Rolling Oaks Community Development District
Est. 2014 Located In OSCEOLA County, Florida
The Rolling Oaks Community Development District is a local, special purpose government entity authorized by Chapter 190 of the Florida Statutes as amended, and created by ordinance of Osceola County as an alternative method of planning, acquiring, operating and maintaining community-wide improvements in planned communities. A CDD provides the “solution” to Florida’s need to provide valuable community infrastructure generated by growth, ultimately without overburdening other governments and their taxpaying residents. Community Development Districts represent a major advancement in Florida’s effort to manage its growth effectively and efficiently. This allows a developer to establish higher construction standards, meanwhile providing a long-term solution to the operation and maintenance of the community’s facilities.
For more Information regarding the CDD, Please contact the Management Offices at:
Governmental Management Services-Central Florida, LLC:
219 E. Livingston St.
Orlando, FL 32801
Tel: (407) 841-5524
Public Records
AGENDA
FISCAL YEAR 2026
FISCAL YEAR 2025
FISCAL YEAR 2024
FISCAL YEAR 2023
MINUTES
FISCAL YEAR 2025
FISCAL YEAR 2024
FISCAL YEAR 2023
THE CUSTODIAN OF PUBLIC RECORDS FOR THE DISTRICT IS GOVERNMENTAL MANAGEMENT SERVICES- CENTRAL FLORIDA, LLC. TO REQUEST PUBLIC RECORDS FROM THE DISTRICT YOU MAY CONTACT THE CUSTODIAN AT 219 E. LIVINGSTON ST. ORLANDO FL, 32801 TELEPHONE: 407-841–5524 FAX: 407-839-1526 EMAIL: RECORDREQUEST@GMSCFL.COM
BOARD INFORMATION
-
John Chiste ChairmanEncore Funds
1 Town Center Road, Suite 600
Boca Raton, FL 33486
Seat #1
Elected: 11/21/24
Term Expires: 11/2028
County: Palm Beach
E-mail: john.chiste@encorefunds.com -
Jared Bouskila Vice ChairmanEncore Funds
1 Town Center Road, Suite 600
Boca Raton, FL 33486
Seat #4
Elected: 11/17/22
Term Expires: 11/2026
County: Palm Beach
E-mail: jared.bouskila@encorefunds.com -
Cora DiFiore Assistant SecretaryEncore Funds
1 Town Center Road, Suite 600
Boca Raton, FL 33486
Seat #3
Elected: 11/7/22
Term Expires: 11/2026
County: Palm Beach
E-mail: cora.difiore@encorefunds.com -
Penny Lozano Assistant SecretaryEncore Capital Management
3228 Inspiration Drive
Kissimmee, FL 34747
Seat # 5
Appointed: 04/24/25
Term Expires: 11/2026
County: Osceola
E-mail: penny.lozano@encorefunds.com -
Peter Christopher Brown Assistant SecretaryEncore Capital Management
1 Town Center Road, Suite 600
Boca Raton, FL 33486
Seat #2
Elected: 11/21/24
Term Expires: 11/2028
County: Palm Beach
E-mail: peter.brown@encorefunds.com
Board of Supervisors
Meeting Dates
Meeting Dates
The Board of Supervisors of the Rolling Oaks Community Development District
will hold their regularly scheduled public meetings for Fiscal Year 2026 at 1:00 pm at the Margaritaville Resort Orlando, 8000 Fins Up Circle, Kissimmee, Florida 34747 on the fourth Thursday of each month as follows:
October 23, 2025
March 26, 2026
April 23, 2026
May 28, 2026
June 25, 2026
August 27, 2026
September 24, 2026
In addition to the dates above, the Board of Supervisors will hold another portion of regularly scheduled public meetings for Fiscal Year 2026 at 1:00 pm at the Embassy Suites by Hilton Orlando Sunset Walk, 3151 Sunset Walk Drive, Kissimmee, Florida 34747 on the fourth Thursday of the below listed months:
January 22, 2026
February 26, 2026
July 23, 2026
Management Services

GOVERNMENTAL MANAGEMENT SERVICES LLC – CENTRAL FLORIDA LLC
Governmental Management Services (GMS) is a family of limited liability companies that was established on November 26, 2004 for the purpose of providing special district management services to Community Development Districts (CDD). GMS currently has offices in Orlando, St. Cloud, Ft. Lauderdale, Tallahassee, Port St. Lucie, St. Augustine, and Jacksonville, Florida, and Knoxville, Tennessee. GMS currently manages over 275 Community Development Districts across the State of Florida.
Contact Info
Rolling Oaks CDD
219 E. Livingston St.
Orlando, FL 32801
Tel: (407) 841-5524 or (877) 855-5251
Fax: (407) 839-1526
Florida Public Records Notice: Emails to and from Community Development District’s are public record according to Section 119 Florida Statutes. For more information, please see http://www.myflsunshine.com/.
District Manager
Tricia Adams
tadams@gmscfl.com
