When new owners acquired a historic estate on the banks of Maryland’s Choptank River as a weekend retreat, they also inherited a ramshackle caretaker’s cottage on the property. Hoping to turn it into a charming guesthouse for visiting friends, they tapped architecture firm Becker Morgan Group and Ilex Construction to helm the project. Due to its dilapidated condition, the existing structure required an extensive renovation, but “because of Chesapeake Bay code parameters, we had to adhere to the original footprint,” says lead architect Christopher Pattey. The clever solution: Changing the roofline not only created a more inviting façade, it allowed for more usable square footage on the second floor.

Now, with 1,084 square feet of living space—plus a screened porch—the revamped two bedroom, two-bath cottage feels airy, thanks to an open plan and the implementation of larger windows. On the exterior, crisp, white siding and a cedar-shingle roof echo the elegant look of the main residence. The design team also contributed two all-new structures in a similar style: a pool cabana and a four-car detached garage with guest quarters above it. “All the buildings were designed so that the architectural aesthetic would have continuity,” shares Pattey. “This vernacular is so timeless to the Eastern shore; it’s as relevant today as ever.”