HOA Assessments


Please remember that the HOA relies upon its members to pay in a timely manner, as the budget is based upon the assessments for the year. The Board understands every homeowner has been impacted in some way by the coronavirus, with financial hardship being the most common.

To help alleviate some of this burden, your coupon booklet for the 2022 HOA dues with monthly payments of $58.24 for 12 months should have arrived in December. 

Payment Options


Please make checks payable to:
Waterside Homeowners Assn of Orange County, Inc.

Mail to:

Sentry Management, Inc.

Attn: Waterside HOA of Orange County 

2180 W SR 434, Suite 5000

Longwood, FL 32779 

To set up a new account* and pay online, access the new payment provider at clickpay.com.

*PLEASE NOTE: You will need to set up a new account if you were utilizing Sentry's previous online payment provider.



We understand that hard times can fall on anyone, so remember your association will always entertain a reasonable payment plan. Should the need for a payment plan arise, please contact the association manager - she will be happy to help.


Jo Ann Donaldson

Community Association Manager


Sentry Management Inc

2180 West SR 434 Suite 5000

Longwood, FL 32779

jdonaldson@sentrymgt.com (preferred)

407-788-6700, ext. 51221

407-788-7488  fax

Once approved by the HOA Board, Jo Ann will contact you to let you know if the terms are acceptable. If approved, this will stop any further late payment fees, intent to lien fees, lien fees, as well as not ruin your credit rating as long as the terms are completed successfully.

What do my HOA Dues
pay for?

The Waterside HOA Assessments include the following:


  • Maintenance of common grounds, retention ponds
    and recreation area.

  • Utilities for fountains, front entrance and irrigation
    in common areas.

  • Insurance for common areas.

  • Ensuring residents are complying with C&R and HOA by-laws.

  • Basic cable service and 60 mbps Internet connection from Spectrum*

  • Sentry Property Management

*Due to Spectrum canceling the bulk contract, we have been exploring options and will provide them at the Thursday, July 28, meeting (see home page for details).