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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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Sarah $33 per hour for 1 child

I’ve been a nanny for the past twelve years, with experience ranging from infant to early elementary school aged. I just wrapped up my most recent job as the family’s needs are changing and now I’m looking for work while I figure out what’s next for me. I love keeping kids active and engaged, with plenty of outdoor time as the weather permits. I don’t drive, so I can only take jobs that are MBTA accessible; I’m also experienced and comfortable with taking kids on the t/bus if necessary. Currently, my availability open and pretty flexible, I’m open to one off gigs, temporary jobs, or longer term (1-2 years).

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Wanda
Booked by 37 repeat families
56 reviews
$35 per hour for 1 child
Booked by 66 families in Winchester, MA

Please Note: Holidays Rates: Time and a half for those days Only. I charge for the full amount of hours booked, even if there is an early return. Nicked named "Mary Poppins" by some of my parent's review's. I am warm, caring, and nurturing. I have a strong passion for children, and families. I have a true desire to promote children’s physical, mental, and emotional well-being. I've also spent the last 5 years doing part time Senior care as well. SUMMARY: Over 16 years’ experience in child care. Track record of supervising the activities of children, and assuming the total responsibility of home in absence of parents. I bring a lot to the table. I come with activities to do, Some science experiments, games, books, toys. I'm always trying to find new, and exciting things to do. I am a fun loving, singing dancing, a little silly, playful, friendly person. Who loves to explore the outdoors, going to the Library, Museums, Zoo, and parks. I have a special talent for being calm under pressure. • Neat appearance with a very professional attitude • Legally authorized to work in the United States • Own a reliable vehicle with current Massachusetts driver’s license and insurance Willing to get covid 19 booster. TB tested, Hepatitis, and have been fully vaccinated. Key Accomplishments • Attained 100% satisfaction level for 11 consecutive years based on feedback from clients whose children were placed under my care • Before covid, I created a song to helped children learn to wash their hands for the appropriate time (20 seconds) because, that's so important. • Maintained a secure environment and safeguarded children from many potential hazards • Interacted with children and played games, dance and sing • Organized and monitored children’s recreational and play activities • Updated parents on children progress regularly References upon request

“Wanda was great, punctual and friendly. She brought bubbles and toys with her, and my child had a blast playing with her. Would definitely recommend hiring her!”

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Rachel
Booked by 5 repeat families
7 reviews
$20 per hour for 1 child
Booked by 8 families in Winchester, MA

I have three years of experience working with children between the ages of 5 and 12 through both babysitting and volunteer work. During this time, I’ve gained hands-on knowledge of child safety, communication, and engagement strategies that help create a fun, safe, and supportive environment. I am certified in CPR, First Aid, and AED, which gives me the confidence and skills to handle emergency situations calmly and effectively. I’m naturally outgoing, dependable, and hardworking. I take pride in being consistent and responsible. Whether I’m helping with homework, planning activities, or managing routines, I approach every task with care and attention. In addition to working with children, I’m also open to helping with household tasks or pet care as needed.

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Rashida
Booked by 22 repeat families
14 reviews
$25 per hour for 1 child
Booked by 27 families in Winchester, MA

Hello Families! My name is Rashida and I am a native Bostonian. I am a licensed and experienced Child Care Professional. I have over 20 years of teaching experience and child care experience and I love working with children! I have my Associate's degree in Early Childhood Education and I am infant, toddler, preschool lead teacher qualified and director qualified. I love working with children because I enjoy helping them learn, discover and grow. Seeing and helping infants and toddlers reach new milestones and watching and giving preschoolers and early learners tools to discover the world around them is a joy and is exciting to see. For the past 2 years I have also been teaching Early Childhood trainings and enrichment classes to Educators. The program is in partnership with statewide EEC programs. I am available to provide child care in Boston and in the Greater Boston area. I look forward to meeting and speaking with you!

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Michelle
Booked by 9 repeat families
10 reviews
$27 per hour for 1 child
Booked by 14 families in Winchester, MA

Hello families my name is Michelle I can describe myself as someone patient, honest, creative and very lovely. I started working as a nanny when I was in high school (2013) I have a lot of experience with kids 0-16 years old, I have experience working with multiple kids. At the moment I am a full time nanny of a happy toddler (I started with them when she was 5 months) I am looking for occasional/weekends/evening jobs. I like to prepare activities to engage with the kids accordingly to their age like crafts, painting, dancing, going for walks, visiting the playground, playing sports, board games, puzzles and painting last but not least I’m bilingual so if you want I would be more than happy to teach your kids some Spanish words!! I’m always on time and I work great following schedules/routines. I have an advanced child care training certificate conducted by American Red Cross I love animals so working around pets it’s not a problem at all. I have my own car and clean drive record. I am fully vaccinated and boosted. Thank you, I am looking forward to hearing from you.

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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

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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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