• Our School

    Windermere Preparatory School's academic approach is built on complex problem solving and critical thinking and culminates with the International Baccalaureate (IB) Diploma Programme.

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  • Academics

    Learn more about our Academic Plan, Core Values, Rigorous Curriculum and more.


  • Students

    Students at WPS experience academics, arts, athletics, community service and extracurricular activities.

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  • Fine Arts

    At Windermere Preparatory School, the Fine, Media, and Performing Arts are an integral part of our curriculum enhanced by a unique collaboration with The Juilliard School.

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  • Admissions

    The Admissions Office looks forward to working with your family through every step of the Admissions Process.

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  • Boarding

    The Boarding Program offers students an exceptional global opportunity, first-class education, and a safe home environment.

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    Stay up-to-date on the latest news, information, and events for WPS.


Gary Conroy

Gary Conroy

Director of Entrepreneurial Studies

Gary is a serial entrepreneur, educator, and business consultant. Born in Dublin, Ireland, Gary moved to the United States and began a distinguished career in entrepreneurship and entertainment asset management and ownership. An American citizen since 2001, Gary has built several companies ranging from commercial real estate management, a restaurant investment group, and a consultancy group.

Today, Gary’s career is anchored in bringing entrepreneurship education to as many people as possible as the Founder of the Startup Studio. Gary currently holds the position of Director of Entrepreneurial Studies for Windermere Preparatory School. He passionately believes in integral management solutions that hinge around building teams with talented and sophisticated partners that share his fundamental focus on creativity, strong network building, and the true power of relationships.

Gary is also a multiinstrumentalist, songwriter and producer. Gary has merged these disciplines with his business acumen to found CC Music LLC. CC Music is rooted in developing amazing artists with a focus on reshaping how the music industry represents them and represents the collaboration of a team of incredibly talented people focused on creating amazing music and fostering true artistry. Gary resides in Winter Garden, Florida with his wife Dana and their three daughters, Casey, Madi and Emma.

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