
In order to take in views of the Chester River, the rear facade incorporates more windows than the front.
But the newly constructed Chestertown, Maryland home is a reflection of the taste of its owners, Fred and Wanda Sherriff, who envisioned a traditional expression in the venacular of the older homes on the Eastern Shore.
The couple lived outside of Chicago when they purchased the property, but through visits to family in Delaware, and a previous stint living in the area, they became familiar with the Chesapeake Bay and the land of pleasant living. Despite Fred’s upbringing sailing on the lakes around Michigan, “it was a foregone conclusion that the Chesapeake Bay was just the best for sailing,” says Wanda.
This vision for the home took quite a while to formulate and began nearly ten years prior to construction when Fred happened upon the land during a sailing trip and purchased it. But for Fred, who was seeking a home to retire to after a long run as head engineer with Kraft Foods, having plenty of time to plan was key. “That’s just Fred’s nature—to get all his ducks in a row,” says Wanda.
Interviewing a number of architects and builders, the couple began to form their team with Charles E. Anthony, owner of Annapolis’ Charles E. Anthony Architects. After a number of planning meetings with preliminary sketches and ideas reworked at a leisurely pace, a picture in a library book solidified the vision for Wanda. She says the picture of the home was white, clapboard, and had big brackets. “We liked the idea of the brackets and thought it looked country,” she says, adding, “We wanted it to look like there had been an old part of the house and as time passed they added on another little bit and another little bit, so it has different lines.” The facade of the home is reminiscent of the game of Monopoly with a hotel and a few houses plopped down on a block of land. But contrasting the board game—where flashing your fortune is rewarded—this home has a modest style that pays homage to traditional farmhouse detailing.
In keeping with the turn-of-the-century design theme, builder Bert Winchester of Winchester Construction in Crownsville, Maryland says he “looked toward the natural earthly materials that are likely to perform consistently in ways that one knows because they’ve been around for so long.” He adds, “If you want to build a home that’s true to an area, you have to use materials that would be authentic.” These materials included Spanish cedar siding and trim, lead-coated copper roofing, clear heart pine flooring, and custom millwork. He also installed a high-grade European-style exterior door and windows, and a superior insulation package. “When you’re sitting on that bluff, facing North across that river, it really gives them a great comfort in that house to have that kind of weather envelope to protect them from the elements,” says Winchester.

Inside the house, simple yet formal nods to traditional architectural styles dominate much of the living space.
Fred preferred a finely crafted home where he could take in views of his boats docked in the river by his pier, fireplace behind him. Wanda, on the other hand, had more modest goals. She sought country comfort in a home that was easy to take care of, where her clothesline wouldn’t feel out of place. These desires came together in Anthony’s design.
The home is 4,100 square feet, independent of basement and porch space, and is laid out in a linear fashion to allow all major rooms to have a view of the water.Anthony says “The massing steps down, almost as if there were additions to the house over time even though it was all built at once.” It gives the house a faux sense of history. “I wanted this house to look like it was the original farmhouse around which the rest of the community developed,” he adds.
The house is set back away from the road with a driveway nearly 200 feet long that turns into a circle in front of the porch. Two buildings sit separate from the house and act as garages. One is designed to look like a potting shed and the other like a carriage house, according to Anthony. Three cars are housed between the two buildings and, in addition to an attic in one, additional space is used for Fred’s workbench and tools.
Instead of walking in the front door and being hit with a staircase ascending to the family’s sleeping quarters, this home’s foyer has no stairs. As a satisfying alternative, guests step into this cubic entry and are greeted with a peek straight through the living room and out the back of the house to the river, an enticing preview and reminder of the rivers’ emphasis here.
In keeping with a Victorian floorplan, rooms are well-defined. Wanda, not being a fan of open designs (including those that include single rooms reaching two stories), prefers discrete spaces. Despite the conventional layout, the design flows easily from one room to the next because of the arrangement of the doors. Ceilings are high, stairs and hallways are wide, and space is plentiful. “It just makes the house feel very open and yet it still has definite rooms,”says Wanda.
These contained rooms create a cozy sense of warmth in the home, according to Anthony. He says of the dining room, “It’s nice to have that sense of four walls around you. You focus on the family event in that space.” In keeping with the traditional theme, the room walls have a horizontal trim that wraps the room at plate-rail height. “There is some historic precedence for this kind of trim although it was all custom designed for this house,” says Anthony.
The kitchen, however, does have an open design and includes an eat-in breakfast nook, which leads to the deck and patio. A sitting area with fireplace is connected to the kitchen and leads to a screened porch, all with substantial views of the river. Anthony says the screened porch is like a “bird’s nest” because it’s perched a full story above ground and extends out toward the ravine. “It’s very dramatic and probably has the best view toward Chestertown,” he says. Beneath the screened porch is the walk-out basement housing Fred’s hobby room where he builds his model half-boats.
In addition to the rear screened porch, the Sherriffs have the option of enjoying nature on a second rear porch off of the living room or on a third porch connected to the front of the home. “You’ve got areas where you can go to get out in the sun and enjoy the breezes and watch what’s going on whether it’s river side or road side. That was a bonus we didn’t expect—the actual design of the porch to fit with the house so well,” says Wanda.
Gay Crowther of Crowther and Associates Landscape Architects in Annapolis designed “simple, easy, casual places that flow one into another.” She says the homeowners didn’t want anything fussy. Wanda confirms that low maintenance was the way to go as they didn’t want a garden or anything that looked brand new. Wanda says, “Old fashioned” plants and shrubs were added to the landscape and include magnolias, willows, and lilacs. Many of the existing mature trees were kept “to support the sense of history,” says Anthony. Bill Price of B&K Lawn and Landscape carried out the design by handling installation.
Not only did the Sherriffs endeavor to preserve a bit of Eastern Shore history but they also aimed to preserve a bit of Fred’s history as well. Stones that had rested in his grandfather’s yard for two generations were dug up and brought to the new home, creating steps to the river. “We would have had to do something to get to the river, but the fact that it’s this little piece of Michigan that came with us was just great,” says Wanda.
The Sherriffs recognize their dream was brought to life in a collaborative effort. In a multi-page thank you letter to Winchester Construction, the couple wrote, “A custom home is a product of cooperatively harnessing diverse points of view and yielding a product better than any single perspective.” This sentiment is shared by Winchester who reaffirms, “there are a number of people at each job who are part of a team that makes these projects [work] so well.”
Anthony agrees. “For an architect there are two levels of satisfaction: one is having great clients that you feel really happy and good about working with, and then there’s a level of satisfaction about the product itself which is the house. And I feel really good about both of those things.”
Does Wanda have a favorite space in the home? “No. I think that says a lot. I love everything in this place.”
Tanyika N. Lewis is a frequent contributor to ChesapeakeHome magazine.
Contacts:
B&K Lawn and Landscape LLC: 410-778-4445
Charles E. Anthony Architects: charleseanthonyarchitects.com or 410-268-0880
Crowther and Associates Landscape Architects: 410-267-9437
Winchester Construction: winchesterconstruction.net or 410-987-5905







