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Find an after school nanny in Winchester, MA

After school nannies recommended by families in Winchester. Help with pickup, homework, activities, and more.

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101 experienced after school nannies in Winchester, MA

Families in Winchester use UrbanSitter to find full-time, part-time, and live-in nanny care.
Rates vary by schedule, experience, and responsibilities.

Every after school nanny is background checked annually and their profile is individually reviewed by our Trust & Safety team. Learn more.

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Liv
Booked by 1 repeat family
1 review
$17 per hour for 1 child
Booked by 1 family in Winchester, MA

Looking for a night out? A caregiver for a family member, pet, or child? I’d love to spend some time with them! I’m Liv, I am currently studying Linguistics and Translation in Boston (with an MA drivers license). I have experience in tutoring in Mathematics, English, and French. I have spent many summers babysitting locally and working for my local summer camp. I also have a very long history of elder care, as my father himself is disabled and I used to be his primary caregiver. Additional services: French/English tutoring and immersion, pet sitting, cleaning, errands, Art lessons/activities Additional Skills: French Language and Culture (8+ years), Computer Technology and POS systems, Music (Guitar, Piano, Voice), Dance (7+ years: Jazz, Ballroom, Acro), Visual Art (Painting, Drawing, Sculpture, Printmaking, + more!), Theater, Conflict Resolution, De-escalation, Language Counseling

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Anvi
Booked by 1 repeat family
1 review
$20 per hour for 1 child
Booked by 1 family in Winchester, MA

Hello! My name is Anvi and I am a third year student at Northeastern University. I am from New Jersey and have been a babysitter for the past 6 years. I love to spend time kids doing any indoor and outdoor activities :) I also have my own transportation if needed!

“Anvi was great with my goddaughter. She kept her entertained and Jayla was already asking for her to babysit for her again before the night was over. ”

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Monica 1 review
$20 per hour for 1 child

Hello, my name is Monica I love children, I have experience with infants, toddlers, kindergarten, primary and special education, I love children of all ages and I like to do activities with them like reading, painting,craft, play game, help with homework and teach .

“Monica currently babysits my 8mo daughter 5 days a week while I am at work. When she initially arrived for the in-person interview, I could tell she had not only great experience with kids but is also very empathetic and safety-conscious, which are two very important traits I believe for a person taking care of an infant. She lets me know if she has any concerns and updates me about anything “new” in regards to my daughter . She is also very punctual and dependable; she is very interactive, engaging my daughter with toys, books, music, and conversation. I feel confident when I leave the house in the morning, knowing my daughter is in caring in capable hands. I am so grateful to have found her on Urban Sitters !”

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Gabrielle
Booked by 1 repeat family
2 reviews
$30 per hour for 1 child
Booked by 2 families in Winchester, MA

Hi! My name is Gabby! I have experience caring for children aged 0-12+, I have worked as a camp counselor for a summer and as a day care assistant! I have also worked for 15+ families on babysitting apps and can provide references if needed! I am comfortable with up to four children. I am patient, creative, friendly, and very comfortable enforcing household rules. I enjoy playing outdoor games, board games, and educational games. I have 3 years of college education majoring in social work and minoring in substance use. I have a car! I'm comfortable with all types of pets. I communicate with parents through messages/call updates, always following your preferred method. I am also CPR and First Aid certified. I also have a BT certification. I find joy in watching children learn and grow, and I would love the opportunity to contribute to your family. Please feel free to reach out if you have any questions:)

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Sahra
Booked by 1 repeat family
$20 per hour for 1 child
Booked by 1 family in Winchester, MA

Hello! My name is Sahra. I am a Boston native studying at Northeastern University. I offer child care, pet-care, and household services. I’ve been professionally babysitting for 4 years now. Prior to that I’ve worked at a preschool. I’ve also babysat for family members and family friends practically my whole life. I don’t have my drivers licenses, so picking kids up from school maybe a little difficult, but if the school is walking distance, I can certainly do that! I can also help with homework and tutoring (I currently tutor high school students). I’m also available to cook, clean, and run errands. Pet care - I have a cat of my own, so anything cat care I would love to help out with!

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Recent after school nanny activity in Winchester, MA

After school care starts with trust

Every nanny’s profile is individually reviewed by our Trust & Safety team after an annual background check. Read reviews from families in Winchester to find your fit.

Every nanny on UrbanSitter is background checked annually.

photo of quoted parent Michelle

"Johanna is AMAZING! My two boys love her - she does everything from amazing arts & crafts, to helping with homework, to getting them playing outside! She also drives them and does everything involved with after school activities: packing snacks, getting the right gear, etc."

Michelle R., mom of two

photo of quoted parent Milena

"When we hired Amani, we felt like we hit the jackpot. We were very lucky to find her on UrbanSitter at the beginning of school year. She was picking up kids from school, taking them to afternoon activities, helping them with assignments. She prepped food for them, helped organize their closets and keep their spaces neat and orderly. We would hire her again in a heartbeat."

Milena L., mom of two

photo of quoted parent Heather

"Caitlin has been such a lifesaver for our family. We hired Caitlin to help with the after school routine. The kids took to her instantly. She does it all - school pick ups, dinners, baths, lunch making, clean up, etc. She has really helped make a busy time so much easier for us."

Heather B., mom of two

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Why families use UrbanSitter for after school nannies

Loved by Winchester families

Find after school nannies with reviews from families in your Winchester school, parent group, and neighborhood.

Help with school pickup and activities

Filter for nannies who can drive, then check profiles for carpool, pickup, and activity experience.

Annual background checks

Every nanny clears an annual background check and has their profile reviewed by our Trust and Safety team.

Homework help for school-age kids

Browse profiles to find nannies who can help with reading, spelling, math, projects, and daily homework.

Frequently asked questions about hiring after school nannies in Winchester

How much does an after school nanny cost in Winchester, MA?

After school nanny pay in Winchester is usually hourly and depends on the schedule, the nanny's experience, whether driving is required, and homework help. Most after school roles are part-time, in the range of 15 to 25 hours per week. See current after school nanny costs.

How do I find an after school nanny near me in Winchester?

Sign up for free, post a job with your school-year schedule and needs, then browse profiles with reviews and references from local Winchester families. Message candidates, schedule interviews, and hire when you find the right fit. Learn how UrbanSitter works.

Are after school nannies in Winchester background checked?

Yes. Every nanny in Winchester must clear an annual background check, and each profile is individually reviewed by our Trust and Safety team. See what's included in the background check.

Can my after school nanny drive my kids to activities in Winchester?

Yes. UrbanSitter families in Winchester can specify driving requirements when posting a job, including whether the nanny uses their own car or the family's car. Many after school nannies help with school pickup, driving to activities.

When is the best time to find an after school nanny in Winchester?

Most Winchester families start their search in late summer for an August or September start, matching the school year. Demand peaks in July and August, so families who plan ahead have the widest selection. Mid-year hiring happens too, often when schedules change or families move.

What should I look for when interviewing an after school nanny in Winchester?

Look for experience with your kids' age range, comfort with your school pickup logistics and after-school activities, references from families you trust, and a clear sense of reliability. See interview questions to ask.

Resources

Nanny Interview Questions: A Guide for Parents

Interview questions that surface experience, references, and fit.

How Much Does an After School Nanny Cost

Current rates and what factors affect the price.

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