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What is ParentSquare?

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!
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Community Connect visible in the foreground.

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!
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OCPS Parent Academy

Join Us for a FREE Day of Learning & Fun at Parent Academy! Discover valuable information and resources to support your child's success—all in one place! At Parent Academy, you'll have access to engaging sessions led by district departments and community partners, plus an interactive exhibit hall filled with organizations eager to share helpful tools and services.

Click here to get your ticket!
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Hurricane Season: June 1 - November 30

Hurricanes are dangerous and can cause major damage from storm surge, wind damage, rip currents and flooding.

Click here for helpful resources!
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Bus Route Information for the 2025-26 School Year

Bus route assignments for the upcoming 2025-2026 school year will be available to view on August 1, 2025.

Click Here to Find Your Bus
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OCPS Parent Portal Concerns?

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

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Latest News

Stay up to date on the latest news, events and more with the ParentSquare app!

Upcoming Events

View the full calendar to see all events happening in the next few weeks and months!

School Profile

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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: 5240 Keenes Pheasant Drive Windermere, FL 34786

Phone: 407-654-1351

Principal:Dr. Tracy Webley

Mascot: Cougar

Colors: Blue and Silver

School Hours:  8:45-3:00 (MTRF) and 8:45-2:00 (W)

Grades: Kindergarten – 5th 

Principal’s Message
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Dear Parents and Families,

Welcome to Keenes Crossing Elementary School.  Whether you are returning or joining us for the first time, we are thrilled to have you as part of our school community. At Keenes Crossing, we believe that strong partnerships between home and school are the foundation of student success, and we are committed to working together to ensure every child has an enriching, joyful, and safe educational experience.

Our dedicated teachers and staff work hard on engaging lessons, organizing classrooms, and planning exciting events that foster curiosity, creativity, and a love of learning. Each year, we are especially focused on developing strong literacy and math foundations, building character, and encouraging active participation in our school community.

To help your child have a successful school year, we encourage the following:

  • Stay Connected:  Regularly check our school website, read the weekly grade level newsletters, and sign up Parent Square for updates, important dates, and classroom news.
  • Read Together:  Even just 15 or 20 minutes of reading at home each day can make a big difference in your child’s reading development.
  • Get Involved: Join the PTO, volunteer in the classroom, or attend school events. Your involvement shows your child that education matters.
  • Maintain Healthy Routines: A consistent bedtime, a nutritious breakfast, and daily attendance all support your child’s focus and well-being.
  • Attendance Matters:  Make sure your schloar is attending school and is on time!

Please never hesitate to reach out to your child’s teacher or to me if you have questions, ideas, or concerns. Our doors are always open, and we value your voice.

Thank you for trusting us with your child’s education. Let’s make each school year one of growth, discovery, and joy!

Warmly,

Dr. Webley