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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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Ankita
Booked by 9 repeat families
9 reviews
$30 per hour for 1 child
Booked by 19 families in Winchester, MA

Hello, I am a student pursuing my degree in Northeastern University. I am looking for part time baby sitting jobs. I have some previous experience and I’m really good with children! :)

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Claire
Booked by 2 repeat families
6 reviews
$25 per hour for 1 child
Booked by 9 families in Winchester, MA

Hello! My name is claire and I just moved to the area and I’m looking for some work! I’m 26 and originally from Oregon. I am currently in the BU Physician Assistant Graduate Program. apply for PA school. I graduated from Montana State University in 2022 with a bachelors in science. I have flexibility in my schedule during the afternoons and I’m will do my best to accommodate for your family. I have lots of experience with little kiddos. I have babysat my whole life and nannied kids from the age of 2 to 12. I’ve also coached Soccer for young ones and coached competitive skiing for about four years. This past year I worked at a boarding high school where I lived, cooked, and taught kids from 13 to 17. I taught environmental science and Spanish! I am a nationally certified EMT with my CPR certification. I am really easy-going. I play hands-on with kids and make sure my attention is focused of them. My favorite babysitting gigs is when we can explore their creativity as well as the outdoors! I’d love to do a meet and greet to make sure we’re the right fit for each other!

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Nia
Booked by 4 repeat families
3 reviews
$25 per hour for 1 child
Booked by 6 families in Winchester, MA

Originally from San Francisco, I currently am located Cambridge. I am a patient tutor, care provider, and happy lifelong learner with experience working with various ages and backgrounds. I hold two BAs in Psychology and Sociology, my MS in clinical neuroscience, and am a master's candidate in clinical mental health counseling. I aspire to be a clinical counselor/research scientist in the future. I have provided care for several years during my off time. I have experience working with neurodivergent children/adults (ADHD, autism, etc.), physical and/or mental health conditions and disabilities. I have assisted individuals with learning/communicating utilizing an AAC device. I have also worked with lgbtqia+ children/adults/families. I am passionate about taking time to build genuine connections with folks from all walks of life. I value creating spaces of inclusion, where diversity and accessibility are as important to me as communication and respect.

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Katherine
Booked by 1 repeat family
3 reviews
$35 per hour for 1 child
Booked by 1 family in Winchester, MA

Hi! My name is Katie, I’m a 32-year-old professional nanny with over 10 years of experience caring for newborns, infants, toddlers, and school-age kids. I’m skilled in managing multiples, nanny shares, and children with behavioral, emotional regulation, or executive functioning challenges. My approach emphasizes connection, autonomy, and play-based learning, and I love tailoring activities to each child’s interests, whether that’s singing, dancing, crafting clay figurines, or exploring fun activities around Boston, Cambridge, and the North Shore. I have done many different kinds of jobs including: long-term (3+ years) short-term, overnight, vacations, and date nights! I hold a Child & Youth Advocacy certificate and Associates in Liberal Arts Psychology from NSCC. I am also currently pursuing my Social Work degree at Salem State University. In addition, I volunteer with the Massachusetts Coalition for the Homeless and CASA, bringing a strong commitment to supporting children and families both professionally and in the community. Some of my specific strengths include: • Redirection and emotional coaching • Supporting intuitive eating • Managing ADHD and sensory needs • Creating practical systems that support families long-term Thanks Katie

“Katie is our current nanny to our 2.5-year-old twin girls, and she has been a wonderful addition to our family. One of the things we appreciate most about Katie is her knowledge of child development. She is always coming up with fun, age-appropriate activities that help our girls learn and grow while keeping them engaged and excited. She is also incredibly in tune with children's emotions and does a great job helping our daughters work through big feelings with patience, empathy, and understanding. Katie is dependable, caring, and genuinely invested in our girls' well-being and development. We feel very lucky to have found her and would highly recommend her to any family.”

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

I bring over 10 years of hands-on experience caring for children of all ages, from infants to teenagers. Being that I come from a large family, I naturally stepped into the role of a caregiver early on. Beyond that, I’ve actively cared for my nieces and nephews, building a strong foundation in child care. My experience has taught me patience, adaptability, and the importance of creating a safe, nurturing environment for children to thrive. Whether it’s assisting with homework, planning engaging activities, preparing meals, or maintaining household routines, I take pride in ensuring kids feel supported and valued. I’m also skilled at balancing structure with fun, understanding the unique needs of children at different developmental stages. From soothing infants to mentoring teens, I’ve learned to tailor my approach to each child’s personality and needs. I have a natural ability to connect with people of all ages, which extends to seniors and even pets, having provided companionship and assistance for older family members and cared for household pets. My reliability, strong work ethic, and passion for caregiving make me a great fit for any family seeking a dependable and compassionate helper.

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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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