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About Schoolfield Properties

Our Founders, Wanye and Dianne Schoolfield - Schoolfield PropertiesWayne and Dianne Schoolfield founded Schoolfield Properties back in 1969. Wayne served as President and CEO acquiring, developing and brokering real estate; while Dianne served as Secretary/Treasurer managing the financial aspects of their business. Originally, the company was established to broker and develop residential property in and around Osceola County. In its first three decades, the couple developed and sold over 32 single family subdivisions such as Camelot and Regal Point – the first and second security gated subdivisions in Osceola County – Canoe Creek Woods, Pine Chase Estates, The Woods, Regal Oak Shores, Regal Bay, and Regal Cove.

In the late 80’s, the couple realized the commercial potential in St. Cloud, Florida and bought, developed, and sold much of the commercial landscape we see there today, composed of several shopping centers and office parks such as Home Depot, Publix, Walmart, Sun Bank, St. Cloud Post Office, and Blackberry Creek.

In the late 90’s, the couple’s three children Cheryl, Kevin, and Brian Schoolfield took interest in the real estate business and the family devised a plan to long-term hold the commercial developments and investments they developed and acquired. At that time, Osceola Management was established to maintain their family’s portfolio.

Today, the Schoolfield family jointly and separately own close to 1.5 million square feet of commercial office, warehouse, retail, medical, and ground leased properties. Although the majority of their portfolio exists in Osceola County, they own investments throughout Volusia, Orange, and Brevard Counties.

Wayne and Dianne now spend most of the year traveling around the world. Together they have visited over 125 countries, with the balance on their bucket list. Dianne also enjoys doing needlework and Wayne gardening.



  • Board member of Reedy Creek Improvement District, Walt Disney World, since 1994
  • Director of SunTrust Bank, N.A. Orlando
  • Member of SunTrust Bank, N.A. Executive & Trust Committees Orlando
  • Advisory Board of SunTrust Bank, N.A. Osceola County for 15 years
  • Board of Directors of the Economic Development Commission of Central Florida and member of the Executive Committee
  • Board of Directors of the Community Foundation of Central Florida Distribution Committee
  • Board of Directors and Chairman of Kissimmee – Osceola County Chamber of Commerce
  • Board of Directors of the Orlando Chamber of Commerce
  • Member and Chairman of First United Methodist Church Kissimmee Finance Committee
  • Member of First United Methodist Church Kissimmee Trustees
  • Orlando District Board of Mission & Church Extension Methodist Church
  • Advisory Board Member of Visiting Nurse Association
  • Vice Chairman of St. Cloud Economic Development Board
  • Member of City of Kissimmee Planning & Zoning Board for 12 years, 2 years as Chairman
  • Vice Chairman of Osceola County Planning & Zoning Board
  • Member of the Osceola County Transportation Committee
  • Walt Disney World Community Service Award Committee
  • Vice Chairman of Governmental Affairs Kissimmee – Osceola County Chamber of Commerce 1991
  • Member of CDD Board in Celebration (Walt Disney)
  • Review Committee for all United States Military Academy Appointments under Congressman Bill McCollum
  • Vice Chairman Kissimmee/Osceola County Economic Development Commission Governmental Affairs 1989
  • Valencia Community College Foundation Board Member


  • Served on many committees at First United Methodist Church Kissimmee
  • Member of the Board of Directors and past Chairperson of Osceola County Council on Aging