Part-Time Driving Nanny

Home Work Staffing; Winchester (MA); On-site; USD 39,000 - 44,000; Part time

Benefits offered by this job

1 week of paid vacation

2 paid personal days

3 paid holidays

Family vehicle provided for working

2 paid sick days

Job summary

Home Work Staffing is seeking a dependable Part-time Driving Nanny in Winchester, MA to care for two school-age girls (ages 5 and 8) on weekday afternoons. Driving is the core function, with a short walk to the bus stop and daily transportation to activities. A Great Dane is in residence, so comfort around large dogs is essential.

Start late September with a long-term, live-out arrangement. The family provides a vehicle for work-related driving, and the schedule is Monday–Thursday, 2:15 PM –

Qualifications

• Prior professional childcare experience with school-age children.
• Valid driver’s license and confidence behind the wheel.
• Reliable transportation to Winchester, MA.
• Comfortable around a large dog (Great Dane).

Responsibilities

• Walk to bus stop to meet the girls after school.
• Drive the girls to and from activities using the family vehicle.
• Supervise and engage the children during afternoon hours.
• Assist with homework as appropriate for age.
• Bath time for both girls prior to dinner.
• Light tidying related to the children.

Skills

Driving

Reliability

Punctuality

Childcare

Job description

Part‑Time Driving Nanny (Winchester, MA)

Location: Winchester, MA
Compensation: $28–$32 per hour
Commitment Level: Part‑time, live‑out, long‑term
Guaranteed Hours: 16 hours per week
Schedule: Monday–Thursday, 2:15 PM – 6:15 PM
Start Date: Late September / first week of October

Position Overview

A warm, active Winchester family is seeking a dependable long‑term nanny to provide weekday afternoon care for their two daughters, ages 5 and 8. Driving is the heart of this role — both girls have full activity schedules, and the nanny will serve as their afternoon transportation to and from commitments around town. The day begins with a short walk to meet the girls at the bus stop three minutes from the house, followed by activity runs, downtime at home, and evening routine. The family provides a vehicle for all child‑related driving, with parking available at the residence. The household includes a Great Dane, so comfort and confidence around large dogs is essential.

Benefits:

• 1 week of paid vacation
• 2 paid personal days
• 3 paid holidays
• Family vehicle provided for working
• 2 paid sick days

Responsibilities

• Walk to the neighborhood bus stop (approximately three minutes from the home) to meet both girls at dismissal
• Drive the girls to and from after‑school activities using the family vehicle — this is the central function of the role
• Supervise and engage the children during afternoon hours
• Assist with homework as age‑appropriate
• Bath time for both girls prior to dinner
• Light tidying related to the children (toys, backpacks, activity gear)
• Maintain a calm, safe presence in a household with a large dog

Requirements

• Prior professional childcare experience with school‑age children
• Valid driver's license, and genuine confidence behind the wheel
• Reliable personal transportation to and from the family's home in Winchester
• Comfortable and confident around large dogs (Great Dane in residence)
• Reliable and punctual — the schedule depends on precise bus‑stop and activity timing
• Seeking a long‑term commitment
• Must be able to provide 3–5 professional references