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 2021 HOA dues for monthly payments of $55.66 for 12 months will be arriving 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 pay online, access mysentrypay.com.

  1. Click the tab “Find Me” and enter your 16-digit account number or click “Search by name.”

  2. Follow the instructions to complete registration.

  3. Click on the tab for “One Time Payments” or “Schedule AutoPay.”

  4. Enter payment amount and payment date.
    If setting up auto payment, select the start date, frequency of payments and end date.

  • A fee is not assessed for registered e-check payments.

  • Make one-time or recurring registered payments or establish a new login ID and password. 

  • Payments made after 4 p.m. ET will be processed the next business day.

  • •ou must be a registered user to make one-time or recurring registered payments.

  • A fee of $14.95 will be assessed for credit card payments.



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.


Teresa Toole

Community Association Manager


Sentry Management Inc

2180 West SR 434 Suite 5000

Longwood, FL 32779

ttoole@sentrymgt.com (preferred)

407-788-6700, ext. 51214

407-788-7488  fax

Once approved by the HOA Board, Christy 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

  • Use of the recreation area, lake dock and ramp

  • 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