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Welcome to Windward Key 

On behalf of the Homeowners of Windward Key, we would like to welcome you to our website. Whether you are just browsing or looking for a new home, we are sure you will enjoy the area and all the amenities it has to offer. The purpose of this website is to introduce you to our community and highlight some of our amenities.

 

There are many advantages for moving into a development such as Windward Key. Rather than go to the expense of purchasing a single unit beach front home with a swimming pool, multi-sports court, and marina, you can buy a townhouse and share the cost of the amenities with your friends and neighbors. At Windward Key there is a natural attachment between neighbors who are there to help in times of need and to share in the good-times. It is a community of diverse, like-minded people, who enjoy the water, brilliant sun rises, and have a strong sense of community spirit while sharing the common area amenities. How we maintain the common area and the aesthetic appearance of each home reflects upon the value of the community as a whole. It is thus necessary to implement various rules and regulations—some required by federal, state, local laws and others established by the Windward Key Owners. These laws and rules are called governing documents.

 

The Windward Key Homeowners Association is governed by a Board of Directors (Board) elected by the Owners. The Owners have entrusted the Board to manage the Association assets. It is not a task that I or the Board takes lightly. We must exercise due diligence to oversee that the organization is well managed and its financial situation remains sound. As stewards of the Owners trust, each Board member and Committee member must always act for the good of the Corporation, rather than for the benefit of ourselves. We must exercise reasonable care in all our decisions without placing the organization under unnecessary risk.

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This means that while working within the confines of our Governing Documents we must strive to meet the needs and desires of the majority of the homeowners. The operative word is strive—we know we cannot satisfy everyone—what we can promise is to consider everyone’s opinion through open and transparent dialog. To confirm our promise, the Board has established a Code of Ethics     to guide the Board and Committee members in their conduct when taking actions on behalf of the Association. The Code of Ethics may be found under the Living Here Tab on the menu above.

 

I do hope that you find our website informative. Our Living Here  pages will give you more details on our amenities, governing documents, living on the bay, and special events that we celebrate. The Local Area pages will connect you with Calvert County, and the Towns of Chesapeake Beach and North Beach. We also provide a Photo gallery of pictures taken from Windward Key and a list of Windward Key homes that are either up for sale or for rent in the Classifieds  page.

 

Again, welcome to the Windward Key website and if you have any questions please send them by submitting your question through the Contact Us tab on the menu.

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Board of Directors,

Windward Key Homeowners Association

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2025 Calendar

 

March 8, 2025: 10:00am 1st Qtr HOA Meeting 

Northeast Community Center (next to waterpark) 

Open to all WWK residents

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May 24, 2025 11:00 am, Pool's Opening Day

 

June 14, 2025 10:00am, 2nd Qtr HOA Meeting 

Northeast Community Center (next to waterpark) 

Open to all WWK residents 

 

July 3, 2025:  At Dusk,

Chesapeake Beach Fireworks 

                

Sept 1, 2025 - Pool's Last day

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​​​​Sept 14, 2025 9:00am - Annual Coffee & Donuts 

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Sept 13, 2025  (Time -TBD)​ - Annual Picnic

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Sept. 20, 2025 10:00am, 3rd Qtr HOA Meeting

Northeast Community Center (next to waterpark) 

Open to all WWK residents

                        

Nov. 1, 2025 10:00 am, Annual 4th Qtr HOA and Budget Approval Meeting at Northeast Community Center (next to Waterpark)

Open to all WWK residents

Swimming Pool

Enjoy the Salt Water pool and socializing with your neighbors, friends, and family.

Marina

Walk out of your home and on to your boat that could be docked right in your back yard. 

Recreation

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Enjoy the evening with a game at the Multi-Sports Court on the Bay.  While playing with a friend or friends and enjoy the beautiful surrounding.

Our Beach

Enjoy the Beach with all the beautiful bay wildlife that call Windward Key home. Take a stroll and find shells and sharks teeth along the shore.

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