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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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Arianna $23 per hour for 1 child

Hello!! Im Ari I'm 19 and have been working in childcare for 3 going on 4 years now, I'm the oldest sibling to 3 about to be 4 in June(yay!!) and i'm currently in school for early education and soon to be vet medicine! I am currently working on my license to drive so I will have that soon and I am CPR and First aid certified. I'm at employed at an early education center but hope to making nannying a full time job my favorite age group to look after is infants but I have 3 going on 4 years experience in all age groups infants to school age. I know how to meal prep for all age groups and am good at simple house work like laundry, light housekeeping and dishes.

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medjina $25 per hour for 1 child

Hi! My name is Medjina. I’m a sophomore at Boston College studying Psychology and Human Development, and caring for others has always been something that comes naturally to me. I have experience in both childcare and healthcare. I currently work as a clinical assistant at Dana Farber, and before that I worked at Newton Wellesley Hospital. Those roles have taught me how to be responsible, patient, calm, and attentive, especially in busy or high stress situations. I am used to following routines, prioritizing safety, and communicating clearly with families. I also have a lot of experience working with children. I come from a big family and have spent many years babysitting younger cousins, including toddlers. I’ve always enjoyed being around kids and helping them feel comfortable and supported. I also volunteered as a camp counselor at a local YMCA, where I helped with daily routines, activities, meals, and supervision. That experience helped me learn how to keep kids engaged while also making sure they feel safe and cared for. What I love most about caregiving is building trust and being someone families can rely on. I enjoy creating a calm, positive environment where kids feel secure and parents feel at ease. I’m dependable, organized, and happy to help however I can. I’m comfortable with cooking, cleaning, organizing, household chores, and pet care, and I enjoy helping families keep things running smoothly. I would love the opportunity to support your family and be a sitter you can trust.

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Skyler 1 review
$30 per hour for 1 child
Booked by 2 families in Winchester, MA

Hi there! I’m a 28-year-old caregiver with over 10 years of experience working with children, from newborns to 13 years old, including special needs clients. I specialize in newborn care and am passionate about providing nurturing and attentive support to families. I’m also great with all animals and can help with shopping and cooking. CPR and First Aid certified, I am open to full-time opportunities and look forward to creating a safe and loving environment for your little ones!

“Skyler was on time, connected well with our 8, 7, and 1.5 yr old. She was able to cope with our 1.5 yr old when he was struggling to go to bed. Great personality, bright, and energetic. Definitely recommend!”

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Irma $30 per hour for 1 child

I'm great person I'm mom too I'm helping other's mom's to be able to work or go out .. I'm here to help we the kid's they homework and bring them the park or doctor appointments

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Luisa Fernanda $20 per hour for 1 child

Hello! My name is Luisa. I am a caring, responsible, and patient caregiver with experience supporting children, older adults, and pets. I am passionate about creating a safe, positive, and nurturing environment for every family I work with. I have completed Early Education and Care (EEC) training and hold certifications in CPR, AED, and First Aid. I also have training in adult caregiving and understand the importance of safety, compassion, and effective communication. I enjoy helping children learn and grow through engaging activities, supporting seniors with companionship and daily assistance, and caring for pets with attention and love. Families can count on me to be dependable, trustworthy, organized, and attentive to individual needs. My goal is to provide peace of mind while ensuring that your loved ones receive quality care. I look forward to meeting your family! Highlights • EEC Certified (Early Education and Care) • CPR, AED & First Aid Certified • Adult Caregiving Training • Experience with Children, Seniors, and Pets • Bilingual: Spanish and English

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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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