Caile-Bayly House

  • $595,000
207, High Street, Cambridge, Dorchester County, Maryland, 21613, United States
Featured For Sale National Register of Historic Places

Caile-Bayly House

207, High Street, Cambridge, Dorchester County, Maryland, 21613, United States
  • $595,000


Haven’t you been dreaming of living in a truly historic house? This is a rare opportunity to experience all the enjoyment of living on a property that’s well-known in the region. There are tales to tell- history to explore! Be the person that is interviewed by the local newspapers and TV stations. See tour groups pause on the sidewalk to hear about the history: they will be in awe that YOU are the owner of such an amazing place!!

Imagine chatting across your white picket fence about what it’s like to be the owner of the oldest house in Cambridge! Locals and visitors alike are charmed by this old and storied colonial property. Built when Maryland was a British Colony, the Caile-Bayly house has seen centuries of celebrations and changes, passing from one generation to the next of the Bayly family for nearly 200 years. The current owner is only the sixth time it’s changed hands since the 1740s! Are you ready to be the 7th?!

The rooms are spacious for its times, largely unchanged throughout the years. Cleverly blending in all the modern conveniences, there are tons of closets and storage space.  Charming and quirky, you immediately feel a warmth and welcoming sense of comfort to this home, while still maintaining the atmosphere of her long and interesting history and the many generations that have filled it with love and laughter.

Original wide-planked hardwood floors are immediately apparent in the oldest sections, pleasantly worn by the tred of centuries of family and friends. Nearly all of the solid-wood doors feature rim locks, a few even have working skeleton keys! An unusually wide staircase invites you to explore the upstairs. With six fireplaces sprinkled throughout the house, you can easily imagine relaxing before a fire as snow falls gently outside the large original nine-over-six paned wavy-glassed windows. These huge windows were designed to allow for those lovely cross breezes to flow through the house on bright Spring days.

The classical library adds grace and charm where you can spend hours in peaceful enjoyment, beside a sunny window, with a cup of tea and a good book. And while every room on the ground floor is unique, you must see the indescribable original kitchen! Passing from the library through a hyphen addition that includes two huge pantries and a separate walk-in butlers pantry, you find yourself in the incredible kitchen with its breathtaking 5 foot tall inglenook fireplace built into a beautiful old brick wall on your right, while on the left side is a completely modern kitchen. Much joyful entertaining goes on in this space!!

With four bedrooms and two full bathrooms on the second floor, there’s plenty of room to find your own private space. One of the bedrooms even has its own private back staircase!! And while there are over 3000 square feet of fully finished living space, don’t overlook the three (!) full sized “attics”, another 800+ square feet of hardwood flooring, which were clearly finished and occupied rooms in earlier times, including small closets and even a fireplace!!

Beyond the kitchen is another hyphen- a huge laundry/utility and work room. This connects the house to the smoke house, currently fitted as a workshop- perfect for all those little projects around the house- an architecturally unusual building that has fascinated the historians in recent years. Even more interesting is the small cabin in the yard, which has been explored and excavated by State archaeologists over the last few years, revealing hundreds of artifacts that suggest the building might have been one of several slave cabins known to have existed on the property during the 19th century. Consequently, an effort has been underway to preserve the Bayly Slave Cabin, and there are currently three grants in place, funding the initial stages of planning and stabilization. Additionally, local and regional interest in the Cabin has led to the property becoming a part of the Harriet Tubman Byway, as well as being listed by the National Park Service as a site on the National Underground Railroad, Network to Freedom. Numerous Heritage tours of the area count the Caile-Bayly property as a point of particular interest.

This property is a treasure, with a huge yard that contained a renowned boxwood garden during the 19th and 20th centuries. Overlooking a very historic church and cemetery, the entire property is steeped in local history. This type of property rarely comes onto the market, and won’t be available again for many years. If you have dreamed of being a part of living history, this home will make your dream come true!!

The Caile-Bayly House has, in its past, been a site of enslavement. Through archaeological work, a cabin that is believed to have been the home of an enslaved person has been discovered on the property. It is significant as a rare extant example of this dwelling type in its original urban setting. Current owner permits public access to the cabin, as an educational site, a limited number of days per year. The next owner of Caile-Bayly House has before them an invaluable opportunity to support an ongoing research and restoration project, and to contribute to the local historical record.


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Updated on May 3, 2022 at 6:15 pm


  • Address 207 High Street
  • City Cambridge
  • State Maryland
  • Zip/Postal Code 21613
  • Country United States

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Catherine Morrison
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