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44 Years
experience
Trusted Preschool & Kindergarten Programs in San Mateo
Founded in 1982 by Cecilia Boland-Walsh, Highland Montessori has provided a nurturing environment for young children in San Mateo for over four decades. Under the leadership of Molly Walsh, the school maintains its founding values while integrating modern, research-based practices in early childhood education. Our mission centers on fostering curious thinkers, empathetic participants, and responsible stewards of society through a curriculum grounded in respect, social justice, and hands-on exploration. We offer year-round preschool and kindergarten programs for children aged 2.5 to 6, emphasizing social, emotional, and academic growth in a home-like setting. Our approach combines the Montessori method with inspiration from the Reggio Emilia philosophy, prioritizing exploration, independence, and collaboration.

Teachers observe children's interests to guide learning, supported by small class sizes and low student-to-teacher ratios. Educators bring expertise in Montessori, Reggio Emilia, and early childhood development, with ongoing professional development ensuring alignment with best practices. Families are active partners in education, contributing to a diverse, inclusive community that values cultural exchange. We believe in creating a circle of care where children, families, and educators feel deeply connected, extending our values beyond the classroom. Our vision is to prepare children not only for academic success but also to inspire lifelong curiosity, empathy, and responsibility.
Services
Preschool Programs Kindergarten Preparation Toddler Development Transitional Kindergarten Family Engagement
Details
  • Year established: 1982
Highlights and features
  • We offer over 40 years of experience in early childhood education.
  • Our teachers hold advanced degrees and specialized Montessori/Reggio Emilia training.
  • Small class sizes ensure personalized attention and relationship-based learning.
  • We integrate Montessori and Reggio Emilia philosophies with research-based practices.
  • Families actively participate in a diverse, inclusive educational community.
What people say
Loves going to school Amazing teachers Safe environment Creative curriculum Daily updates
Services
Preschool Programs
Our preschool programs serve children aged 2.56, focusing on social, emotional, and academic development through Montessori and Reggio Emilia-inspired methods. Small class sizes allow personalized guidance, fostering independence and curiosity. Children engage in hands-on activities that build foundational skills while promoting creativity and collaboration.
Toddler Development
Toddler programs emphasize structured yet nurturing environments where children develop motor skills, language, and social interactions. Teachers use Montessori principles to encourage exploration and self-directed learning. Calm, joyful classrooms support toddlers' emotional growth and early problem-solving abilities through play-based activities.
Transitional Kindergarten
Transitional kindergarten bridges preschool and elementary education, focusing on academic readiness and social-emotional skills. Curriculum incorporates Universal Design for Learning to accommodate diverse learning styles. Children develop literacy, numeracy, and critical thinking through student-centered activities and collaborative projects.
Family Engagement
We prioritize family involvement through regular communication, cultural sharing, and school events. Parents receive daily updates via the Brightwheel app and weekly curriculum summaries. Community-building activities strengthen connections between families, educators, and children, creating a supportive network for holistic development.
Professional Development
Educators participate in ongoing professional development, blending Montessori certification, Reggio Emilia training, and early childhood research. This ensures alignment with best practices while maintaining individualized teaching approaches. Collaborative learning among staff enhances classroom innovation and child-centered pedagogy.
People
Molly Hanlon
School Director
Molly Hanlon holds a Child Development degree with Montessori training from MTEC and Reggio Emilia certification from Italy. She is completing her Master's in Educational Administration and has over a decade of experience leading Highland Montessori's inclusive, child-centered programs.
Jlia Ritort
Assistant Director
Jlia Ritort earned a Bachelor's in Translation and Interpreting from Pompeu Fabra University and has 15+ years of education experience. She joined Highland in 2020, combining international perspective with professional growth to support children's development.
Heidi Rivas
Lead Preschool Teacher
Heidi Rivas holds an Associate's in Child Development and a Bachelor's in Psychology with Montessori training. She has three years of classroom experience at Highland, specializing in fostering independence and confidence in young learners.
Ana Castro
Lead Toddler Teacher
Ana Castro earned a Montessori Credential and a degree in Child and Adolescent Development from San Francisco State University. With nearly a decade of teaching experience, she creates calm, joyful toddler classrooms rooted in structure and compassion.
Sarah Crellin
Lead Transitional Kindergarten Teacher
Sarah Crellin holds an M.A. in Education with expertise in learning theory and technology. She has eight years of classroom experience designing student-centered lessons that emphasize voice, choice, and confidence in transitional kindergarten settings.
Questions
What age groups do you serve?
We serve children aged 2.5 to 6, offering toddler, preschool, and transitional kindergarten programs.
What educational philosophies do you follow?
We combine Montessori methods with Reggio Emilia inspiration, emphasizing hands-on learning, independence, and collaboration.
How do you involve families?
Families receive daily app updates, weekly curriculum emails, and participate in school events to build community connections.
Are meals provided?
Yes, we provide healthy lunches and snacks as part of our program.
Can I schedule a tour?
Contact us to inquire about tour availability, which depends on enrollment openings and scheduling.
Do you offer extended care?
Our standard hours are 8:00 AM–4:00 PM, with limited flexibility based on staff availability.