Our Community

The Board of Directors of The Villages at Sleepy Hollow Homeowner’s Association, Inc. (HOA) welcomes you to the community’s website. The information contained on the website is meant for both those seeking general information about The Villages at Sleepy Hollow as well as providing community residents with access to community specific information.

The Villages at Sleepy Hollow is situated on the west side of the City of Salisbury, Maryland, which has an estimated population of 26,000 residents. The city was incorporated in 1854 and is the largest city on the Eastern Shore of Maryland. Situated in the heart of the mid-Atlantic region both Wicomico County , which is considered the “Crossroads of Delmarva”, and the City of Salisbury are convenient to shopping and the area’s beaches and Chesapeake Bay recreation destinations. The second largest port and the second largest airport in the State are located in Wicomico County.

The 70.8 acres that make up The Villages at Sleepy Hollow community was purchased by the developers in August 2001. The ground breaking for construction of 193 residential units made up of both single family and duplex homes occurred in October 2003. The classic book, The Legend of Sleepy Hollow, was used as a source for both the name of the community and the names of the streets within the community. A clock tower circle serves as the focal point for this thriving residential community, a portion of which is designated as a 55+ adult living area. Being located within the city limits means the community enjoys access to both city utilities and services in addition to those services provided by the HOA.



Homeowner's Association Dues

Annual 2020 Homeowner's Association Assessments due 31-January-2020:
  • Age-Restricted Area               $1,097
  • Non-Age Restricted Area        $   397 
Annual 2021 Homeowner's Association Assessments due 31-January-2021:
  • Age-Restricted Area              $1,083
  • Non-Age Restricted Area       $   394


Community Information | Notices

News & Announcements

Call For Nominees

Are you looking for a unique leadership opportunity?  Well, look no further!  Sleepy Hollow is looking for leaders like you to join the board of directors. In preparation for our Annual Meeting & Election, the Nominating Committee is looking for a slate of candidates.  We have three (3) board positions open for the March election.  

  • 2 – Non-Age              1 for a 1-year term (Expires 2022); 1 for a 2-year term (Expires 2023)
  • 1 – At Large               1 for a 2-year term (Expires 2023)

If interested, please contact us at the address below for additional information, and to set a time to discuss the future of The Villages at Sleepy Hollow HOA.

Community Yard Sales - 2021

To allow residents time to prepare for their individual yard/garage sales, we are publishing the 2021 Community-wide Yard Sale dates as follows:


Scheduled Date

Rain Date


May 1

May 8


October 2

October 9



* Curbside Recycling – The City of Salisbury *

[Effective Week of March 23, 2020]

Until further notice, The City of Salisbury has suspended curbside recycling pick-up during the once a week trash collection. Recycle items can be placed in your trash can for the normal collection on Tuesday mornings. Any questions regarding this service should be directed to the City’s Field Operations Department at 410-548-3177.

* Neighborhood Courtesy Request *

As good homeowners, we strive for that perfect neighborhood.  In doing so, we need to remember to pick up trash in our yards. Specifically, the Wicomico Weekly is delivered on the hard shoulder of driveways. To prevent this paper from being scattered in your neighbor’s yard or down the street, please pick up at your earliest convenience. If you do not want to receive the paper, call the Wicomico Weekly office at 410-845-4620 and request to be removed from their delivery list. Thank you for being a good neighbor.


Sleepy Hollow Lawn Care

IRRIGATION ALERT – Effective 24-September, 2020

The Irrigation Contractor has amended the programmed run time for the system.  Run schedule will now be MONDAY and  FRIDAY. 

 * * * * 

BULLETIN – Irrigation Schedule Update – Effective 20-July, 2020

  • Scheduled run times will be SUNDAY, MONDAY, TUESDAY and FRIDAY.
  • Watering zones will commence around 11 PM and continue their cycles through the next morning. [Revision became effective 01-July]
Example ~~ Run day for Monday will start approximately 11 PM Monday evening and flow into Tuesday until the entire zone is completed.

Schedule for Irrigating Lawns - 2020 

The community Irrigation System is now up and running.  

  • ·       Scheduled run times are Monday, Wednesday and Saturday
  • ·       Watering zones will commence around 11 PM and continue their cycles through the next morning. 
    As an example, the “run day” for Wednesday will start at approximately 11 PM on Tuesday evening and flow into Wednesday until the entire zone is completed.  

As in past seasons, the system schedule (run day) is subject to change without notice based on prevailing weather conditions.  Any known changes will be updated on Sleepy Hollow’s website (www.sleepyhollowmd.com) and the social network, NextDoor (https://nextdoor.com). 

Refer to the Lawn and Irrigation Guidelines on how to report issues.

~ Posted 3-June, 2020

Sleepy Hollow Socials


* * Upcoming events will be posted when available * * 


Neighborhood Watch 

August, 2016

Residents of the Sleepy Hollow neighborhood had new Neighborhood Watch signs installed and celebrated the occasion with the Mayor and police officers. 

Suspicious Activity – Updated 11-October, 2018


A resident on Tappan Lane has reported to the police that someone has been ringing the doorbell late at night, but when the resident goes to the door no one is there.  Just a note of caution and to advise you to report similar activities to the Salisbury Police Department (SPD) at 410-548-3165.


When you call to report suspicious activity, you aid not only the Police Department, but you make your neighborhood a safer place in which to live and work. A suspicious activity is an occurrence that is out of place in your neighborhood.


UPDATE: The SPD will be on patrol in the area. They suggest that you do not answer the door if you are not expecting someone and that you immediately notify the police.


Follow these steps when reporting a crime to the police:

·       Remain calm

·       Call 9-1-1

·       Identify yourself (name, address, and phone) and give your location

·       Describe what is happening or what you saw happen

·       If there is a suspect or vehicle, be able to provide the police dispatcher with a detailed description and the direction of travel

·       Be patient



Contact The HOA Board:

Email:           sleepyhollowmd@outlook.com
By Phone:     410-430-9544
Mailing Address:
         The Villages at Sleepy Hollow HOA, Inc.
         P.O. Box 5004
         Salisbury, MD 21802

Current HOA Board of Directors:

         Robert Holland, President
         [Open], Vice President
         [Open], Treasurer
         Karon Dennis, Secretary
         Sue Revelle, Board Member
Wendy Bailey, Board Member


Reporting Lawn or Irrigation System Problems/Concerns:

By Email -- Select One Of The Following:
Age Restricted Area Of Community
Non Age Restricted Area Of Community