Just a few blocks away from the center of Chestertown’s downtown is this property on a narrow and deep lot like others along the urban streetscape. Unlike its neighbors, this house has the advantage of abundant sunlight on one long side of the house due to its sharing of a property line along a neighboring church’s side yard. The long driveway leads to a two-car garage at the rear of the property.
“Highcroft” may have been named for both its street and “croft” was probably added by someone of Scottish descent since it refers to a small farm in rural Scotland.
Set back from the street by the Town brick sidewalk and a grassy area with mature trees, the house telescopes down from the 1840 three story part to the 1780 two story part to the most recent one story addition. The front façade is more articulated than the side facades with a layer of arrow shaped trim over the cornice, shutters and the full front porch with its hipped roof.
Between the house and the two-car garage is a spacious brick terrace enclosed by a combination of different fencing materials from the white pickets along the church’s side yard, the dense privet hedge at the garage and a solid wood fence along the driveway to provide privacy for the terrace. The garage’s pergola’s vines will soon provide their seasonal color.
It’s quite unusual to find a two-car garage in the heart of the Historic District and this garage also has storage above. The wood pile and trash/recycle cans are discreetly hidden behind the garage. The long driveway provides ample off-street parking for guest cars.
The rear wall of the last addition containing the one-story family room is infilled with sliding doors overlooking the deep brick terrace in a herringbone pattern. At the driveway side, tall crape myrtles that define the border between the driveway and the terrace will soon burst into bloom to also add color and softness to the hardscaped area. I noted the “rain chain” leading to a barrel at the corner of the family room-so much more environmentally friendly than downspouts!
The privacy of the deep terrace creates an oasis for relaxation and the fab outdoor oven between raised vegetable beds stands ready for summer feasts with family and friends. Strings of lights will provide soft lighting after sunset to this marvelous outdoor room.
Having walked around the site, I made my way back to the front porch to begin my tour of the interiors. The wide vented door in a deep cranberry color is surrounded by half paneled, half glass sidelights and a full transom. I admired the earth tones of the exteriors with the cranberry color repeated as the header and sill trim for the windows, the light green lap siding and dark shutters. The porch’s exposed decking painted in the Southern tradition of light blue is accentuated by the exposed white rafters and the ceiling geometry of the hipped roof.
The front door opens into the stair hall with its beautiful wood floors, crisp white trim and a soft wall color as a background for the art. The original door’s picture pane above the two-panel part of the door both maintains a view of the streetscape and also provides daylight for the stair hall.
The stair is detailed with white risers that accentuate the dark balustrade and the lighter stained treads. The original door under the stair leads to a powder room tucked under stair’s landing. Simple trim and baseboards surrounds the doorway to the front parlor, with a slight overhang of the header that adds interest.
The front room is furnished as a combination parlor-formal dining room. The sofa between the front windows has a sunny view of the side yard from the window next to the fireplace. The large Oriental rug anchors the dining table and chairs and the deep wall color picks up one of the rug’s colors. The grandfather clock is an elegant finishing touch.
One step down from the front parlor/formal dining room is the 1780’s living room. I also admired this room’s warm yellow wall color that complemented the stunning hickory floors that flow through the adjacent kitchen and the family room. It would be easy to imagine sinking into the chairs for relaxing by the fire.
The Owner told me he was a retired architect as I admired his arrangement of the kitchen and how he seamlessly incorporated both the original fireplace and the long window in his design. I especially liked how well the beautiful cherry cabinets complement the bright apricot walls. The granite countertops, stainless gourmet appliances and farmhouse sink certainly pleased this cook.
As I stood in the kitchen, I admired the vista that telescoped in width from the kitchen to the family room. The offset created a wall for a window over the farmhouse kitchen sink that overlooks the brick terrace.
The large island’s oven, wine cooler and large countertop/ buffet is ready for family celebrations or entertaining large parties. The wall of pantry units with a shallow counter below the shelving with glass doors is the perfect spot for making coffee or drinks for guests.
Next to the pantry is an office with a window for respite from computer work and ample storage in the base and upper cabinets. As the Wine Woman who hosts wine tastings at Piazza Italian Market on Friday and Saturday, I was glad to see the overflow wine storage rack!
Behind the office, a wall opening between the kitchen and the living room leads to the side entry off the driveway for easy unloading groceries or shopping, with closets for coats, service equipment and the laundry room. These spaces are located in the one story part of the house dating from 1780 when they were a shed roofed open porch.
The family room’s double sliding door units creates easy indoor-outdoor flow to the rear brick terrace. Opposite the fireplace/ TV is a higher triple window unit for privacy. Another colorful rug and comfortable upholstered furnishings makes this a cozy room for relaxing at the end of the day and enjoying the long vista through the doors to the hedge at the end of the brick terrace.
I can’t resist photos of stairs from their landings and this stair’s unequal run that creates headroom for the powder room below has a vista down to the closed vented door and the open original wood door. The graceful curvature of the stair’s cap rail as it transitions to the lower run’s rail is the work of a master woodworker.
The “U” shaped stair to the second floor has an intermediate landing with a door to the primary ensuite at the rear of the house. The hall to the primary bedroom becomes a dressing room with walls of closets and a tall drawer unit. Skylights and windows in the hall provide ample daylight. The “his” and hers” three-piece bathrooms have identical layouts and windows.
The primary bedroom is located over the kitchen and its three exterior walls that gives it maximum privacy. The single windows at each side that rise to the spring line of the ceiling and the exposed stained wood rafters with their hand hewn marks give this room great interior architectural character. The trio of windows below the single window above add a contemporary accent. The deep green walls and the rugs’ complementary red colors along with the bedding creates a serene retreat.
The short run of the stair leads to the guest ensuite at the front corner of the house with windows on the two exterior walls and a fireplace. If I were a lucky guest, I would hope to stay in this guest bedroom with its interior design of the warm blue wall color, curvaceous iron bedframe, colorful coverlet and the large Oriental rug.
The stair continues to the third floor that contains this spacious guest ensuite with two windows at the front wall and one window at the rear wall for bird’s eye views of Chestertown’s rooftops and treetops. The size of the room easily accommodates the two twin beds combined into a king size bed or they could be separated per a guest’s preference.
This move-in ready property in the heart of Chestertown’s Historic District is unique in many ways. Its deep lot has off-street parking on a long driveway and a two-car garage with storage above; the outdoor rooms of the front porch for interacting with neighbors and the fenced rear brick terrace for privacy to relax with family or friends extend your warm weather living space. The fully renovated house (rewired and replumbed) with updated kitchen and baths combines the charm of its 18th & 19th century roots with state of the art environmental features including an owned by owner 8.2 kw solar array system on the garage roof, rain chains and barrels instead of downspouts and an EV level 2 charger that would enable this “green” house to obtain a Gold LEED rating. All this and a basement with a Rinnai gas water heater, other equipment, an extra refrigerator, and shelving for storage. Bravo to the Owner for his beautiful interior architecture and interior design- I especially admired his wall color choices!
For more information about this property, contact Lisa Raffetto, BAAR Recipient of 2025 Lifetime Achievement Award; BAAR 2017 J. Hurst Purnell Integrity Award and Multi-Year Coldwell Banker Sales Award Winner, with Coldwell Banker Chesapeake Real Estate Company at 410-778-0330 (o), 410-708-0174 (c) orlisar@cbchesapeake.com . For more photographs and pricing, visit www.cbchesapeake.com, “Equal Housing Opportunity.”
Open House: Saturday, May 30, 10:00 AM to 1:00 PM
Photography by Micala Dorrell, momentsbymicala.mypixieset.com
