Job Summary

The Evening Nanny role at 1800 O’Connor Drive is a dynamic, high-responsibility position located in the Parkwoods-Donalda area of North York, Toronto. You will act as the “Evening Anchor” for a 3-year-old and a 9-year-old, bridging the gap between school/daycare and bedtime. This role requires the “wit” to pivot between early childhood play and grade-school homework support, and the “grit” to manage evening transitions, extracurricular transportation, and a late-night schedule with professional reliability.

Job Details

Location: 1800 O’Connor Drive, Toronto, ON (North York).
Pay: $20 – $25 per hour (Based on qualifications).
Status: Part-time, Live-out.
Schedule: Weekdays 5:00 PM – 10:00 PM (or later); potential for extended weekend hours.
The Kids: 3-year-old (Preschooler) and 9-year-old (Grade-schooler).

Key Responsibilities: The “Evening Transition” Cycle

Your primary mission is to maintain a calm, productive, and safe environment during the busiest hours of the family’s day.

Educational Support: Provide focused homework assistance to the 9-year-old, ensuring school assignments are completed accurately before the “wind-down” begins.
Developmental Play: Engage the 3-year-old in age-appropriate activities that promote fine motor skills and creative expression, keeping them occupied while the older sibling studies.
Safe Logistics: Drive the children to evening extracurriculars (sports, music, or tutoring), requiring a high level of road safety and punctuality.
Bedtime Routine: Facilitate a smooth transition to sleep, including light meal/snack prep, tidying up play areas, and following established hygiene routines.
Extended Coverage: Maintain a professional demeanor during late-night hours, providing the parents with peace of mind during their evening commitments.

Candidate Profile & Qualifications

The “Multi-Stage” Expert: Proven ability to engage two children at vastly different developmental levels simultaneously.
Academic Wit: Competency in elementary-level subjects to provide effective homework guidance for a 4th-grade curriculum.
Operational Grit: Reliability for a 10:00 PM finish; this role is ideal for those who thrive in evening shifts.
Licensed Driver: A valid driver’s license and a clean driving record are essential for the transportation component of the role.
Character: A friendly, caring demeanor that aligns with a family-oriented value system.

Technical Insights: The “Split-Attention” Strategy

Caring for a 3-year-old and a 9-year-old during the “witching hour” (5 PM – 8 PM) requires strategic time management.

Zone Management: You will likely implement “One-on-One Rotations.” For example, the 3-year-old engages in supervised sensory play (e.g., kinetic sand or puzzles) while you sit with the 9-year-old for 20 minutes of intensive math or reading support.
The “Wind-Down” Hierarchy: Evening care is about lowering the household’s “cortisol levels.” You move from high-energy activities (park/driving) to medium-energy (homework/dinner) to low-energy (reading/bedtime).
Safe Transit Protocols: When driving two children of different ages, you must be proficient in multi-stage car seat/booster seat safety requirements according to Ontario Ministry of Transportation guidelines.

Why Join This Toronto Family?

The O’Connor Drive area offers a central North York location with easy access to transit and local amenities.

Consistent Evening Income: This role provides a stable block of 25+ hours per week, making it a perfect “anchor” job for students or professionals with morning commitments.
Competitive Rate: At $20–$25/hour, this position recognizes the added responsibility of homework help and driving duties.
Professional Trust: High-late-night roles often lead to long-term “household favorite” status, providing job security and a strong personal reference.
Work-Life Balance: If you prefer to have your mornings and early afternoons free for personal projects or education, this 5 PM start is an ideal fit.

Job Description

Do you believe that the hours between 5 PM and 10 PM are the most critical for a child’s sense of security and success? A Family at 1800 O’Connor Drive is seeking an Evening Nanny. We aren’t looking for a “passive sitter”; we are looking for an engaging mentor who has the “grit” to manage a late-night schedule and the “wit” to help a 9-year-old master their math while keeping a 3-year-old entertained. If you are a reliable driver and a caring educator, you belong here.

In this role, you are a “Routine Architect.” You understand that a successful evening sets the tone for the next school day. Your goal is to provide “Excellence in Evening Care,” ensuring the transition from play to homework to sleep is seamless. We look for “Reliable-first” individuals who are professional, fun-loving, and ready to become a valued part of the household.

Joining this family means providing them with the freedom to work or travel, knowing their children are in expert hands. We offer a respectful work environment and a competitive hourly rate for your expertise. If you are a nanny with a commitment to “Academic Support and Child Safety,” we invite you to reach out and meet the family today.

1800 O’Connor Drive: A Hub for Seniors’ Care Excellence

1800 O’Connor Drive is a prominent long-term care campus in the Victoria Village neighborhood of North York, Toronto. It is home to two distinct care communities operated by Sienna Senior Living, one of Canada’s largest owners and operators of seniors’ living providers. The site is defined by a culture of compassion, clinical excellence, and resident-centered living.

In 2026, this address serves as a critical healthcare pillar for the East York and North York communities:

1. Fountain View Care Community

Fountain View is a 158-bed long-term care home that provides a high level of support for residents with complex care needs.

The “Circle of Care” Approach: The culture is built on a multidisciplinary team model where nurses, PSWs, dietitians, and physiotherapists collaborate daily to ensure “whole-person” wellness.
Specialized Dementia Units: The facility features secure units designed specifically for those living with Alzheimer’s and related dementias, focusing on safety without sacrificing a sense of “home.”
Amenities: Residents have access to an on-site hair salon, barber services, dental and foot care clinics, and a vibrant calendar of social and recreational programs.

2. Harmony Hills Care Community

Sharing the same campus, Harmony Hills is a 160-bed licensed long-term care home known for its “themed neighborhoods” and cozy, residential atmosphere.

Themed Neighborhoods: The interior is uniquely designed with vibrant murals and décor that help residents navigate the space and foster a sense of individuality and belonging.
Holistic Programming: The culture at Harmony Hills emphasizes personal interests, offering programs in music, art, and horticulture to keep residents engaged and active.
Spiritual Support: The facility includes a multi-faith chapel, catering to the diverse spiritual backgrounds of Toronto’s senior population.

3. Integrated Services & 2026 Operations

Both communities at 1800 O’Connor Drive operate under a shared mission of “putting residents first” and utilize integrated resources to maximize efficiency and care quality:

Professional Standards: In 2026, the campus maintains a rigorous “Infection Prevention & Control” (IPAC) standard, led by dedicated site leads to ensure resident safety in a post-pandemic landscape.
Waitlist Dynamics: As of January 2026, Harmony Hills reported a waitlist of approximately 473 people, reflecting the high demand for quality long-term care in the Toronto Central area.
Technological Integration: The campus utilizes digital health records and automated medication management to reduce administrative load and allow staff more direct interaction time with residents.

4. Workplace Culture & Opportunities

For healthcare professionals (RNs, RPNs, PSWs, and Allied Health), 1800 O’Connor Drive offers a performance-driven yet empathetic work environment.

Learning & Development: Sienna Senior Living provides extensive “Sienna University” training modules, focusing on specialized geriatric care and leadership development.
Salary & Stability: Being part of a large corporate operator provides employees with stable benefits, pension options, and clear career ladders within the broader network of Ontario seniors’ living.

Living or working at 1800 O’Connor Drive means being part of a “Life-Enriching Community.” Whether it is the dedicated “Angels of Mercy” at Fountain View or the recreation teams at Harmony Hills, the experience is defined by a deep commitment to dignity, respect, and the joy of daily living for Toronto’s seniors.

To apply for this job please visit www.siennaliving.ca.