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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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Heidi Maria $22 per hour for 1 child
Booked by 2 families in Winchester, MA

I’ve been working with kids in all kinds of settings for years, and caring for others has always come naturally to me. I started babysitting at 15, and soon after spent a full year helping out at a daycare with children ranging from 9 months to 8 years old. Since then, I’ve continued to grow my experience in different environments. As well as being the oldest child in my family. For the past five summers, I’ve been a sleep away camp counselor, teaching kids how to sailing and living with kids ages 6 to 14 for up to eight weeks at a time. I’ve also volunteered with preschoolers through Jumpstart for a year, supporting early learning and social development. Right now, I’m a college student doing work‑study at an elementary school, where I assist in both kindergarten and 2nd grade classrooms. These experiences have taught me patience, creativity, responsibility, and how to connect with kids of all ages. Families and employers describe me as dependable, upbeat, and calm under pressure. I’m great with routines, homework help, playtime, and keeping kids engaged. I’m also comfortable with pets and happy to help with light household tasks. And most importantly, I genuinely love what I do. Kids can tell when someone enjoys being around them, and I think that’s what makes the biggest difference.

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Happiness $20 per hour for 1 child

My name is Happiness, mom of 3 kids, 8-4-20 months, finished high school and took college classes in public health, currently pursuing certification in medical assistant. I love kids and taking care of seniors there's that kind of joy I get caring for them. Am very patient and respectful and I dont mind being corrected when am wrong. I love to cook,being neat, make others happy,I try to treat others how I want to be treated and better.Thank you.

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Sabrina $20 per hour for 1 child

I have been working at a daycare for the past four years, gaining hands-on experience in caring for and nurturing children of various ages. In this role, I assist with daily activities such as meal times, playtime, and educational exercises, while ensuring a safe and supportive environment. I collaborate with a team of caregivers to develop age-appropriate learning experiences, encourage social and emotional growth, and maintain open communication with parents. This experience has strengthened my patience, responsibility, and adaptability, while fostering a positive and engaging atmosphere for children’s learning and development.

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Caridad $27 per hour for 1 child

I have been working in childcare since 2017, primarily in center-based environments, where I have held lead teacher positions throughout my career. Working with children has always been something I'm deeply passionate about, and I have experience caring for children of all ages, from infants to school-aged children. In addition to my childcare background, I took some time to expand my professional experience by working as a retail technology manager on Newbury Street in Boston. That role strengthened my leadership, communication, organization, and problem- solving skills, all of which I bring into my work with children and families. After stepping away to enjoy maternity leave with my own baby, I am now looking for a wonderful family to support through babysitting or nannying. Ideally, I'm seeking a position that would allow me to bring my child along two days per week as part of the schedule. I understand the importance of creating a safe, nurturing, engaging, and dependable environment for children, and I strive to build strong, trusting relationships with both kids and parents alike. I am caring, patient, reliable, and experienced, and I truly enjoy helping children learn, grow, and thrive. I am new to this app as of recently I have been on sitter city where I have a 5 star review. I haven't found a long term job so I have decided to move over to urban sitter for a try. Thanks for your time!

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Keila $23 per hour for 1 child

Hi, I’m 25 and currently studying digital and social marketing. I’ve always loved being around kids and animals, and I enjoy reading, organizing, and all things beauty and fashion. Im Responsible, caring, and energetic individual with experience supervising and engaging children in safe, fun, and educational environments. Skilled in managing groups as well. For kids only after school (FKO) Group leader • Provide a positive, safe, fun environment and quality experience to all school-age children and families • Translate and interpret for Social Workers, Site Director, and other administrators with Portuguese-speaking families. • Plan and lead age-appropriate activities, including arts & crafts, games, homework support, and outdoor play. Provide attentive care, including snack preparation, conflict resolution, and emotional support. Communicate effectively with parents/guardians regarding children’s progress, needs, or concerns. Encourage positive social interactions and teamwork among children.

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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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