Montessori Toddler Support Teacher​/Guide

Winfield Children's House has an opening for a Support Toddler Teacher/Guide to join our team for the 2026-27 school year. This teacher will work in our Accredited Montessori program as part of our Toddler classrooms for children 16 months through 3 years.

At Winfield we embrace the notion that every person brings value and importance, so we consider every role to be an integral part of our team. The position requires a thoughtful, nurturing, conscientious individual who has worked with young children and is passionate about Toddler education. The best support guides are self-starters, able to maintain a balance between essential daily tasks and flexibly responding to shifting needs throughout the day.

You will come to anticipate and learn the rhythms of the classrooms and the children to know where you can provide the best help in any given moment. You will work with both of our Toddler classrooms, getting to know the all of the teachers and the children in both rooms, and becoming an integral part of our Toddler team.

A Montessori credential or experience in a Montessori Toddler program is a plus, but not a requirement. More important is a recognition of the importance of a solid early childhood program, and a curiosity to learn more.

Our Support Guides often move on to classroom teams in subsequent school years, or even pursue a Montessori credential, which Winfield sponsors teachers to attend. While taking that step is not a requirement, Winfield is committed to helping our teachers achieve their professional goals, so this position could be ideal if you are looking to further your career, or early in your journey, and exploring to find your ideal age group and setting.

In addition to being a valued member of the Toddler team, and working with credentialed Montessori ans in each classroom, you will part of the wider Winfield community made up of four Early Childhood classrooms for children 3-6 years old. Our full-time Outdoor Educator and Art teacher round out our talented and caring teaching staff.

This position is full-time and year-round; during the summer months, a smaller nature and art camp is offered to our enrolled students, providing an opportunity for this position to join one of the camp teaching teams. The position is available now, but we can be flexible on the start date for the right candidate.

Winfield is located in Falmouth, just north of Portland, Maine. Soon to be celebrating its 40th anniversary, Winfield currently serves approximately 100 students from 16 months through 6 years old. Read more about Montessori and our school online at

• Follow schedules and routines
• Establish and maintain positive relationships with students, parents, and co-workers
• Maintain the health and safety of all students
• Prepare the classroom environment for optimal learning
• Attend meetings and staff development

• A high school diploma or higher. Preferred is a Bachelor's or Associate degree, or some college work, ideally in an Early Childhood-related area
• At least one year of experience working with toddlers in childcare, teaching, or other related fields
• Ability to build rapport with children
• Positive and patient demeanor
• Ability to work on the floor or at a table with children, and to help children navigate up and down stairs
• Excellent written and verbal communication skills
• The ability to work collaboratively in a supportive environment

Winfield offers a competitive compensation and benefits package (including medical, dental, short-term disability, and life insurance), commensurate with experience. This position is eligible for participation in the Maine State Early Childhood Educator Workforce Salary Supplement program. The amount provided through that program is determined by the individual's education and experience, and is in addition to the salary range provided here.