The Administration Department is responsible for:

  • Providing the overall direction for the Town in accordance with the policies established by the Town Council
  • Assuring that operations are conducted economically, efficiently, and effectively
  • Overseeing programs, operations and policies
  • Preparing, reviewing, and monitoring the annual operating budget for the Town


The Town Manager is responsible for:

  • Making recommendations to the Council
  • Implementing any action taken by the Council
  • Making budget recommendations to the Town Council
  • Overseeing Town departments


Robert Smith

Town Manager
Office: (407) 876-2563 x 5324
Cell: (407) 797-5004
Fax: (407) 876-0103


The Executive Assistant is responsible for:




  • Dissemination and advertising of agendas
  • Farmer’s Market Information
  • Food Truck information
  • Information related to/coordination and advertising of Town events
  • Meetings with the Town Manager
  • Notary services (only for Town residents)
  • Orange County water hookup requests
  • Website/social media updates and post design
  • Windermere mobile app alerts and updates
  • Windermere Gazette (quarterly publication) Advertising and design


The Administrative Assistant is responsible for:



  • Film Permit
  • Garage Sale Permit
  • Open House Permit
  • Right-of-Way Use Applications
  • Special Event Permit
  • Tree Removal Application
    Per FL Statute 163.045:
    • Tree pruning, trimming, or removal on residential property.—
      (1) A local government may not require a notice, application, approval, permit, fee, or mitigation for the pruning, trimming, or removal of a tree on residential property if the property owner obtains documentation from an arborist certified by the International Society of Arboriculture or a Florida licensed landscape architect that the tree presents a danger to persons or property.
      (2) A local government may not require a property owner to replant a tree that was pruned, trimmed, or removed in accordance with this section.



Diane Edwards


Theresa Syphers


Executive Assistant
Office (407) 876-2563 x 5321
Fax: (407) 876-0103
(Monday – Friday; 8:00am – 5:00pm)


Administrative Assistant
Office: (407) 876-2563 x 5327
Fax: (407) 876-0103
(Monday – Friday; 8:00am – 5:00pm)



**Please note that only residents of the Town of Windermere are eligible to purchase park pass/boat ramp keys and tennis keys. Additionally, only residents need to apply for permits to remove trees or hold garage sales/open houses. Not every person with a “Windermere” street address is actually part of the incorporated Town.

Please verify your address is part of incorporated Windermere before filling anything out.  The current HOAs that are part of the incorporated Town are below (please note, Summerport, Casabella, Keene’s Pointe, Belmere, the area surrounding Reams Road, etc. are *NOT* within Windermere. Additionally, there are no condos, townhomes, or apartments within Town limits.):

Lake Crescent Reserve
Marina Bay

Sunset Bay
The Manors
The Willows at Lake Rhea

Windermere Oaks
Windermere Reserve

You may also check on the Orange County Property Appraiser website (non-residents with a Windermere street address will show municipality as “Un-Incorporated”): Orange County, Florida Property Appraiser Website. The Town Office can also quickly verify if you are incorporated for you.