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
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 Chairman
Encore 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 Secretary
Encore 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 Secretary
Encore 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 Secretary
Encore 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 2027 at 1:00 pm at the Margaritaville Resort Orlando, 8000 Fins Up Circle, Kissimmee, FL 34747 on the fourth Thursday of each month with exceptions indicated as follows:
October 22, 2026
January 28, 2027
February 25, 2027
March 25, 2027
April 22, 2027* Embassy Suites, 3151 Sunset Walk Dr., Kissimmee, FL 34747
May 27, 2027
June 24, 2027
July 22, 2027
August 26, 2027
September 23, 2027
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