Find & Apply For Nanny / Babysitter Jobs in Winchester, Massachusetts

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Home Work Staffing

Part-Time Driving Nanny

Pay: $28–$32/hr

Posted: 5 days ago

Location: Winchester, MA (Onsite)

Last Updated: 15 hours ago

Hours: Part-Time

Expires: 10/12/2026

Job Description

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. 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 Upon submitting this form, you will be considered for any suitable positions, so there is no need to complete multiple applications.