207 High St Cambridge, MD 21613

Welcome to possibly the oldest house in the sought-after historic district of Cambridge!
It’s easy to make friends in Cambridge! Especially while sitting in a rocking chair on the front porch of your amazing National Register/Historic District house, right on the beautiful brick High Street in one of the most interesting old cities on the Eastern Shore. Imagine chatting, across your white picket fence, about what it’s like to be the owner of the oldest house in Cambridge! Locals & visitors alike are charmed by this old & storied colonial property. Built when Maryland was a British Colony, the Caile-Bayly house has seen centuries of celebrations & 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 & quirky, one immediately feels a warmth & welcoming sense of comfort to this home, while still maintaining the atmosphere of her long & interesting history & 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 & 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 classic library adds grace & charm where you can spend hours in peaceful enjoyment, beside a sunny window, with a cup of tea & 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 & 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 & 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 & 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, & there are currently three grants in place, funding the initial stages of planning & stabilization. Additionally, local & regional interest in the Cabin has led to the property becoming a part of the Harriet Tubman Underground Railroad Byway, as well as being listed by the National Park Service as a site on the National Underground Railroad.