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.


2020 Homeowner's Association Dues 
Annual 2020 Homeowner's Association Assessments due 31-January-2020:
  • Age-Restricted Area              $1,097
  • Non-Age Restricted Area       $   397 
Community Information | Notices

Sleepy Hollow Lawn Care


 BULLETIN -- Irrigation Schedule Update – Effective 14 October, 2019


Legendary Landscape Inc. has changed the irrigation system schedule as follows:


  • The irrigation system has been turned off and will remain so unter further notice.
  • Per 2019 Irrigation Guidelines, Legendary Landscape, the HOA contract irrigation professional, has complete control of the community irrigation schedule.
Schedule for Irrigating Lawns - 2019 

Effective Ma 24, 2019, the irrigation system is set to run on Monday, Wednesday, Friday and Saturday.  The irrigation zones are programmed to start in the early evening and run into the follow morning.

The programmed sequence is set to provide the best benefit to the entire community.  Adjustments to the schedule will be made as prevailing weather conditions and the season changes.

IMPORTANT:  If you notice something that appears abnormal, for example, your yard is overly saturated or water is hitting your home, please report the issue or your concerns via The Sleepy Hollow HOA Website at www.sleepyhollowmd.com on the <Home> tab under the section titled Reporting Lawn or Irrigation System Problems/Concerns.

Community Yard Sale


Thank you for participating in our 2019 Fall Community-wide Yard Sale Event held on Saturday, October 5, 2019.  Check back in the Spring for news about our 2020 event.


Sleepy Hollow Socials


* * STAYED TUNED –> Upcoming Events will be posted soon * * 


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
         Cheryl Brophy, Vice President
         [Open], Treasurer
         Karon Dennis, Secretary
         Sue Revelle, 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