ParentSquare is a unified communication platform that offers a variety of tools that allow the district, school administrators and teachers to more effectively communicate and engage with families and students.
Click here to learn more!
If you are experiencing issues with an OCPS Parent Portal Application (i.e. Skyward Family Access, Canvas Parent) please click below for support.
Parent Portal Concerns Form
Need to Locate Resources? You can search for free or reduced cost programs such as food, housing, mental health, education programs, and other social services provided directly by Community Based Organizations.
Click here to learn more!
ParentSquare is a unified communication platform that offers a variety of tools that allow the district, school administrators and teachers to more effectively communicate and engage with families and students.
Click here to learn more!
If you are experiencing issues with an OCPS Parent Portal Application (i.e. Skyward Family Access, Canvas Parent) please click below for support.
Parent Portal Concerns Form
Need to Locate Resources? You can search for free or reduced cost programs such as food, housing, mental health, education programs, and other social services provided directly by Community Based Organizations.
Click here to learn more!
Stay up to date on the latest news, events and more with the ParentSquare app!
School Profile

Vision: Every student graduates prepared and inspired for a thriving future.
Mission: Together with our families and the community, we empower students with a superior academic experience, essential life skills, and boundless opportunities.
Address: 311 N Dillard Street, Winter Garden, FL 34787
Phone: 407-877-5000
Principal: Tiffany Smid
Mascot: Dragons
Colors: Green and Orange
School Hours: 8:30am-2:45pm MTTHF 8:30am-1:45pm W
Grades: PK-5
Principal’s Message
Dear Dillard Street Families and Students,
Welcome to an exciting school year at Dillard Street Elementary! Whether you are a returning Dragon or stepping through our doors for the very first time, we are thrilled to welcome you to our vibrant school community. At Dillard Street, our goal is to establish a strong foundation that ensures every student graduates prepared and inspired for a thriving future. Throughout the school year, our dedicated faculty and staff work hand-in-hand with parents and community partners to provide:
A Superior Academic Experience: Standards-based, engaging instruction designed to challenge and support every learner at their individual level.
Essential Life Skills: Fostering kindness, resilience, teamwork, and leadership inside and outside the classroom.
Boundless Opportunities: Inspiring curiosity and encouraging students to explore new interests and discover their unique talents
To our new students joining the Dillard family: starting at a new school is the beginning of a wonderful adventure! You are entering a warm, caring environment where teachers and classmates are eager to support you every step of the way. Bring your curiosity, your big dreams, and your unique personality—we are so glad you are here, and we cannot wait to see all that you will accomplish!
We firmly believe that education is a team effort. When home, school, and community unite, our students achieve great things. We invite you to stay connected, participate in school events, jjoin the PTA, and maintain open communication with us throughout the year.
Thank you for sharing your children with us. Let’s work together to make this school year filled with joy, discovery, and proud achievements!
Elaine Lundberg
Principal, Dillard Street Elementary
Go Dragons!
