orcas Island, located in the beautiful San Juan Islands of Washington State. The team will ensure smooth operations, clear and consistent communication, and respond promptly to family requests. The residence serves as a vacation home with the family in residence some of June and nearly all of July and August. The 3-level main residence is approximately 6,000 sq ft, and a separate 2-level guest house is approximately 4,000 sq ft. The property features a separate 3-car garage and bunkhouse, outdoor pool, tennis, and pickleball courts. The grounds include fenced cutting and vegetable gardens, large lawn areas, saltwater shoreline, and a 100’ wooden floating dock. The family moors several boats and maintains kayaks and paddleboards. The family enjoys a busy, active family environment and frequently hosts their family, friends, and friendly dogs on extended seasonal family visits, particularly during the peak season months of June - September. Out-of-state travel is not required though local driving and occasional provisioning trips to the Anacortes area will be expected.

The housekeeper/culinary support role will oversee detailed housekeeping, laundry, pantry, and kitchen organizing, errand and grocery running, supply shopping, and assistance with preparation, serving, and clean-up following family meals. The handyman/caretaker will oversee routine preventative maintenance and corrective repairs to the buildings, equipment, vehicles, vessels, and grounds. Both positions will interface pleasantly with service providers, aid with interior/exterior cleaning and ad hoc project requests. Service-mindedness, flexibility, and a positive attitude are critical, as is a willingness to provide service in a respectful, courteous, and politely informal manner.

The ideal team will have 5+ years of experience in a similar domestic couple/caretaker position in the San Juan Islands or other island locations and demonstrated experience living in a remote, non-urban environment. The family seeks a long-term placement.

Accommodations: A furnished three-bedroom two bath, 1689 sq ft home located one mile from the property is provided for a reduced rental fee of $500 per month. This nicely maintained home and property includes a post and beam barn on a fully fenced one-acre lot with various perennial and edible garden spaces and fruit trees. Pets ok. Candidates should be legally able to drive and have their own reliable transportation (work-related mileage will be reimbursed).


  • Housekeeping/culinary support
    • Oversee and direct weekly part-time detailed housekeeping services, including dusting, polishing, vacuuming, household organization, and other assigned tasks. The family enjoys the support of a longstanding part-time housekeeper who will serve as a partner in providing housekeeping support. A willingness to step in and provide hands-on support during peak periods is required.
    • Provide laundering of washable and delicate clothing and laundering, ironing,  dry cleaning, and storage of linens. Sewing, mending, and steaming skills are a plus.
    • Monitor household inventories to ensure all household products are stocked as required and that supplies, toiletries, cabinets, pantries, and closets are well organized.
    • Errand running, grocery shopping/restocking, and monitoring of product expiration dates.
    • When the family and/or guests are in residence, this role will assist with the daily preparation of healthy family-style meals with nice presentation and service skills. The role will support family gatherings (of 6 – 20) as the family often enjoys cooking when together. Photos of examples of family-style food preparations and menus are welcomed!
    • Preparation of household manuals documenting Owner preferences and standard operating procedures.
    • Frequent support of extended family visits, including adults, children, and their friendly & playful dogs.
  • Handyman/Caretaker Support
    • Troubleshooting and conducting light maintenance and handyman tasks to ensure consistent preventative maintenance of interior residence and exterior facilities.
    • Review and coordinate with the family on tasks requiring support by outsider vendors or service providers (i.e., landscaping, pool maintenance, plumbing, electrical, etc.)
    • Perform regular inspection of the home's interior/exterior to ensure all systems, facilities, and appliances are in good working order.
    • Will be responsible for monitoring the proper function of the security system and providing general property risk assessment (i.e., fencing, or exterior gate malfunction, exterior motion detector, and lighting malfunction, post-storm walkthroughs, leak identification & detection, etc.
    • Completing daily tasks such as general cleaning, trash removal, snow removal, interior window washing, and small equipment maintenance.
    • Ensure family vehicles are maintained and serviced, cleaned, and fueled with insurance and registration up to date.
    • As required, collect receipts from vendors, verify against work performed, and then present to the family for their review and approval.
    • Alert Owners promptly to issues requiring their immediate attention and prepare monthly property and project reports that summarize project status and property conditions.
    • Experience supporting and operating marine vessels and providing related watercraft and water activity support is a plus.
    • Preparation of property and facilities maintenance manuals documenting Owner preferences and standard operating procedures.


  • Demonstrated experience in maintaining the confidentiality, safety, security, and privacy of their employer.
  • Ability to work closely with family members and service providers to promote a productive congenial environment. Should possess a hands-on, "no job too big or too small" attitude.
  • Service-oriented, friendly but not overly familiar, have an intuitive sense of maintaining appropriate boundaries and providing Family privacy while simultaneously providing close-in daily support.
  • Resourceful, dependable, and exhibit good judgment, able to maintain grace under pressure.
  • Enjoy supporting frequent busy, bustling extended family visits with young children and pets in attendance.


  • 5+ years experience working in a similar capacity, with excellent references from past employers.
  • Must be very familiar with the San Juans and/or Washington State area. Prefer current WA state residents or those that have lived in WA in the past – experience working on Orcas Island would be ideal. Must enjoy living in rural, non-urban settings.
  • Must be energetic, physically fit, have a great work ethic, be flexible, and possess a can-do attitude.
  • Strong communication skills, both written and verbal, fluency in English.
  • Candidates must complete both Federal and State background checks and hold US work authorization.
  • Valid driver's license with a clean driving record required.
  • No cigarette smoking is allowed on the family property or inside the Caretaker residence.


  • Offering a salary of $85,000 DOE, annual bonus opportunity, 15 days paid-time-off (during non-peak season periods), and housing provided at a monthly rental price of $500 per month. No health insurance provided.
  • The schedule is Monday - Friday during the off-season and Tuesday – Sunday when the family is in residence with occasional evenings. Flexibility to modify days off will occasionally be required.
  • The team is expected to be fully vaccinated and will follow CDC Guidelines, including social distancing, mask-wearing & hand washing recommendations. Pre-employment COVID-19 testing is required, and the family may request occasional retesting as/if situations warrant. 

Please apply at link: or email resume to