September 13, 2026
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Design with Jenn Martella: Historic Rebuild in Chestertown

An aerial view highlights the home’s proximity to the Chester River and the historic streetscape of Chestertown.

The first time I drove across the bridge over the Chester River to Chestertown, the houses on Water Street whose back yards sloped down to the river reminded me of Charleston, SC.  One of my fave writers, Bill Bryson, included Chestertown in his 1989 book, “The Lost Continent: Travels in Small Town America”. His quest was to discover the perfect small town and his previous stop had been Charleston. It was no surprise that he succumbed to Chestertown’s charm too: “The whole place was as neat as a pin. The sidewalks were paved with brick and lined with trees and there was a well-tended park in the middle of the business district. The library was busy…” Everything Bryson admired is still the same and Washington College adds a great vibe to this charming historic town. 

This three-story home with a cozy deck offers privacy and river views, surrounded by mature trees and a vacant lot.

Today’s featured property is located close to the Chester River and the three-story house with a one-story main floor wing is next to a vacant lot that provides privacy. Above the roof of part of the one-story wing is a cozy deck for views of the river. The deck’s structure can support a hot tub and the deck’s side walls and mature trees at the rear of the property provide privacy.  

The home’s rebuilt historic design blends seamlessly into Water Street’s picturesque streetscape.

The streetscape shows how this one-bay wide, four to seven bay deep and one to three stories tall rebuilt historic house blends seamlessly into the streetscape. Its width, massing and materials of an exposed brick foundation, hipped porch roof with exposed rafters, lap siding and architectural roofing shingles enables the house to proudly reclaim it place in the streetscape. At the side of the house, a brick sidewalk leads to steps up to the front porch and also continues along the side of the house to an accessory structure at the rear of the property.

Hardwood floors and plantation shutters create a timeless living-dining space with natural light and privacy.

The front door opens into an alcove opposite the stair to the second floor and into the living-dining area. The beautiful hardwood floors flow into the adjacent rooms and the front windows overlooking the front porch and the street have plantation shutters that can be adjusted for privacy. The wood stove is a sculptural element that must have been especially appreciated during the record low temperatures we have endured recently.

A blank slate of white walls offers plenty of creative options to personalize this compact powder room.

A short hall past the living room contains this power room opposite the laundry closet. The white walls are a blank slate for one to add wallpaper, beadboard wainscot or another paint color one might prefer. 

Deep teal cabinetry anchors the spacious kitchen with its inviting breakfast nook and bright, airy views.

The short hall ends at the kitchen with its window that offers a long vista over the vacant lot next door. I admired the deep teal cabinetry with white countertops and the cozy breakfast area under the window with its deep teal support panels with top and bottom curves and the accent of the wood top. The open shelf unit above the breakfast area provides storage for wine, spirits and glasses.     

Vintage details like the stove and open shelving maintain charm while maximizing function.

The vintage stove is an unexpected treasure and the open shelving instead of upper cabinets maintains the spatial volume. The window over the sink overlooks the adjacent breezeway accessed by a door next to the stove. 

This enclosed breezeway expands the home’s floor plan, offering options for informal dining or entertaining.

An addition to the original three-story house created an enclosed breezeway that is furnished as an informal dining area. With some modifications, this could become a dining room so the living-dining area at the front of the house could become solely a living room. 

Wide windows brighten this flexible space, perfect for music, sitting areas, or expanding the breezeway.

Behind the enclosed breezeway is this room with wide windows on its side walls.  Furnished as a music room, it could also become a sitting room for the adjacent bedroom ensuite. Another option would be to combine this room with the breezeway to create a large family room with a breakfast area.

A sunny ensuite bedroom on the main floor provides aging-in-place accommodation and garden views.

A main floor ensuite is always a plus for aging-in place and this main floor bedroom has both a triple window unit on one side wall and a double unit window on the opposite wall for sunlight throughout the day. I love quilts and I admired this beautiful quilt similar to the log cabin pattern with its border of complimentary colors. 

Compact bath features neutral tones, offering a clean palette for personalization.

The main floor bedroom’s bath has both a wood lavatory and surface mounted medicine cabinet as accents to the white color of the tub, toilet and walls. 

This versatile space provides views over Chestertown’s historic streetscape and the Chester River beyond.

The second floor contains two bedrooms, a bath and the stair to the third floor. The compact floor plan works very well with the stair landing blending into a short hall past the hall bath and the stair to the third floor. This bedroom that is furnished as a den has windows overlooking the street below and bird’s eye views of the river. 

Thoughtful design maximizes space while crisp white finishes amplify the sense of openness.

The hall bath’s white surfaces and compact arrangement makes it seem larger than it is. The splash of blue in the shower curtain and towels is a colorful accent.

This light-filled room with deck access creates a serene workspace or a second-floor bedroom retreat.

The rear bedroom is furnished as a workroom and the rolls of colorful fabric await their turn to become parts of future quilts. The exterior door leads to the deck for a break from work and a low door in the one-story addition leads to attic storage.  Two closets provide more storage. The French door, single window and another window at the side wall provide ample daylight.

Quiet and spacious, this third-floor ensuite is enhanced by soft textures and colorful, handcrafted bedding.

The third floor contains only the primary ensuite for privacy and I loved the colorful quilt in the Dresden Plate pattern and scalloped edging to enhance the design. The spacious room has sleeping and sitting areas and the thin bedframe maintains the spatial volume. 

The dormer window in the hallway frames treetop views, adding charm to this functional design.

From the primary bedroom, a short hall past the walk-in closet and the bathroom ends at the front double unit window in the dormer overlooking the street. There is ample room underneath the windows for a settee or a chest  of drawers.  The carpet muffles sound to the second floor rooms below. What wonderful bird’s eye views of the treetops, rooftops and the Chester River the window must offer! 

Compact yet elegant, the primary bath’s neutral palette offers flexibility for personalized décor.

The primary bath is compact and like the other bathrooms, the neutral palette in shades of white offer a blank slate for one’s color accents. 

The accessory structure near the back of the property boasts versatile design and sunny interiors.

The brick path along the side of the house expands to infill the space between the house and the accessory structure near the rear property line. The half glass, half paneled doors and the windows create a sunny interior space with myriad uses.

A spacious workshop ready for transformation into a screened pavilion or expanded outdoor entertaining space.

The spacious accessory structure is currently used as a workshop. If this were my property, I would be tempted to modify the walls to create a screened outdoor pavilion to expand the outdoor living space. 

This move-in ready home in Chestertown’s Historic District is a rare opportunity to enjoy a newly renovated historic house with close proximity to both the Chester River and Chestertown’s shops, restaurants and other amenities. The outdoor rooms of the front porch and second floor deck offer views of the water. Bedrooms and baths on all three floors offer both aging in place and privacy for guests. Neutral finishes enable one to add their own color choices,  plantation shutters are the perfect window treatments for flexible privacy and handcrafted cabinetry adds charm. To quote Bill Bryson, “The whole place was as neat as a pin…!


For more information about this property, contact Tom Williams, Vice President/Realtor with TTR Sotheby’s International Realty at 410-673-3344 (o), 202-255-3650 (c), or   tomwilliams@ttrsir.comFor more pictures and pricing, visit https://www.sothebysrealty.com/ttrsir/eng/associate/766-a-df230307162710858982/tom-williams,“Equal Housing Opportunity”.

Photography by Steve Buchanan Photography, 301-996-7295, www.buchananphotography.com .

The Lost Continent: Travels in Small Town America” by Bill Bryson, originally  published by Harper & Row

Contributor Jennifer Martella has pursued dual careers in architecture and real estate since she moved to the Eastern Shore in 2004. She has reestablished her architectural practice for residential and commercial projects and is a real estate agent for Meredith Fine Properties. She especially enjoys using her architectural expertise to help buyers envision how they could modify a potential property. Her Italian heritage led her to Piazza Italian Market, where she hosts wine tastings every Friday and Saturday afternoons.

AI Disclosure: The Spy and its writers may use artificial intelligence tools to support accuracy and clarity in our reporting.

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