Babysitting and Nanny Jobs in Windemere MA

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Found 96 babysitting and nanny jobs within 50mi of Windemere MA 2045. Showing 49 to 72. Sorted by

Flexible Afternoon Care for Independent Teen

Marblehead, MA | 13 mi

Start Date: 13 Dec 25
Applications Close: 13 Dec 25

Posted by Court 12 days ago

Job Details: Casual Babysitting

$27 per hour

Do you enjoy working with independent teens and have reliable transportation? We're seeking a responsible caregiver for our self-sufficient high school freshman. Key Details: • Age Group: High School Student (Freshman) • Hours: As-needed, flexible scheduling • Start Date: December 13, 2025 What We Need: • Must have personal vehicle for transportation • Provide supervision and light support • Help with occasional homework • Ensure student's safety during after-school hours Responsibilities: • Transportation assistance • Homework supervision • Light housekeeping • Maintaining a safe, supportive environment Compensation: • $25-$29 per hour • Flexible start time Perfect for a reliable, responsible caregiver who enjoys working with independent teens and can provide transportation. References required.

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Afternoon Fun with School-Age Child in Brookline

Brookline, MA | 13 mi

Start Date: 19 Nov 25
Applications Close: 19 Dec 25

Posted 20 days ago

Job Details: Part-time

$15 per hour

Are you a reliable and engaging after-school companion? We're seeking a caring babysitter for our awesome 6-11 year old!

Job Details:
• Days: Tuesday, Wednesday, Thursday, Friday
• Hours: 2:30 PM - 6:30 PM
• Location: Brookline, MA
• Hourly Rate: $15/hour

Responsibilities:
• Provide safe, fun supervision after school
• Help with homework if needed
• Engage in age-appropriate activities
• Ensure child's comfort and safety

Start Date: November 19th

Ideal candidate is patient, energetic, and enjoys spending time with elementary-age children. Come make a difference in a young learner's day!

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NEW! Playful Toddler Needs Fun & Caring Sitter

Melrose, MA | 14 mi

Start Date: 06 Dec 25
Applications Close: 13 Dec 25

Posted by Billy 36 minutes ago

Job Details: Casual Babysitting

$27 per hour

Exciting opportunity for a warm, attentive caregiver to join our family! We're seeking a trustworthy babysitter for our energetic toddler, starting December 6th with flexible hours. Key Responsibilities: • Engage our child with fun, interactive activities • Ensure a safe, nurturing environment • Prepare healthy meals • Maintain tidy play areas with light cleaning • Follow our established family routines • Provide regular, open communication What We're Looking For: • Patience and genuine warmth with children • Ability to guide and play creatively • Reliable and communicative personality Compensation: $25-$29 per hour for the right candidate Looking forward to meeting a caring sitter who can bring joy and structure to our little one's day!

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NEW! Fun Holiday Toddler Care - Medford Winter Break

Medford, MA | 14 mi

Start Date: 26 Dec 25
Applications Close: 24 Dec 25

Posted by Nadia 36 minutes ago

Job Details: Casual Babysitting

$25 per hour

Are you a nurturing and energetic caregiver looking for a rewarding short-term opportunity? We need a skilled babysitter for our adorable toddler during the winter daycare break!

Job Details:
• Dates: 6 weekdays between Dec 26th and Jan 1st 2026
• Hours: 9:00 AM to 5:00 PM
• Location: Medford, MA

What We're Looking For:
• Experience with toddlers
• Ability to engage in age-appropriate learning activities
• Enthusiastic and reliable personality
• Recent local references required

Responsibilities:
• Plan and lead fun, educational activities
• Prepare healthy meals and snacks
• Perform light child-related housekeeping

Compensation:
• $20-$30 per hour
• Potential for continued occasional sitting in the new year

Ideal candidates will bring creativity, patience, and a genuine love for working with young children!

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Sweet Baby Care in Medford - Weekday Mornings

Medford, MA | 14 mi

Start Date: 01 Dec 25
Applications Close: 11 Dec 25

Posted 7 days ago

Job Details: Part-time

$15 per hour

Are you a caring, dog-friendly babysitter looking for a rewarding part-time opportunity? We have an adorable 6-month-old baby who needs loving care in our Medford home! 🕒 Schedule: Monday-Thursday, 9am-3pm 💰 Competitive Pay: $15-50 per hour 🐶 Must be comfortable around dogs 🚗 Reliable transportation required 🚭 Non-smokers only Job starts December 1st. We're seeking a warm, responsible caregiver who can provide gentle, attentive care to our little one during weekday mornings. Ideal candidate will be patient, energetic, and love spending time with infants. If you're looking for a consistent, positive babysitting opportunity, we want to meet you!

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Growing Family Needs Caring Sitter

Melrose, MA | 14 mi

Start Date: 31 Dec 25
Applications Close: 14 Jan 26

Posted 7 days ago

Job Details: Part-time

$20 per hour

Exciting opportunity to support a family through a special transition! We're seeking a nurturing part-time babysitter to help with our 2-year-old son during a meaningful family period. Job Details: • Schedule: Tuesdays, Thursdays, and Fridays from 9am-12pm • Starting January 1st • $20/hour • Currently helping mom prepare for maternity leave • Will transition to supporting both a toddler and newborn Ideal Candidate: • Experience with children ages 0-6 years • Comfortable with family dynamics during a big transition • Reliable and patient • Non-smoker with own transportation Long-Term Potential: This role offers the opportunity to grow with our family beyond the initial maternity leave period. We're looking for someone who can build a lasting connection with our children. Our goal is finding a compassionate caregiver who can help our 2-year-old feel secure and supported as he becomes a big brother!

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Fun Toddler Care - Medford Tues/Thurs Nights

Medford, MA | 14 mi

Start Date: 15 Nov 25
Applications Close: 07 Dec 25

Posted by Anna a month ago

Job Details: Part-time

$26 per hour

Looking for a caring and energetic babysitter to join our family!

We need a reliable caregiver for our delightful toddler with these key details:

• Days: Every Tuesday and Thursday
• Time: 5:30 PM - 8:00 PM
• Location: Medford, MA
• Pay: $25-$27 per hour

Your exciting responsibilities will include:
• Engaging our child in fun, age-appropriate activities
• Preparing healthy snacks
• Supporting bedtime routine
• Light housekeeping
• Assist with toilet training

Ideal candidates have:
• Experience with toddlers
• Punctuality
• Warm, nurturing personality
• Ability to create a safe, playful environment

We're flexible on start date and eager to find the perfect match for our little one. If you love spending time with toddlers and can provide attentive, loving care, we want to hear from you!

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NEW! Teen Transport & After-School Companion

Dedham, MA | 15 mi

Start Date: 05 Dec 25
Applications Close: 19 Dec 25

Posted 36 minutes ago

Job Details: Part-time

$27.5 per hour

Exciting Opportunity for a Reliable Driver in Dedham! 🚗

We're seeking a dependable transportation professional to support a high school student's daily routine. Your key responsibilities include:

• Picking up student from school in Jamaica Plain
• Driving to after-school activities
• Occasional sibling pick-ups and errands

Job Details:
• Location: Dedham, MA
• Daily Schedule: 3:30pm - 5:30pm (Flexible)
• Compensation: $25-$30 per hour

Required Qualifications:
• Excellent driving record
• Reliable personal vehicle
• Punctual and responsible

This is more than just driving - you'll be a trusted support for a local high school student's daily journey. Perfect for responsible drivers who enjoy working with teens!

Interested candidates, let's connect and discuss this exciting opportunity!

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NEW! Fun Weekend Kids Care in Belmont

Belmont, MA | 16 mi

Start Date: 06 Dec 25
Applications Close: 28 Dec 25

Posted by Grant 36 minutes ago

Job Details: Casual Babysitting

$25 per hour

Looking for a rockstar babysitter to join our family for weekend adventures! 🌟

We have two awesome kiddos - a curious 1.5-year-old and an energetic almost-5-year-old who love engaging activities and playtime.

Job Highlights:
• Occasional weekend afternoons (typically 3-hour blocks)
• Competitive pay: $25-$26 per hour
• Start date: December 2025

What We Need:
• Experience watching multiple children
• Reliable and punctual attitude
• Passion for creating fun, safe play experiences
• Ability to prepare simple snacks

Bonus Points:
• Background check comfort (may be required)
• Creative activity planning skills
• Warm, nurturing personality

If you love spending time with little ones and can commit to a flexible weekend schedule, we want to hear from you! Let's create some magical memories together. 👧👦

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NEW! Active 2nd Grader Needs Afternoon Companion

Arlington, MA | 16 mi

Start Date: 16 Nov 25
Applications Close: 16 Dec 25

Posted an hour ago

Job Details: Part-time

$27 per hour

Exciting Opportunity for a Fun, Responsible Caregiver! We're seeking an energetic babysitter to support our 7-year-old son after school in Arlington, MA. This is more than just a babysitting job - it's a chance to make a real difference in a child's day! Job Highlights: • Competitive Pay: $25-28 per hour • Flexible Start Date: Beginning November 17th • Consistent Schedule: Mon/Tue/Thu/Fri 2:30-5:30 PM, Wed 1-5:30 PM Key Requirements: • Must have reliable car and clean driving record • Excellent English communication skills • Comfortable with our playful 5-month-old puppy • Ability to provide structured yet fun environment Responsibilities: • Pick up from school • Drive to after-school activities (3 days per week) • Engage and supervise 2nd-grade boy • Maintain a positive, active atmosphere Bonus Benefits: • Paid holidays • Guaranteed minimum hours • Sick and vacation time • Mileage reimbursement Ready to be an awesome after-school companion? Let's connect!

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NEW! Nurturing Half-Day Nanny for Happy Baby Girl

Newton, MA | 16 mi

Start Date: 12 Jan 26
Applications Close: 05 Jan 26

Posted an hour ago

Job Details: Part-time

$30 per hour

Calling all loving, experienced nannies! 👶 We're a warm Newton family seeking a dedicated caregiver for our playful 7-month-old daughter. Job Highlights: • Part-time hours: Monday-Friday, 12pm-5pm • Competitive pay: $25-30 per hour • Start date: January 12th, 2026 What We Need: • Consistent, nurturing care • Help with feeding and nap schedules • Interactive play and developmental engagement • Excellent communication skills Ideal Candidate: • Non-smoker • Own transportation • Comfortable around pets • Passionate about infant care Your Responsibilities: • Prepare bottles and solid foods • Diaper changes and baby hygiene • Ensure baby's safety • Build a trusting relationship with our family This is more than a job - it's a chance to be part of our daughter's early development journey! Experienced, reliable nannies: We can't wait to meet you! 💕

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Loving Newton Family Seeks Half-Day Infant Nanny

Newton, MA | 16 mi

Start Date: 12 Jan 26
Applications Close: 05 Jan 26

Posted 12 days ago

Job Details: Part-time

$30 per hour

Adorable 7-month-old daughter needs a nurturing nanny for fun afternoons! Perfect for the right candidate who loves engaging with curious babies and building a long-term connection. 📍 Location: Newton, MA ⏰ Schedule: Monday–Friday, 12:00PM–5:00 PM 💰 Pay: $25-35/hour based on experience Responsibilities: • Maintain consistent nap and feeding schedule • Prepare bottles and solid foods • Diaper changes and baby hygiene • Interactive developmental playtime • Ensure baby's safety and happiness What We're Looking For: • Experienced and reliable • Loves working with infants • Excellent communication skills • Non-smoker • Has own transportation • Comfortable around pets Start Date: January 12, 2026 Join our family and make a difference in a little one's life!

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Playful After-School Sitter in Arlington Center

Arlington, MA | 16 mi

Start Date: 15 Dec 25
Applications Close: 15 Dec 25

Posted 12 days ago

Job Details: Part-time

$25 per hour

Looking for a warm-hearted childcare pro to join our family! We need a fantastic sitter for our two adorable kiddos (ages 2 and 4) three afternoons per week. 📍 Location: Arlington Center, MA ⏰ Hours: Monday, Tuesday, Wednesday from 3-5pm 💰 Pay: Competitive $25/hour (flexible for right candidate) Your awesome responsibilities: • Welcome kids after school • Help with hand washing • Prepare healthy snacks • Engage in fun, age-appropriate play • Create a nurturing afternoon environment What we're looking for: 1. Proven experience with young children 2. Flexible, reliable schedule 3. Positive, energetic personality Bonus points if you: • Share a bit about your childcare background • Explain why this schedule works for you • Have a sense of humor (PS: Tell us your favorite color! 🌈) Our current sitter is heading abroad, so we're seeking someone special to continue the magic!

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Playful Toddler Buddy Needed - Flexible Hours!

Wakefield, MA | 16 mi

Start Date: 10 Dec 25
Applications Close: 10 Dec 25

Posted by Anusha 12 days ago

Job Details: Casual Babysitting

$24 per hour

Are you an energetic, patient caregiver who loves spending time with little ones? We're looking for an amazing babysitter for our vibrant toddler!

Job Details:
• Start Date: December 11, 2025 (Flexible scheduling)
• Compensation: $19 - $29 per hour
• One adorable toddler to care for

Responsibilities:
• Engage in age-appropriate play activities
• Prepare nutritious snacks
• Support nap time routines
• Create a safe, fun learning environment

Ideal Candidate:
• Previous experience with toddlers
• High energy and attentive nature
• Comfortable with flexible, as-needed schedule

If you're passionate about child development and enjoy making learning fun, we want to hear from you! Let's create memorable moments together.

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Fun Family Night Care - 2 Kids in Arlington

Arlington, MA | 16 mi

Start Date: 24 Nov 25
Applications Close: 18 Dec 25

Posted by Michael 12 days ago

Job Details: Casual Babysitting

$27.5 per hour

Exciting Occasional Babysitting Opportunity! 🌟

We're seeking an amazing sitter for our two energetic children - a curious 15-month-old and a playful 4-year-old preschooler in Arlington, MA.

Job Highlights:
• Competitive Pay: $25-$30 per hour 💰
• First Need: 11/24 evening for a few hours
• Supervise daily activities & playtime
• Prepare delightful snacks
• Create a safe, engaging learning environment

Ideal Candidate:
• Experienced with multiple children
• Valid driver's license preferred
• Comfortable walking/transportation near bus stop

What We Value:
• Patience & creativity with kids
• Ability to manage both a toddler and preschooler
• Genuine love for child development

interested in joining our family's occasional care team? Let's connect and make some magical memories! 👨‍👩‍👧‍👦

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Early Morning Family Helpers Needed!

Arlington, MA | 16 mi

Start Date: 05 Jan 26
Applications Close: 18 Dec 25

Posted by Costanza 12 days ago

Job Details: Part-time

$27 per hour

Are you a morning superhero who loves kids? We need a reliable morning companion for our three wonderful children! Job Details: • Ages: Preschool and Elementary School • Days: Monday - Friday • Hours: 7:00 AM - 10:00 AM • Start Date: January 5, 2026 Your Mission: • Help kids get dressed and ready for school • Prepare and serve breakfast • Provide safe, fun morning transportation • Light housekeeping and laundry What We Need: • Comfortable driving children • Experience with multiple kids • Must have reliable transportation • Warm, engaging personality Compensation: • $25 - $29 per hour • Consistent weekly schedule If you're energetic, responsible, and love creating positive morning experiences for kids, we want to meet you! Professional, experienced childcare providers preferred.

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Fun Arlington Family Seeks Caring Nanny PT

Arlington, MA | 16 mi

Start Date: 02 Feb 25
Applications Close: 15 Dec 25

Posted 20 days ago

Job Details: Part-time

$30 per hour

Are you a nurturing, creative professional looking for a rewarding part-time childcare opportunity? We have an exciting position for a passionate caregiver! We're seeking a warm, energetic nanny to join our family in Arlington, caring for three wonderful children: • Baby girl (5 months in February) • Two active boys (ages 3 and 4) Job Highlights: • Competitive Pay: $25-35/hour • Flexible Schedule: Mondays and Fridays (8am-5pm and 8am-12:30pm) • Guaranteed 14 hours/week with potential for extra evening shifts Your Ideal Profile: • CPR Certified • College Degree preferred • Non-smoker • Comfortable with pets • Strong communication skills • Safety-focused and family-oriented Daily Responsibilities: • Morning baby care • Preschool pickups for boys • Engaging, creative interactions • Light child-related tasks Car provided with 3 car seat hookups during work hours. Start date: February 2nd. Are you the perfect fit for our family?

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Fun Toddler Care - Flexible Hours in Marshfield

Marshfield, MA | 16 mi

Start Date: 15 Nov 25
Applications Close: 15 Dec 25

Posted by Ryan 20 days ago

Job Details: Casual Babysitting

$27 per hour

Exciting opportunity to engage with an adorable 13-month-old explorer in Marshfield! We're seeking a warm, reliable babysitter for occasional care of our curious toddler. Key Responsibilities: • Play and learning activities • Meal preparation • Bedtime routine • Ensuring a safe, nurturing environment What We Need: • Comfortable with active toddlers • Effective communication skills • Reliable transportation • Flexibility for as-needed care Compensation: • $25-$29 per hour • Start Date: November 15, 2025 Our daughter loves to babble and discover her world. If you're patient, energetic, and love supporting a child's growth, we want to meet you!

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NEW! Playful Preschooler Needs Caring Companion

Beverly, MA | 18 mi

Start Date: 12 Dec 25
Applications Close: 12 Dec 25

Posted by Sarah 36 minutes ago

Job Details: Casual Babysitting

$24 per hour

Exciting opportunity for a fun and responsible caregiver to join our family! We're seeking a reliable babysitter for our delightful preschool-aged child who loves adventure and learning. Key Details: • Start Date: December 12, 2025 at 9:00am • Hourly Rate: $24 - $28 per hour • Occasional/Flexible Schedule Responsibilities: • Supervise engaging playtime • Prepare healthy snacks • Manage smooth nap times • Ensure child's safety and happiness Must-Haves: • Reliable personal transportation • Comfortable around friendly cats • Punctual and energetic personality • Great at connecting with young children Our home is pet-friendly with two laid-back cats who will be nearby during your time with us. Looking for a warm, attentive caregiver who can create a fun and nurturing environment for our little one!

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NEW! Flexible Childcare for Active Boys in Needham

Needham, MA | 18 mi

Start Date: 15 Jan 26
Applications Close: 28 Dec 25

Posted by Ai Ling 36 minutes ago

Job Details: Casual Babysitting

$25 per hour

Calling all energetic and experienced sitters! We need a reliable caregiver for our two awesome boys (ages 5 and 8) in Needham, MA. Exciting Opportunity Highlights: • Competitive Pay: $25-$29 per hour • Flexible Start Date (Targeting January 2026) • Occasional to Regular Hours • Before/After School Support What We're Looking For: • Experience with elementary & preschool-aged children • Safe driving record • Comfortable with light housekeeping • Ability to help with homework • Enjoy creating fun, engaging environments Key Responsibilities: • School drop-off/pick-up assistance • Preparing snacks and meals • Light housekeeping and laundry • Running occasional errands • Driving kids to activities Bonus: Must be comfortable around pets! If you're a responsible, energetic caregiver who loves working with kids, we want to hear from you!

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NEW! Infant Care: Flexible Prof Seeks Nanny

Woburn, MA | 18 mi

Start Date: 06 Jul 25
Applications Close: 20 Dec 25

Posted 41 minutes ago

Job Details: Full-time

$22 per hour

Calling all experienced infant caregivers! 🍼👶 I'm a university professor seeking a loving, reliable nanny for my first child starting this July. Here's what makes this opportunity special: 💰 Competitive Pay: $20-25/hour for a full-time position 📅 Flexible Schedule: Varying hours that adapt to academic life 🕒 Typical Weekly Hours: - Mon-Wed: 6am-4pm - Thurs: 7:30am-3pm What I'm Looking For: • Experienced with infants (0-11 months) • Excellent communication skills • Comfortable with schedule flexibility • Light housekeeping • Non-smoker with own transportation Your day will include: • Infant care & development • Meal preparation • Light household tasks • Adapting to a dynamic family schedule If you love nurturing little ones and thrive in a supportive, academic environment, this could be your perfect role! Let's connect and discuss how we can care for my little one together. 🤱❤️

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Playful Preschool Care - Flexible Hours

Norwood, MA | 18 mi

Start Date: 04 Jan 25
Applications Close: 23 Dec 25

Posted by Iren 7 days ago

Job Details: Part-time

$20 per hour

Are you a fun, responsible caregiver looking for a rewarding part-time position? We're seeking a warm, engaging babysitter for our delightful preschool child in Norwood, MA! Job Highlights: • Flexible scheduling with consistent evening hours • Regular shifts Monday, Tuesday, and Thursday • Time: 5:00 PM - 8:00 PM What We Need: • Reliable sitter with own transportation • Experience engaging with young children • Ability to supervise and interact playfully Responsibilities: • Supervising and entertaining our preschooler • Warming pre-prepared meals • Ensuring child's safety during playtime Compensation: • $18 - $22 per hour • Start date: January 5th, 2025 The ideal candidate is caring, dependable, and loves creating fun, enriching experiences for young children. Your positive energy and nurturing approach will make all the difference!

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Overnight Care for Preschooler on New Year's

Norwood, MA | 18 mi

Start Date: 22 Nov 25
Applications Close: 22 Dec 25

Posted by Iren 7 days ago

Job Details: Casual Babysitting

$20 per hour

Fun, One-Time Babysitting Opportunity! 🧒✨

We're seeking a responsible, caring babysitter for our preschool child during a special evening.

Job Details:
• Date: November 22, 2025 & January 1, 2026
• Time: Flexible, approximately 11:00 AM - 5:00 PM
• Hourly Rate: $18 - $22 per hour

Responsibilities:
• Engage child in fun, age-appropriate activities
• Ensure child's safety and comfort
• Prepare light snacks

Ideal Candidate:
• Experience with preschool-aged children
• Punctual and dependable
• Enjoys creating a positive, playful environment

Looking forward to meeting a wonderful caregiver who can make our child's day special!

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Flexible Afterschool Care for Teen Boy in Needham

Needham, MA | 18 mi

Start Date: 30 Nov 25
Applications Close: 27 Dec 25

Posted by Lindsay 7 days ago

Job Details: Part-time

$28 per hour

Seeking a reliable and responsible caregiver for a laid-back middle school student in Needham, MA! 🏡

Job Highlights:
• Consistent weekly hours: Monday-Friday, 2:30pm - 6:30pm
• Competitive pay: $28 per hour
• Flexible start time and occasional extra hours available

Key Responsibilities:
• Provide afterschool supervision
• Assist with homework
• Prepare light meals and snacks
• Help with transportation (must have valid driver's license)

Ideal Candidate:
• Comfortable with pets
• Responsible high school, college, or grad student preferred
• Reliable transportation

Average ~20 hours per week with some flexibility. Occasional evening or overnight opportunities possible. Great opportunity for a dependable, adaptable caregiver who enjoys working with teens!

Location: Needham, MA

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